Merge pull request #884 from vmware-tanzu/upstream-ad-refresh

Upstream active directory refresh checks for password changes, deactivated and locked users

internal/authenticators/authenticators.go

@@ -37,4 +37,5 @@ type UserAuthenticator interface {
 type Response struct {
 	User                   user.Info
 	DN                     string
+	ExtraRefreshAttributes map[string]string
 }

internal/controller/supervisorconfig/activedirectoryupstreamwatcher/active_directory_upstream_watcher.go

@@ -7,8 +7,12 @@ package activedirectoryupstreamwatcher
 import (
 	"context"
 	"fmt"
+	"regexp"
+	"strconv"
+	"strings"
 
 	"github.com/go-ldap/ldap/v3"
+	"github.com/google/uuid"
 
 	"k8s.io/apimachinery/pkg/api/equality"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
@@ -52,6 +56,21 @@ const (
 	// - has a member that matches the DN of the user we successfully logged in as.
 	// - perform nested group search by default.
 	defaultActiveDirectoryGroupSearchFilter = "(&(objectClass=group)(member:1.2.840.113556.1.4.1941:={}))"
+
+	sAMAccountNameAttribute = "sAMAccountName"
+	// PwdLastSetAttribute is the date and time that the password for this account was last changed.
+	// https://docs.microsoft.com/en-us/windows/win32/adschema/a-pwdlastset
+	PwdLastSetAttribute = "pwdLastSet"
+	// UserAccountControlAttribute represents a bitmap of user properties.
+	// https://docs.microsoft.com/en-us/troubleshoot/windows-server/identity/useraccountcontrol-manipulate-account-properties
+	UserAccountControlAttribute = "userAccountControl"
+	// UserAccountControlComputedAttribute represents a bitmap of user properties.
+	// https://docs.microsoft.com/en-us/windows/win32/adschema/a-msds-user-account-control-computed
+	UserAccountControlComputedAttribute = "msDS-User-Account-Control-Computed"
+	// 0x0002 ACCOUNTDISABLE in userAccountControl bitmap.
+	accountDisabledBitmapValue = 2
+	// 0x0010 UF_LOCKOUT in msDS-User-Account-Control-Computed bitmap.
+	accountLockedBitmapValue = 16
 )
 
 type activeDirectoryUpstreamGenericLDAPImpl struct {
@@ -316,11 +335,16 @@ func (c *activeDirectoryWatcherController) validateUpstream(ctx context.Context,
 			GroupNameAttribute: adUpstreamImpl.Spec().GroupSearch().GroupNameAttribute(),
 		},
 		Dialer:                       c.ldapDialer,
-		UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+		UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+		RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+			PwdLastSetAttribute:                 upstreamldap.AttributeUnchangedSinceLogin(PwdLastSetAttribute),
+			UserAccountControlAttribute:         ValidUserAccountControl,
+			UserAccountControlComputedAttribute: ValidComputedUserAccountControl,
+		},
 	}
 
 	if spec.GroupSearch.Attributes.GroupName == "" {
-		config.GroupAttributeParsingOverrides = map[string]func(*ldap.Entry) (string, error){defaultActiveDirectoryGroupNameAttributeName: upstreamldap.GroupSAMAccountNameWithDomainSuffix}
+		config.GroupAttributeParsingOverrides = map[string]func(*ldap.Entry) (string, error){defaultActiveDirectoryGroupNameAttributeName: GroupSAMAccountNameWithDomainSuffix}
 	}
 
 	conditions := upstreamwatchers.ValidateGenericLDAP(ctx, adUpstreamImpl, c.secretInformer, c.validatedSecretVersionsCache, config)
@@ -353,3 +377,84 @@ func (c *activeDirectoryWatcherController) updateStatus(ctx context.Context, ups
 		log.Error(err, "failed to update status")
 	}
 }
+
+func MicrosoftUUIDFromBinary(attributeName string) func(entry *ldap.Entry) (string, error) {
+	// validation has already been done so we can just get the attribute...
+	return func(entry *ldap.Entry) (string, error) {
+		binaryUUID := entry.GetRawAttributeValue(attributeName)
+		return microsoftUUIDFromBinary(binaryUUID)
+	}
+}
+
+func microsoftUUIDFromBinary(binaryUUID []byte) (string, error) {
+	uuidVal, err := uuid.FromBytes(binaryUUID) // start out with the RFC4122 version
+	if err != nil {
+		return "", err
+	}
+	// then swap it because AD stores the first 3 fields little-endian rather than the expected
+	// big-endian.
+	uuidVal[0], uuidVal[1], uuidVal[2], uuidVal[3] = uuidVal[3], uuidVal[2], uuidVal[1], uuidVal[0]
+	uuidVal[4], uuidVal[5] = uuidVal[5], uuidVal[4]
+	uuidVal[6], uuidVal[7] = uuidVal[7], uuidVal[6]
+	return uuidVal.String(), nil
+}
+
+func GroupSAMAccountNameWithDomainSuffix(entry *ldap.Entry) (string, error) {
+	sAMAccountNameAttributeValues := entry.GetAttributeValues(sAMAccountNameAttribute)
+
+	if len(sAMAccountNameAttributeValues) != 1 {
+		return "", fmt.Errorf(`found %d values for attribute "%s", but expected 1 result`,
+			len(sAMAccountNameAttributeValues), sAMAccountNameAttribute,
+		)
+	}
+
+	sAMAccountName := sAMAccountNameAttributeValues[0]
+	if len(sAMAccountName) == 0 {
+		return "", fmt.Errorf(`found empty value for attribute "%s", but expected value to be non-empty`,
+			sAMAccountNameAttribute,
+		)
+	}
+
+	distinguishedName := entry.DN
+	domain, err := getDomainFromDistinguishedName(distinguishedName)
+	if err != nil {
+		return "", err
+	}
+	return sAMAccountName + "@" + domain, nil
+}
+
+var domainComponentsRegexp = regexp.MustCompile(",DC=|,dc=")
+
+func getDomainFromDistinguishedName(distinguishedName string) (string, error) {
+	domainComponents := domainComponentsRegexp.Split(distinguishedName, -1)
+	if len(domainComponents) == 1 {
+		return "", fmt.Errorf("did not find domain components in group dn: %s", distinguishedName)
+	}
+	return strings.Join(domainComponents[1:], "."), nil
+}
+
+func ValidUserAccountControl(entry *ldap.Entry, _ provider.StoredRefreshAttributes) error {
+	userAccountControl, err := strconv.Atoi(entry.GetAttributeValue(UserAccountControlAttribute))
+	if err != nil {
+		return err
+	}
+
+	deactivated := userAccountControl & accountDisabledBitmapValue // bitwise and.
+	if deactivated != 0 {
+		return fmt.Errorf("user has been deactivated")
+	}
+	return nil
+}
+
+func ValidComputedUserAccountControl(entry *ldap.Entry, _ provider.StoredRefreshAttributes) error {
+	userAccountControl, err := strconv.Atoi(entry.GetAttributeValue(UserAccountControlComputedAttribute))
+	if err != nil {
+		return err
+	}
+
+	locked := userAccountControl & accountLockedBitmapValue // bitwise and
+	if locked != 0 {
+		return fmt.Errorf("user has been locked")
+	}
+	return nil
+}

internal/controller/supervisorconfig/activedirectoryupstreamwatcher/active_directory_upstream_watcher_test.go

@@ -220,7 +220,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 			Filter:             testGroupSearchFilter,
 			GroupNameAttribute: testGroupNameAttrName,
 		},
-		UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+		UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+		RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+			"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+			"userAccountControl":                 ValidUserAccountControl,
+			"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+		},
 	}
 
 	// Make a copy with targeted changes.
@@ -536,7 +541,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -592,7 +602,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: "sAMAccountName",
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -651,7 +666,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -710,7 +730,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantErr: controllerlib.ErrSyntheticRequeue.Error(),
@@ -768,7 +793,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -897,7 +927,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -1021,8 +1056,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
-				},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					}},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
 				ObjectMeta: metav1.ObjectMeta{Namespace: testNamespace, Name: testName, UID: testResourceUID, Generation: 1234},
@@ -1072,7 +1111,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -1271,8 +1315,13 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             "(&(objectClass=group)(member:1.2.840.113556.1.4.1941:={}))",
 						GroupNameAttribute: "sAMAccountName",
 					},
-					UIDAttributeParsingOverrides:   map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides:   map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
-					GroupAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"sAMAccountName": upstreamldap.GroupSAMAccountNameWithDomainSuffix},
+					GroupAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"sAMAccountName": GroupSAMAccountNameWithDomainSuffix},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -1324,7 +1373,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -1380,7 +1434,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -1430,7 +1489,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -1626,7 +1690,12 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 						Filter:             testGroupSearchFilter,
 						GroupNameAttribute: testGroupNameAttrName,
 					},
-					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": upstreamldap.MicrosoftUUIDFromBinary("objectGUID")},
+					UIDAttributeParsingOverrides: map[string]func(*ldap.Entry) (string, error){"objectGUID": MicrosoftUUIDFromBinary("objectGUID")},
+					RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+						"pwdLastSet":                         upstreamldap.AttributeUnchangedSinceLogin("pwdLastSet"),
+						"userAccountControl":                 ValidUserAccountControl,
+						"msDS-User-Account-Control-Computed": ValidComputedUserAccountControl,
+					},
 				},
 			},
 			wantResultingUpstreams: []v1alpha1.ActiveDirectoryIdentityProvider{{
@@ -1753,6 +1822,16 @@ func TestActiveDirectoryUpstreamWatcherControllerSync(t *testing.T) {
 					require.Equal(t, reflect.ValueOf(v).Pointer(), reflect.ValueOf(actualGroupAttributeParsingOverrides[k]).Pointer())
 				}
 
+				expectedRefreshAttributeChecks := copyOfExpectedValueForResultingCache.RefreshAttributeChecks
+				actualRefreshAttributeChecks := actualConfig.RefreshAttributeChecks
+				copyOfExpectedValueForResultingCache.RefreshAttributeChecks = map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{}
+				actualConfig.RefreshAttributeChecks = map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{}
+				require.Equal(t, len(expectedRefreshAttributeChecks), len(actualRefreshAttributeChecks))
+				for k, v := range expectedRefreshAttributeChecks {
+					require.NotNil(t, actualRefreshAttributeChecks[k])
+					require.Equal(t, reflect.ValueOf(v).Pointer(), reflect.ValueOf(actualRefreshAttributeChecks[k]).Pointer())
+				}
+
 				require.Equal(t, copyOfExpectedValueForResultingCache, actualConfig)
 			}
 
@@ -1800,3 +1879,270 @@ func normalizeActiveDirectoryUpstreams(upstreams []v1alpha1.ActiveDirectoryIdent
 
 	return result
 }
+
+func TestGroupSAMAccountNameWithDomainSuffix(t *testing.T) {
+	tests := []struct {
+		name       string
+		entry      *ldap.Entry
+		wantResult string
+		wantErr    string
+	}{
+		{
+			name: "happy path with DN and valid sAMAccountName",
+			entry: &ldap.Entry{
+				DN: "CN=animals,OU=Users,OU=pinniped-ad,DC=mycompany,DC=example,DC=com",
+				Attributes: []*ldap.EntryAttribute{
+					ldap.NewEntryAttribute("sAMAccountName", []string{"Mammals"}),
+				},
+			},
+			wantResult: "Mammals@mycompany.example.com",
+		},
+		{
+			name: "no domain components in DN",
+			entry: &ldap.Entry{
+				DN: "no-domain-components",
+				Attributes: []*ldap.EntryAttribute{
+					ldap.NewEntryAttribute("sAMAccountName", []string{"Mammals"}),
+				},
+			},
+			wantErr: "did not find domain components in group dn: no-domain-components",
+		},
+		{
+			name: "multiple values for sAMAccountName attribute",
+			entry: &ldap.Entry{
+				DN: "CN=animals,OU=Users,OU=pinniped-ad,DC=mycompany,DC=example,DC=com",
+				Attributes: []*ldap.EntryAttribute{
+					ldap.NewEntryAttribute("sAMAccountName", []string{"Mammals", "Eukaryotes"}),
+				},
+			},
+			wantErr: "found 2 values for attribute \"sAMAccountName\", but expected 1 result",
+		},
+		{
+			name: "no values for sAMAccountName attribute",
+			entry: &ldap.Entry{
+				DN: "CN=animals,OU=Users,OU=pinniped-ad,DC=mycompany,DC=example,DC=com",
+				Attributes: []*ldap.EntryAttribute{
+					ldap.NewEntryAttribute("sAMAccountName", []string{}),
+				},
+			},
+			wantErr: "found 0 values for attribute \"sAMAccountName\", but expected 1 result",
+		},
+	}
+	for _, test := range tests {
+		tt := test
+		t.Run(tt.name, func(t *testing.T) {
+			suffixedSAMAccountName, err := GroupSAMAccountNameWithDomainSuffix(tt.entry)
+			if tt.wantErr != "" {
+				require.EqualError(t, err, tt.wantErr)
+			} else {
+				require.NoError(t, err)
+			}
+			require.Equal(t, tt.wantResult, suffixedSAMAccountName)
+		})
+	}
+}
+
+func TestGetMicrosoftFormattedUUID(t *testing.T) {
+	tests := []struct {
+		name       string
+		binaryUUID []byte
+		wantString string
+		wantErr    string
+	}{
+		{
+			name:       "happy path",
+			binaryUUID: []byte("\x01\x02\x03\x04\x05\x06\x07\x08\x09\x10\x11\x12\x13\x14\x15\x16"),
+			wantString: "04030201-0605-0807-0910-111213141516",
+		},
+		{
+			name:       "not the right length",
+			binaryUUID: []byte("2\xf8\xb0\xaa\xb6V\xb1D\x8b(\xee"),
+			wantErr:    "invalid UUID (got 11 bytes)",
+		},
+	}
+
+	for _, test := range tests {
+		tt := test
+		t.Run(tt.name, func(t *testing.T) {
+			actualUUIDString, err := microsoftUUIDFromBinary(tt.binaryUUID)
+			if tt.wantErr != "" {
+				require.EqualError(t, err, tt.wantErr)
+			} else {
+				require.NoError(t, err)
+			}
+			require.Equal(t, tt.wantString, actualUUIDString)
+		})
+	}
+}
+
+func TestGetDomainFromDistinguishedName(t *testing.T) {
+	tests := []struct {
+		name              string
+		distinguishedName string
+		wantDomain        string
+		wantErr           string
+	}{
+		{
+			name:              "happy path",
+			distinguishedName: "CN=Mammals,OU=Users,OU=pinniped-ad,DC=activedirectory,DC=mycompany,DC=example,DC=com",
+			wantDomain:        "activedirectory.mycompany.example.com",
+		},
+		{
+			name:              "lowercased happy path",
+			distinguishedName: "cn=Mammals,ou=Users,ou=pinniped-ad,dc=activedirectory,dc=mycompany,dc=example,dc=com",
+			wantDomain:        "activedirectory.mycompany.example.com",
+		},
+		{
+			name:              "no domain components",
+			distinguishedName: "not-a-dn",
+			wantErr:           "did not find domain components in group dn: not-a-dn",
+		},
+	}
+
+	for _, test := range tests {
+		tt := test
+		t.Run(tt.name, func(t *testing.T) {
+			actualDomain, err := getDomainFromDistinguishedName(tt.distinguishedName)
+			if tt.wantErr != "" {
+				require.EqualError(t, err, tt.wantErr)
+			} else {
+				require.NoError(t, err)
+			}
+			require.Equal(t, tt.wantDomain, actualDomain)
+		})
+	}
+}
+
+func TestValidUserAccountControl(t *testing.T) {
+	tests := []struct {
+		name    string
+		entry   *ldap.Entry
+		wantErr string
+	}{
+		{
+			name: "happy normal user",
+			entry: &ldap.Entry{
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:   "userAccountControl",
+						Values: []string{"512"},
+					},
+				},
+			},
+		},
+		{
+			name: "happy user whose password doesn't expire",
+			entry: &ldap.Entry{
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:   "userAccountControl",
+						Values: []string{"65536"},
+					},
+				},
+			},
+		},
+		{
+			name: "deactivated user",
+			entry: &ldap.Entry{
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:   "userAccountControl",
+						Values: []string{"514"},
+					},
+				},
+			},
+			wantErr: "user has been deactivated",
+		},
+		{
+			name: "non-integer result",
+			entry: &ldap.Entry{
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:   "userAccountControl",
+						Values: []string{"not-an-int"},
+					},
+				},
+			},
+			wantErr: "strconv.Atoi: parsing \"not-an-int\": invalid syntax",
+		},
+	}
+
+	for _, test := range tests {
+		tt := test
+		t.Run(tt.name, func(t *testing.T) {
+			err := ValidUserAccountControl(tt.entry, provider.StoredRefreshAttributes{})
+
+			if tt.wantErr != "" {
+				require.Error(t, err)
+				require.Equal(t, tt.wantErr, err.Error())
+			} else {
+				require.NoError(t, err)
+			}
+		})
+	}
+}
+
+func TestValidComputedUserAccountControl(t *testing.T) {
+	tests := []struct {
+		name    string
+		entry   *ldap.Entry
+		wantErr string
+	}{
+		{
+			name: "happy normal user",
+			entry: &ldap.Entry{
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:   "msDS-User-Account-Control-Computed",
+						Values: []string{"0"},
+					},
+				},
+			},
+		},
+		{
+			name: "locked user",
+			entry: &ldap.Entry{
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:   "msDS-User-Account-Control-Computed",
+						Values: []string{"16"},
+					},
+				},
+			},
+			wantErr: "user has been locked",
+		},
+		{
+			name: "non-integer result",
+			entry: &ldap.Entry{
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:   "msDS-User-Account-Control-Computed",
+						Values: []string{"not-an-int"},
+					},
+				},
+			},
+			wantErr: "strconv.Atoi: parsing \"not-an-int\": invalid syntax",
+		},
+	}
+
+	for _, test := range tests {
+		tt := test
+		t.Run(tt.name, func(t *testing.T) {
+			err := ValidComputedUserAccountControl(tt.entry, provider.StoredRefreshAttributes{})
+
+			if tt.wantErr != "" {
+				require.Error(t, err)
+				require.Equal(t, tt.wantErr, err.Error())
+			} else {
+				require.NoError(t, err)
+			}
+		})
+	}
+}

internal/fositestorage/authorizationcode/authorizationcode.go

@@ -348,20 +348,25 @@ const ExpectedAuthorizeCodeSessionJSONFromFuzzing = `{
 					"upstreamRefreshToken": "嵽痊w©Ź榨Q|ôɵt毇妬"
 				},
 				"ldap": {
-					"userDN": "6鉢緋uƴŤȱʀļÂ?墖\u003cƬb獭潜Ʃ饾"
+					"userDN": "6鉢緋uƴŤȱʀļÂ?墖\u003cƬb獭潜Ʃ饾",
+					"extraRefreshAttributes": {
+						"ď逳鞪?3)藵睋邔\u0026Ű惫蜀Ģ¡圔": "墀jMʥ",
+						"齁š%OpKȱ藚ɏ¬Ê蒭堜]ȗ韚ʫ": "鷞aŚB碠k9帴ʘ赱"
+					}
 				},
 				"activedirectory": {
-					"userDN": "|鬌R蜚蠣麹概÷驣7Ʀ澉1æɽ誮rʨ鷞"
+					"userDN": "0D餹sêĝɓ",
+					"extraRefreshAttributes": {
+						"摱ì": "bEǎ儯惝Io"
+					}
 				}
 			}
 		},
 		"requestedAudience": [
-			"ŚB碠k9"
+			"Ł"
 		],
 		"grantedAudience": [
-			"ʘ赱",
+			"r"
-			"ď逳鞪?3)藵睋邔\u0026Ű惫蜀Ģ¡圔",
-			"墀jMʥ"
 		]
 	},
 	"version": "2"

internal/oidc/auth/auth_handler.go

@@ -123,11 +123,13 @@ func handleAuthRequestForLDAPUpstream(
 	if idpType == psession.ProviderTypeLDAP {
 		customSessionData.LDAP = &psession.LDAPSessionData{
 			UserDN:                 dn,
+			ExtraRefreshAttributes: authenticateResponse.ExtraRefreshAttributes,
 		}
 	}
 	if idpType == psession.ProviderTypeActiveDirectory {
 		customSessionData.ActiveDirectory = &psession.ActiveDirectorySessionData{
 			UserDN:                 dn,
+			ExtraRefreshAttributes: authenticateResponse.ExtraRefreshAttributes,
 		}
 	}
 

internal/oidc/auth/auth_handler_test.go

@@ -269,6 +269,8 @@ func TestAuthorizationEndpoint(t *testing.T) {
 	happyLDAPUID := "some-ldap-uid"
 	happyLDAPUserDN := "cn=foo,dn=bar"
 	happyLDAPGroups := []string{"group1", "group2", "group3"}
+	happyLDAPExtraRefreshAttribute := "some-refresh-attribute"
+	happyLDAPExtraRefreshValue := "some-refresh-attribute-value"
 
 	parsedUpstreamLDAPURL, err := url.Parse(upstreamLDAPURL)
 	require.NoError(t, err)
@@ -285,6 +287,9 @@ func TestAuthorizationEndpoint(t *testing.T) {
 					Groups: happyLDAPGroups,
 				},
 				DN: happyLDAPUserDN,
+				ExtraRefreshAttributes: map[string]string{
+					happyLDAPExtraRefreshAttribute: happyLDAPExtraRefreshValue,
+				},
 			}, true, nil
 		}
 		return nil, false, nil
@@ -443,6 +448,7 @@ func TestAuthorizationEndpoint(t *testing.T) {
 		LDAP:         nil,
 		ActiveDirectory: &psession.ActiveDirectorySessionData{
 			UserDN:                 happyLDAPUserDN,
+			ExtraRefreshAttributes: map[string]string{happyLDAPExtraRefreshAttribute: happyLDAPExtraRefreshValue},
 		},
 	}
 
@@ -453,6 +459,7 @@ func TestAuthorizationEndpoint(t *testing.T) {
 		OIDC:         nil,
 		LDAP: &psession.LDAPSessionData{
 			UserDN:                 happyLDAPUserDN,
+			ExtraRefreshAttributes: map[string]string{happyLDAPExtraRefreshAttribute: happyLDAPExtraRefreshValue},
 		},
 		ActiveDirectory: nil,
 	}

internal/oidc/provider/dynamic_upstream_idp_provider.go

@@ -7,6 +7,7 @@ import (
 	"context"
 	"net/url"
 	"sync"
+	"time"
 
 	"golang.org/x/oauth2"
 	"k8s.io/apimachinery/pkg/types"
@@ -93,7 +94,15 @@ type UpstreamLDAPIdentityProviderI interface {
 	authenticators.UserAuthenticator
 
 	// PerformRefresh performs a refresh against the upstream LDAP identity provider
-	PerformRefresh(ctx context.Context, userDN, expectedUsername, expectedSubject string) error
+	PerformRefresh(ctx context.Context, storedRefreshAttributes StoredRefreshAttributes) error
+}
+
+type StoredRefreshAttributes struct {
+	Username             string
+	Subject              string
+	DN                   string
+	AuthTime             time.Time
+	AdditionalAttributes map[string]string
 }
 
 type DynamicUpstreamIDPProvider interface {

internal/oidc/token/token_handler.go

@@ -75,11 +75,6 @@ func NewHandler(
 
 func upstreamRefresh(ctx context.Context, accessRequest fosite.AccessRequester, providerCache oidc.UpstreamIdentityProvidersLister) error {
 	session := accessRequest.GetSession().(*psession.PinnipedSession)
-	downstreamUsername, err := getDownstreamUsernameFromPinnipedSession(session)
-	if err != nil {
-		return err
-	}
-	downstreamSubject := session.Fosite.Claims.Subject
 
 	customSessionData := session.Custom
 	if customSessionData == nil {
@@ -95,9 +90,9 @@ func upstreamRefresh(ctx context.Context, accessRequest fosite.AccessRequester,
 	case psession.ProviderTypeOIDC:
 		return upstreamOIDCRefresh(ctx, customSessionData, providerCache)
 	case psession.ProviderTypeLDAP:
-		return upstreamLDAPRefresh(ctx, customSessionData, providerCache, downstreamUsername, downstreamSubject)
+		return upstreamLDAPRefresh(ctx, providerCache, session)
 	case psession.ProviderTypeActiveDirectory:
-		return upstreamLDAPRefresh(ctx, customSessionData, providerCache, downstreamUsername, downstreamSubject)
+		return upstreamLDAPRefresh(ctx, providerCache, session)
 	default:
 		return errorsx.WithStack(errMissingUpstreamSessionInternalError)
 	}
@@ -169,7 +164,15 @@ func findOIDCProviderByNameAndValidateUID(
 		WithHint("Provider from upstream session data was not found.").WithDebugf("provider name: %q, provider type: %q", s.ProviderName, s.ProviderType))
 }
 
-func upstreamLDAPRefresh(ctx context.Context, s *psession.CustomSessionData, providerCache oidc.UpstreamIdentityProvidersLister, username string, subject string) error {
+func upstreamLDAPRefresh(ctx context.Context, providerCache oidc.UpstreamIdentityProvidersLister, session *psession.PinnipedSession) error {
+	username, err := getDownstreamUsernameFromPinnipedSession(session)
+	if err != nil {
+		return err
+	}
+	subject := session.Fosite.Claims.Subject
+
+	s := session.Custom
+
 	// if you have neither a valid ldap session config nor a valid active directory session config
 	validLDAP := s.ProviderType == psession.ProviderTypeLDAP && s.LDAP != nil && s.LDAP.UserDN != ""
 	validAD := s.ProviderType == psession.ProviderTypeActiveDirectory && s.ActiveDirectory != nil && s.ActiveDirectory.UserDN != ""
@@ -177,13 +180,28 @@ func upstreamLDAPRefresh(ctx context.Context, s *psession.CustomSessionData, pro
 		return errorsx.WithStack(errMissingUpstreamSessionInternalError)
 	}
 
+	var additionalAttributes map[string]string
+	if s.ProviderType == psession.ProviderTypeLDAP {
+		additionalAttributes = s.LDAP.ExtraRefreshAttributes
+	} else {
+		additionalAttributes = s.ActiveDirectory.ExtraRefreshAttributes
+	}
+
 	// get ldap/ad provider out of cache
 	p, dn, err := findLDAPProviderByNameAndValidateUID(s, providerCache)
 	if err != nil {
 		return err
 	}
+	if session.IDTokenClaims().AuthTime.IsZero() {
+		return errorsx.WithStack(errMissingUpstreamSessionInternalError)
+	}
 	// run PerformRefresh
-	err = p.PerformRefresh(ctx, dn, username, subject)
+	err = p.PerformRefresh(ctx, provider.StoredRefreshAttributes{
+		Username:             username,
+		Subject:              subject,
+		DN:                   dn,
+		AdditionalAttributes: additionalAttributes,
+	})
 	if err != nil {
 		return errorsx.WithStack(errUpstreamRefreshError.WithHint(
 			"Upstream refresh failed.").WithWrap(err).WithDebugf("provider name: %q, provider type: %q", s.ProviderName, s.ProviderType))

internal/oidc/token/token_handler_test.go

@@ -2058,6 +2058,219 @@ func TestRefreshGrant(t *testing.T) {
 				},
 			},
 		},
+		{
+			name: "upstream ldap idp not found",
+			idps: oidctestutil.NewUpstreamIDPListerBuilder(),
+			authcodeExchange: authcodeExchangeInputs{
+				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },
+				customSessionData: happyLDAPCustomSessionData,
+				want: happyAuthcodeExchangeTokenResponseForOpenIDAndOfflineAccess(
+					happyLDAPCustomSessionData,
+				),
+			},
+			refreshRequest: refreshRequestInputs{
+				want: tokenEndpointResponseExpectedValues{
+					wantStatus: http.StatusUnauthorized,
+					wantErrorResponseBody: here.Doc(`
+						{
+							"error":             "error",
+							"error_description": "Error during upstream refresh. Provider from upstream session data was not found."
+						}
+					`),
+				},
+			},
+		},
+		{
+			name: "upstream active directory idp not found",
+			idps: oidctestutil.NewUpstreamIDPListerBuilder(),
+			authcodeExchange: authcodeExchangeInputs{
+				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },
+				customSessionData: happyActiveDirectoryCustomSessionData,
+				want: happyAuthcodeExchangeTokenResponseForOpenIDAndOfflineAccess(
+					happyActiveDirectoryCustomSessionData,
+				),
+			},
+			refreshRequest: refreshRequestInputs{
+				want: tokenEndpointResponseExpectedValues{
+					wantStatus: http.StatusUnauthorized,
+					wantErrorResponseBody: here.Doc(`
+						{
+							"error":             "error",
+							"error_description": "Error during upstream refresh. Provider from upstream session data was not found."
+						}
+					`),
+				},
+			},
+		},
+		{
+			name: "fosite session is empty",
+			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithLDAP(&oidctestutil.TestUpstreamLDAPIdentityProvider{
+				Name:        ldapUpstreamName,
+				ResourceUID: ldapUpstreamResourceUID,
+				URL:         ldapUpstreamURL,
+			}),
+			authcodeExchange: authcodeExchangeInputs{
+				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },
+				customSessionData: happyLDAPCustomSessionData,
+				want: happyAuthcodeExchangeTokenResponseForOpenIDAndOfflineAccess(
+					happyLDAPCustomSessionData,
+				),
+			},
+			modifyRefreshTokenStorage: func(t *testing.T, oauthStore *oidc.KubeStorage, refreshToken string) {
+				refreshTokenSignature := getFositeDataSignature(t, refreshToken)
+				firstRequester, err := oauthStore.GetRefreshTokenSession(context.Background(), refreshTokenSignature, nil)
+				require.NoError(t, err)
+				session := firstRequester.GetSession().(*psession.PinnipedSession)
+				session.Fosite = &openid.DefaultSession{}
+				err = oauthStore.DeleteRefreshTokenSession(context.Background(), refreshTokenSignature)
+				require.NoError(t, err)
+				err = oauthStore.CreateRefreshTokenSession(context.Background(), refreshTokenSignature, firstRequester)
+				require.NoError(t, err)
+			},
+			refreshRequest: refreshRequestInputs{
+				want: tokenEndpointResponseExpectedValues{
+					wantStatus: http.StatusInternalServerError,
+					wantErrorResponseBody: here.Doc(`
+						{
+							"error":             "error",
+							"error_description": "There was an internal server error. Required upstream data not found in session."
+						}
+					`),
+				},
+			},
+		},
+		{
+			name: "username not found in extra field",
+			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithLDAP(&oidctestutil.TestUpstreamLDAPIdentityProvider{
+				Name:        ldapUpstreamName,
+				ResourceUID: ldapUpstreamResourceUID,
+				URL:         ldapUpstreamURL,
+			}),
+			authcodeExchange: authcodeExchangeInputs{
+				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },
+				customSessionData: happyLDAPCustomSessionData,
+				want: happyAuthcodeExchangeTokenResponseForOpenIDAndOfflineAccess(
+					happyLDAPCustomSessionData,
+				),
+			},
+			modifyRefreshTokenStorage: func(t *testing.T, oauthStore *oidc.KubeStorage, refreshToken string) {
+				refreshTokenSignature := getFositeDataSignature(t, refreshToken)
+				firstRequester, err := oauthStore.GetRefreshTokenSession(context.Background(), refreshTokenSignature, nil)
+				require.NoError(t, err)
+				session := firstRequester.GetSession().(*psession.PinnipedSession)
+				session.Fosite = &openid.DefaultSession{
+					Claims: &jwt.IDTokenClaims{
+						Extra: map[string]interface{}{},
+					},
+				}
+				err = oauthStore.DeleteRefreshTokenSession(context.Background(), refreshTokenSignature)
+				require.NoError(t, err)
+				err = oauthStore.CreateRefreshTokenSession(context.Background(), refreshTokenSignature, firstRequester)
+				require.NoError(t, err)
+			},
+			refreshRequest: refreshRequestInputs{
+				want: tokenEndpointResponseExpectedValues{
+					wantStatus: http.StatusInternalServerError,
+					wantErrorResponseBody: here.Doc(`
+						{
+							"error":             "error",
+							"error_description": "There was an internal server error. Required upstream data not found in session."
+						}
+					`),
+				},
+			},
+		},
+		{
+			name: "auth time is the zero value", // time.Times can never be nil, but it is possible that it would be the zero value which would mean something's wrong
+			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithLDAP(&oidctestutil.TestUpstreamLDAPIdentityProvider{
+				Name:        ldapUpstreamName,
+				ResourceUID: ldapUpstreamResourceUID,
+				URL:         ldapUpstreamURL,
+			}),
+			authcodeExchange: authcodeExchangeInputs{
+				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },
+				customSessionData: happyLDAPCustomSessionData,
+				want: happyAuthcodeExchangeTokenResponseForOpenIDAndOfflineAccess(
+					happyLDAPCustomSessionData,
+				),
+			},
+			modifyRefreshTokenStorage: func(t *testing.T, oauthStore *oidc.KubeStorage, refreshToken string) {
+				refreshTokenSignature := getFositeDataSignature(t, refreshToken)
+				firstRequester, err := oauthStore.GetRefreshTokenSession(context.Background(), refreshTokenSignature, nil)
+				require.NoError(t, err)
+				session := firstRequester.GetSession().(*psession.PinnipedSession)
+				fositeSessionClaims := session.Fosite.IDTokenClaims()
+				fositeSessionClaims.AuthTime = time.Time{}
+				session.Fosite.Claims = fositeSessionClaims
+				err = oauthStore.DeleteRefreshTokenSession(context.Background(), refreshTokenSignature)
+				require.NoError(t, err)
+				err = oauthStore.CreateRefreshTokenSession(context.Background(), refreshTokenSignature, firstRequester)
+				require.NoError(t, err)
+			},
+			refreshRequest: refreshRequestInputs{
+				want: tokenEndpointResponseExpectedValues{
+					wantStatus: http.StatusInternalServerError,
+					wantErrorResponseBody: here.Doc(`
+						{
+							"error":             "error",
+							"error_description": "There was an internal server error. Required upstream data not found in session."
+						}
+					`),
+				},
+			},
+		},
+		{
+			name: "when the ldap provider in the session storage is found but has the wrong resource UID during the refresh request",
+			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithLDAP(&oidctestutil.TestUpstreamLDAPIdentityProvider{
+				Name:        ldapUpstreamName,
+				ResourceUID: "the-wrong-uid",
+				URL:         ldapUpstreamURL,
+			}),
+			authcodeExchange: authcodeExchangeInputs{
+				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },
+				customSessionData: happyLDAPCustomSessionData,
+				want: happyAuthcodeExchangeTokenResponseForOpenIDAndOfflineAccess(
+					happyLDAPCustomSessionData,
+				),
+			},
+			refreshRequest: refreshRequestInputs{
+				want: tokenEndpointResponseExpectedValues{
+					wantStatus: http.StatusUnauthorized,
+					wantErrorResponseBody: here.Doc(`
+						{
+							"error":             "error",
+							"error_description": "Error during upstream refresh. Provider from upstream session data has changed its resource UID since authentication."
+						}
+					`),
+				},
+			},
+		},
+		{
+			name: "when the active directory provider in the session storage is found but has the wrong resource UID during the refresh request",
+			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithActiveDirectory(&oidctestutil.TestUpstreamLDAPIdentityProvider{
+				Name:        activeDirectoryUpstreamName,
+				ResourceUID: "the-wrong-uid",
+				URL:         ldapUpstreamURL,
+			}),
+			authcodeExchange: authcodeExchangeInputs{
+				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },
+				customSessionData: happyActiveDirectoryCustomSessionData,
+				want: happyAuthcodeExchangeTokenResponseForOpenIDAndOfflineAccess(
+					happyActiveDirectoryCustomSessionData,
+				),
+			},
+			refreshRequest: refreshRequestInputs{
+				want: tokenEndpointResponseExpectedValues{
+					wantStatus: http.StatusUnauthorized,
+					wantErrorResponseBody: here.Doc(`
+						{
+							"error":             "error",
+							"error_description": "Error during upstream refresh. Provider from upstream session data has changed its resource UID since authentication."
+						}
+					`),
+				},
+			},
+		},
 	}
 	for _, test := range tests {
 		test := test

internal/psession/pinniped_session.go

@@ -67,11 +67,13 @@ type OIDCSessionData struct {
 // LDAPSessionData is the additional data needed by Pinniped when the upstream IDP is an LDAP provider.
 type LDAPSessionData struct {
 	UserDN                 string            `json:"userDN"`
+	ExtraRefreshAttributes map[string]string `json:"extraRefreshAttributes,omitempty"`
 }
 
 // ActiveDirectorySessionData is the additional data needed by Pinniped when the upstream IDP is an Active Directory provider.
 type ActiveDirectorySessionData struct {
 	UserDN                 string            `json:"userDN"`
+	ExtraRefreshAttributes map[string]string `json:"extraRefreshAttributes,omitempty"`
 }
 
 // NewPinnipedSession returns a new empty session.

internal/testutil/oidctestutil/oidctestutil.go

@@ -111,16 +111,16 @@ func (u *TestUpstreamLDAPIdentityProvider) GetURL() *url.URL {
 	return u.URL
 }
 
-func (u *TestUpstreamLDAPIdentityProvider) PerformRefresh(ctx context.Context, userDN, expectedUsername, expectedSubject string) error {
+func (u *TestUpstreamLDAPIdentityProvider) PerformRefresh(ctx context.Context, storedRefreshAttributes provider.StoredRefreshAttributes) error {
 	if u.performRefreshArgs == nil {
 		u.performRefreshArgs = make([]*PerformRefreshArgs, 0)
 	}
 	u.performRefreshCallCount++
 	u.performRefreshArgs = append(u.performRefreshArgs, &PerformRefreshArgs{
 		Ctx:              ctx,
-		DN:               userDN,
+		DN:               storedRefreshAttributes.DN,
-		ExpectedUsername: expectedUsername,
+		ExpectedUsername: storedRefreshAttributes.Username,
-		ExpectedSubject:  expectedSubject,
+		ExpectedSubject:  storedRefreshAttributes.Subject,
 	})
 	if u.PerformRefreshErr != nil {
 		return u.PerformRefreshErr

internal/upstreamldap/upstreamldap.go

@@ -13,13 +13,11 @@ import (
 	"fmt"
 	"net"
 	"net/url"
-	"regexp"
 	"sort"
 	"strings"
 	"time"
 
 	"github.com/go-ldap/ldap/v3"
-	"github.com/google/uuid"
 	"k8s.io/apimachinery/pkg/types"
 	"k8s.io/apiserver/pkg/authentication/user"
 	"k8s.io/utils/trace"
@@ -39,7 +37,6 @@ const (
 	groupSearchPageSize                     = uint32(250)
 	defaultLDAPPort                         = uint16(389)
 	defaultLDAPSPort                        = uint16(636)
-	sAMAccountNameAttribute                 = "sAMAccountName"
 )
 
 // Conn abstracts the upstream LDAP communication protocol (mostly for testing).
@@ -119,6 +116,9 @@ type ProviderConfig struct {
 	// GroupNameMappingOverrides are the mappings between an attribute name and a way to parse it as a group
 	// name when it comes out of LDAP.
 	GroupAttributeParsingOverrides map[string]func(*ldap.Entry) (string, error)
+
+	// RefreshAttributeChecks are extra checks that attributes in a refresh response are as expected.
+	RefreshAttributeChecks map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error
 }
 
 // UserSearchConfig contains information about how to search for users in the upstream LDAP IDP.
@@ -170,9 +170,11 @@ func (p *Provider) GetConfig() ProviderConfig {
 	return p.c
 }
 
-func (p *Provider) PerformRefresh(ctx context.Context, userDN, expectedUsername, expectedSubject string) error {
+func (p *Provider) PerformRefresh(ctx context.Context, storedRefreshAttributes provider.StoredRefreshAttributes) error {
 	t := trace.FromContext(ctx).Nest("slow ldap refresh attempt", trace.Field{Key: "providerName", Value: p.GetName()})
 	defer t.LogIfLong(500 * time.Millisecond) // to help users debug slow LDAP searches
+	userDN := storedRefreshAttributes.DN
+
 	searchResult, err := p.performRefresh(ctx, userDN)
 	if err != nil {
 		p.traceRefreshFailure(t, err)
@@ -196,9 +198,9 @@ func (p *Provider) PerformRefresh(ctx context.Context, userDN, expectedUsername,
 	if err != nil {
 		return err
 	}
-	if newUsername != expectedUsername {
+	if newUsername != storedRefreshAttributes.Username {
 		return fmt.Errorf(`searching for user "%s" returned a different username than the previous value. expected: "%s", actual: "%s"`,
-			userDN, expectedUsername, newUsername,
+			userDN, storedRefreshAttributes.Username, newUsername,
 		)
 	}
 
@@ -207,10 +209,15 @@ func (p *Provider) PerformRefresh(ctx context.Context, userDN, expectedUsername,
 		return err
 	}
 	newSubject := downstreamsession.DownstreamLDAPSubject(newUID, *p.GetURL())
-	if newSubject != expectedSubject {
+	if newSubject != storedRefreshAttributes.Subject {
-		return fmt.Errorf(`searching for user "%s" produced a different subject than the previous value. expected: "%s", actual: "%s"`, userDN, expectedSubject, newSubject)
+		return fmt.Errorf(`searching for user "%s" produced a different subject than the previous value. expected: "%s", actual: "%s"`, userDN, storedRefreshAttributes.Subject, newSubject)
+	}
+	for attribute, validateFunc := range p.c.RefreshAttributeChecks {
+		err = validateFunc(userEntry, storedRefreshAttributes)
+		if err != nil {
+			return fmt.Errorf(`validation for attribute "%s" failed during upstream refresh: %w`, attribute, err)
+		}
 	}
-
 	// we checked that the user still exists and their information is the same, so just return.
 	return nil
 }
@@ -569,6 +576,15 @@ func (p *Provider) searchAndBindUser(conn Conn, username string, bindFunc func(c
 	}
 	sort.Strings(mappedGroupNames)
 
+	mappedRefreshAttributes := make(map[string]string)
+	for k := range p.c.RefreshAttributeChecks {
+		mappedVal, err := p.getSearchResultAttributeRawValueEncoded(k, userEntry, username)
+		if err != nil {
+			return nil, err
+		}
+		mappedRefreshAttributes[k] = mappedVal
+	}
+
 	// Caution: Note that any other LDAP commands after this bind will be run as this user instead of as the configured BindUsername!
 	err = bindFunc(conn, userEntry.DN)
 	if err != nil {
@@ -593,6 +609,7 @@ func (p *Provider) searchAndBindUser(conn Conn, username string, bindFunc func(c
 			Groups: mappedGroupNames,
 		},
 		DN:                     userEntry.DN,
+		ExtraRefreshAttributes: mappedRefreshAttributes,
 	}
 
 	return response, nil
@@ -665,6 +682,9 @@ func (p *Provider) userSearchRequestedAttributes() []string {
 	if p.c.UserSearch.UIDAttribute != distinguishedNameAttributeName {
 		attributes = append(attributes, p.c.UserSearch.UIDAttribute)
 	}
+	for k := range p.c.RefreshAttributeChecks {
+		attributes = append(attributes, k)
+	}
 	return attributes
 }
 
@@ -782,57 +802,18 @@ func (p *Provider) traceRefreshFailure(t *trace.Trace, err error) {
 	)
 }
 
-func MicrosoftUUIDFromBinary(attributeName string) func(entry *ldap.Entry) (string, error) {
+func AttributeUnchangedSinceLogin(attribute string) func(*ldap.Entry, provider.StoredRefreshAttributes) error {
-	// validation has already been done so we can just get the attribute...
+	return func(entry *ldap.Entry, storedAttributes provider.StoredRefreshAttributes) error {
-	return func(entry *ldap.Entry) (string, error) {
+		prevAttributeValue := storedAttributes.AdditionalAttributes[attribute]
-		binaryUUID := entry.GetRawAttributeValue(attributeName)
+		newValues := entry.GetAttributeValues(attribute)
-		return microsoftUUIDFromBinary(binaryUUID)
+
+		if len(newValues) != 1 {
+			return fmt.Errorf(`expected to find 1 value for "%s" attribute, but found %d`, attribute, len(newValues))
+		}
+		encodedNewValue := base64.RawURLEncoding.EncodeToString(entry.GetRawAttributeValue(attribute))
+		if prevAttributeValue != encodedNewValue {
+			return fmt.Errorf(`value for attribute "%s" has changed since initial value at login`, attribute)
+		}
+		return nil
 	}
 }
-
-func microsoftUUIDFromBinary(binaryUUID []byte) (string, error) {
-	uuidVal, err := uuid.FromBytes(binaryUUID) // start out with the RFC4122 version
-	if err != nil {
-		return "", err
-	}
-	// then swap it because AD stores the first 3 fields little-endian rather than the expected
-	// big-endian.
-	uuidVal[0], uuidVal[1], uuidVal[2], uuidVal[3] = uuidVal[3], uuidVal[2], uuidVal[1], uuidVal[0]
-	uuidVal[4], uuidVal[5] = uuidVal[5], uuidVal[4]
-	uuidVal[6], uuidVal[7] = uuidVal[7], uuidVal[6]
-	return uuidVal.String(), nil
-}
-
-func GroupSAMAccountNameWithDomainSuffix(entry *ldap.Entry) (string, error) {
-	sAMAccountNameAttributeValues := entry.GetAttributeValues(sAMAccountNameAttribute)
-
-	if len(sAMAccountNameAttributeValues) != 1 {
-		return "", fmt.Errorf(`found %d values for attribute "%s", but expected 1 result`,
-			len(sAMAccountNameAttributeValues), sAMAccountNameAttribute,
-		)
-	}
-
-	sAMAccountName := sAMAccountNameAttributeValues[0]
-	if len(sAMAccountName) == 0 {
-		return "", fmt.Errorf(`found empty value for attribute "%s", but expected value to be non-empty`,
-			sAMAccountNameAttribute,
-		)
-	}
-
-	distinguishedName := entry.DN
-	domain, err := getDomainFromDistinguishedName(distinguishedName)
-	if err != nil {
-		return "", err
-	}
-	return sAMAccountName + "@" + domain, nil
-}
-
-var domainComponentsRegexp = regexp.MustCompile(",DC=|,dc=")
-
-func getDomainFromDistinguishedName(distinguishedName string) (string, error) {
-	domainComponents := domainComponentsRegexp.Split(distinguishedName, -1)
-	if len(domainComponents) == 1 {
-		return "", fmt.Errorf("did not find domain components in group dn: %s", distinguishedName)
-	}
-	return strings.Join(domainComponents[1:], "."), nil
-}

internal/upstreamldap/upstreamldap_test.go

@@ -26,6 +26,7 @@ import (
 	"go.pinniped.dev/internal/crypto/ptls"
 	"go.pinniped.dev/internal/endpointaddr"
 	"go.pinniped.dev/internal/mocks/mockldapconn"
+	"go.pinniped.dev/internal/oidc/provider"
 	"go.pinniped.dev/internal/testutil"
 	"go.pinniped.dev/internal/testutil/tlsserver"
 )
@@ -154,16 +155,17 @@ func TestEndUserAuthentication(t *testing.T) {
 	}
 
 	// The auth response which matches the exampleUserSearchResult and exampleGroupSearchResult.
-	expectedAuthResponse := func(editFunc func(r *user.DefaultInfo)) *authenticators.Response {
+	expectedAuthResponse := func(editFunc func(r *authenticators.Response)) *authenticators.Response {
 		u := &user.DefaultInfo{
 			Name:   testUserSearchResultUsernameAttributeValue,
 			UID:    base64.RawURLEncoding.EncodeToString([]byte(testUserSearchResultUIDAttributeValue)),
 			Groups: []string{testGroupSearchResultGroupNameAttributeValue1, testGroupSearchResultGroupNameAttributeValue2},
 		}
+		response := &authenticators.Response{User: u, DN: testUserSearchResultDNValue, ExtraRefreshAttributes: map[string]string{}}
 		if editFunc != nil {
-			editFunc(u)
+			editFunc(response)
 		}
-		return &authenticators.Response{User: u, DN: testUserSearchResultDNValue}
+		return response
 	}
 
 	tests := []struct {
@@ -250,8 +252,9 @@ func TestEndUserAuthentication(t *testing.T) {
 			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
 				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
 			},
-			wantAuthResponse: expectedAuthResponse(func(r *user.DefaultInfo) {
+			wantAuthResponse: expectedAuthResponse(func(r *authenticators.Response) {
-				r.Groups = []string{}
+				info := r.User.(*user.DefaultInfo)
+				info.Groups = []string{}
 			}),
 		},
 		{
@@ -282,8 +285,9 @@ func TestEndUserAuthentication(t *testing.T) {
 			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
 				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
 			},
-			wantAuthResponse: expectedAuthResponse(func(r *user.DefaultInfo) {
+			wantAuthResponse: expectedAuthResponse(func(r *authenticators.Response) {
-				r.Name = testUserSearchResultDNValue
+				info := r.User.(*user.DefaultInfo)
+				info.Name = testUserSearchResultDNValue
 			}),
 		},
 		{
@@ -314,8 +318,9 @@ func TestEndUserAuthentication(t *testing.T) {
 			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
 				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
 			},
-			wantAuthResponse: expectedAuthResponse(func(r *user.DefaultInfo) {
+			wantAuthResponse: expectedAuthResponse(func(r *authenticators.Response) {
-				r.UID = base64.RawURLEncoding.EncodeToString([]byte(testUserSearchResultDNValue))
+				info := r.User.(*user.DefaultInfo)
+				info.UID = base64.RawURLEncoding.EncodeToString([]byte(testUserSearchResultDNValue))
 			}),
 		},
 		{
@@ -337,8 +342,9 @@ func TestEndUserAuthentication(t *testing.T) {
 			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
 				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
 			},
-			wantAuthResponse: expectedAuthResponse(func(r *user.DefaultInfo) {
+			wantAuthResponse: expectedAuthResponse(func(r *authenticators.Response) {
-				r.Groups = []string{testGroupSearchResultDNValue1, testGroupSearchResultDNValue2}
+				info := r.User.(*user.DefaultInfo)
+				info.Groups = []string{testGroupSearchResultDNValue1, testGroupSearchResultDNValue2}
 			}),
 		},
 		{
@@ -360,8 +366,9 @@ func TestEndUserAuthentication(t *testing.T) {
 			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
 				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
 			},
-			wantAuthResponse: expectedAuthResponse(func(r *user.DefaultInfo) {
+			wantAuthResponse: expectedAuthResponse(func(r *authenticators.Response) {
-				r.Groups = []string{testGroupSearchResultDNValue1, testGroupSearchResultDNValue2}
+				info := r.User.(*user.DefaultInfo)
+				info.Groups = []string{testGroupSearchResultDNValue1, testGroupSearchResultDNValue2}
 			}),
 		},
 		{
@@ -508,32 +515,36 @@ func TestEndUserAuthentication(t *testing.T) {
 					Groups: []string{"a", "b", "c"},
 				},
 				DN:                     testUserSearchResultDNValue,
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
-			name:     "override UID parsing to work with microsoft style objectGUIDs",
+			name:     "requesting additional refresh related attributes",
 			username: testUpstreamUsername,
 			password: testUpstreamPassword,
 			providerConfig: providerConfig(func(p *ProviderConfig) {
-				p.UIDAttributeParsingOverrides = map[string]func(entry *ldap.Entry) (string, error){
+				p.RefreshAttributeChecks = map[string]func(entry *ldap.Entry, attributes provider.StoredRefreshAttributes) error{
-					"objectGUID": MicrosoftUUIDFromBinary("objectGUID"),
+					"some-attribute-to-check-during-refresh": func(entry *ldap.Entry, attributes provider.StoredRefreshAttributes) error {
+						return nil
+					},
 				}
-				p.UserSearch.UIDAttribute = "objectGUID"
 			}),
 			searchMocks: func(conn *mockldapconn.MockConn) {
 				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
 				conn.EXPECT().Search(expectedUserSearch(func(r *ldap.SearchRequest) {
-					r.Attributes = []string{testUserSearchUsernameAttribute, "objectGUID"}
+					r.Attributes = append(r.Attributes, "some-attribute-to-check-during-refresh")
 				})).Return(&ldap.SearchResult{
 					Entries: []*ldap.Entry{
 						{
 							DN: testUserSearchResultDNValue,
 							Attributes: []*ldap.EntryAttribute{
 								ldap.NewEntryAttribute(testUserSearchUsernameAttribute, []string{testUserSearchResultUsernameAttributeValue}),
-								ldap.NewEntryAttribute("objectGUID", []string{"\x01\x02\x03\x04\x05\x06\x07\x08\x09\x10\x11\x12\x13\x14\x15\x16"}),
+								ldap.NewEntryAttribute(testUserSearchUIDAttribute, []string{testUserSearchResultUIDAttributeValue}),
+								ldap.NewEntryAttribute("some-attribute-to-check-during-refresh", []string{"some-attribute-value"}),
 							},
 						},
-					}}, nil).Times(1)
+					},
+				}, nil).Times(1)
 				conn.EXPECT().SearchWithPaging(expectedGroupSearch(nil), expectedGroupSearchPageSize).
 					Return(exampleGroupSearchResult, nil).Times(1)
 				conn.EXPECT().Close().Times(1)
@@ -541,172 +552,31 @@ func TestEndUserAuthentication(t *testing.T) {
 			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
 				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
 			},
-			wantAuthResponse: expectedAuthResponse(func(r *user.DefaultInfo) {
+			wantAuthResponse: expectedAuthResponse(func(r *authenticators.Response) {
-				r.UID = "04030201-0605-0807-0910-111213141516"
+				r.ExtraRefreshAttributes = map[string]string{"some-attribute-to-check-during-refresh": "c29tZS1hdHRyaWJ1dGUtdmFsdWU"}
 			}),
 		},
 		{
-			name:     "override UID parsing when the attribute name doesn't match what's returned does default parsing",
+			name:     "requesting additional refresh related attributes, but they aren't returned",
 			username: testUpstreamUsername,
 			password: testUpstreamPassword,
 			providerConfig: providerConfig(func(p *ProviderConfig) {
-				p.UIDAttributeParsingOverrides = map[string]func(entry *ldap.Entry) (string, error){
+				p.RefreshAttributeChecks = map[string]func(entry *ldap.Entry, attributes provider.StoredRefreshAttributes) error{
-					"objectGUID": MicrosoftUUIDFromBinary("objectGUID"),
+					"some-attribute-to-check-during-refresh": func(entry *ldap.Entry, attributes provider.StoredRefreshAttributes) error {
+						return nil
+					},
 				}
 			}),
 			searchMocks: func(conn *mockldapconn.MockConn) {
 				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
-				conn.EXPECT().Search(expectedUserSearch(nil)).Return(exampleUserSearchResult, nil).Times(1)
+				conn.EXPECT().Search(expectedUserSearch(func(r *ldap.SearchRequest) {
+					r.Attributes = append(r.Attributes, "some-attribute-to-check-during-refresh")
+				})).Return(exampleUserSearchResult, nil).Times(1)
 				conn.EXPECT().SearchWithPaging(expectedGroupSearch(nil), expectedGroupSearchPageSize).
 					Return(exampleGroupSearchResult, nil).Times(1)
 				conn.EXPECT().Close().Times(1)
 			},
-			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
+			wantError: "found 0 values for attribute \"some-attribute-to-check-during-refresh\" while searching for user \"some-upstream-username\", but expected 1 result",
-				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
-			},
-			wantAuthResponse: expectedAuthResponse(nil),
-		},
-		{
-			name:     "override group parsing to create new group names",
-			username: testUpstreamUsername,
-			password: testUpstreamPassword,
-			providerConfig: providerConfig(func(p *ProviderConfig) {
-				p.GroupSearch.GroupNameAttribute = "sAMAccountName"
-				p.GroupAttributeParsingOverrides = map[string]func(*ldap.Entry) (string, error){
-					"sAMAccountName": GroupSAMAccountNameWithDomainSuffix,
-				}
-			}),
-			searchMocks: func(conn *mockldapconn.MockConn) {
-				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
-				conn.EXPECT().Search(expectedUserSearch(nil)).Return(exampleUserSearchResult, nil).Times(1)
-				conn.EXPECT().SearchWithPaging(expectedGroupSearch(func(r *ldap.SearchRequest) {
-					r.Attributes = []string{"sAMAccountName"}
-				}), expectedGroupSearchPageSize).
-					Return(&ldap.SearchResult{
-						Entries: []*ldap.Entry{
-							{
-								DN: "CN=Mammals,OU=Users,OU=pinniped-ad,DC=activedirectory,DC=mycompany,DC=example,DC=com",
-								Attributes: []*ldap.EntryAttribute{
-									ldap.NewEntryAttribute("sAMAccountName", []string{"Mammals"}),
-								},
-							},
-							{
-								DN: "CN=Animals,OU=Users,OU=pinniped-ad,DC=activedirectory,DC=mycompany,DC=example,DC=com",
-								Attributes: []*ldap.EntryAttribute{
-									ldap.NewEntryAttribute("sAMAccountName", []string{"Animals"}),
-								},
-							},
-						},
-						Referrals: []string{}, // note that we are not following referrals at this time
-						Controls:  []ldap.Control{},
-					}, nil).Times(1)
-				conn.EXPECT().Close().Times(1)
-			},
-			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
-				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
-			},
-			wantAuthResponse: expectedAuthResponse(func(r *user.DefaultInfo) {
-				r.Groups = []string{"Animals@activedirectory.mycompany.example.com", "Mammals@activedirectory.mycompany.example.com"}
-			}),
-		},
-		{
-			name:     "override group parsing when domain can't be determined from dn",
-			username: testUpstreamUsername,
-			password: testUpstreamPassword,
-			providerConfig: providerConfig(func(p *ProviderConfig) {
-				p.GroupSearch.GroupNameAttribute = "sAMAccountName"
-				p.GroupAttributeParsingOverrides = map[string]func(*ldap.Entry) (string, error){
-					"sAMAccountName": GroupSAMAccountNameWithDomainSuffix,
-				}
-			}),
-			searchMocks: func(conn *mockldapconn.MockConn) {
-				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
-				conn.EXPECT().Search(expectedUserSearch(nil)).Return(exampleUserSearchResult, nil).Times(1)
-				conn.EXPECT().SearchWithPaging(expectedGroupSearch(func(r *ldap.SearchRequest) {
-					r.Attributes = []string{"sAMAccountName"}
-				}), expectedGroupSearchPageSize).
-					Return(&ldap.SearchResult{
-						Entries: []*ldap.Entry{
-							{
-								DN: "no-domain-components",
-								Attributes: []*ldap.EntryAttribute{
-									ldap.NewEntryAttribute("sAMAccountName", []string{"Mammals"}),
-								},
-							},
-							{
-								DN: "CN=Animals,OU=Users,OU=pinniped-ad,DC=activedirectory,DC=mycompany,DC=example,DC=com",
-								Attributes: []*ldap.EntryAttribute{
-									ldap.NewEntryAttribute("sAMAccountName", []string{"Animals"}),
-								},
-							},
-						},
-						Referrals: []string{}, // note that we are not following referrals at this time
-						Controls:  []ldap.Control{},
-					}, nil).Times(1)
-				conn.EXPECT().Close().Times(1)
-			},
-			wantError: "error finding groups for user some-upstream-user-dn: did not find domain components in group dn: no-domain-components",
-		},
-		{
-			name:     "override group parsing when entry has multiple values for attribute",
-			username: testUpstreamUsername,
-			password: testUpstreamPassword,
-			providerConfig: providerConfig(func(p *ProviderConfig) {
-				p.GroupSearch.GroupNameAttribute = "sAMAccountName"
-				p.GroupAttributeParsingOverrides = map[string]func(*ldap.Entry) (string, error){
-					"sAMAccountName": GroupSAMAccountNameWithDomainSuffix,
-				}
-			}),
-			searchMocks: func(conn *mockldapconn.MockConn) {
-				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
-				conn.EXPECT().Search(expectedUserSearch(nil)).Return(exampleUserSearchResult, nil).Times(1)
-				conn.EXPECT().SearchWithPaging(expectedGroupSearch(func(r *ldap.SearchRequest) {
-					r.Attributes = []string{"sAMAccountName"}
-				}), expectedGroupSearchPageSize).
-					Return(&ldap.SearchResult{
-						Entries: []*ldap.Entry{
-							{
-								DN: "no-domain-components",
-								Attributes: []*ldap.EntryAttribute{
-									ldap.NewEntryAttribute("sAMAccountName", []string{"Mammals", "Eukaryotes"}),
-								},
-							},
-						},
-						Referrals: []string{}, // note that we are not following referrals at this time
-						Controls:  []ldap.Control{},
-					}, nil).Times(1)
-				conn.EXPECT().Close().Times(1)
-			},
-			wantError: "error finding groups for user some-upstream-user-dn: found 2 values for attribute \"sAMAccountName\", but expected 1 result",
-		}, {
-			name:     "override group parsing when entry has no values for attribute",
-			username: testUpstreamUsername,
-			password: testUpstreamPassword,
-			providerConfig: providerConfig(func(p *ProviderConfig) {
-				p.GroupSearch.GroupNameAttribute = "sAMAccountName"
-				p.GroupAttributeParsingOverrides = map[string]func(*ldap.Entry) (string, error){
-					"sAMAccountName": GroupSAMAccountNameWithDomainSuffix,
-				}
-			}),
-			searchMocks: func(conn *mockldapconn.MockConn) {
-				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
-				conn.EXPECT().Search(expectedUserSearch(nil)).Return(exampleUserSearchResult, nil).Times(1)
-				conn.EXPECT().SearchWithPaging(expectedGroupSearch(func(r *ldap.SearchRequest) {
-					r.Attributes = []string{"sAMAccountName"}
-				}), expectedGroupSearchPageSize).
-					Return(&ldap.SearchResult{
-						Entries: []*ldap.Entry{
-							{
-								DN:         "no-domain-components",
-								Attributes: []*ldap.EntryAttribute{},
-							},
-						},
-						Referrals: []string{}, // note that we are not following referrals at this time
-						Controls:  []ldap.Control{},
-					}, nil).Times(1)
-				conn.EXPECT().Close().Times(1)
-			},
-			wantError: "error finding groups for user some-upstream-user-dn: found 0 values for attribute \"sAMAccountName\", but expected 1 result",
 		},
 		{
 			name:           "when dial fails",
@@ -1162,9 +1032,9 @@ func TestEndUserAuthentication(t *testing.T) {
 				return conn, nil
 			})
 
-			provider := New(*tt.providerConfig)
+			ldapProvider := New(*tt.providerConfig)
 
-			authResponse, authenticated, err := provider.AuthenticateUser(context.Background(), tt.username, tt.password)
+			authResponse, authenticated, err := ldapProvider.AuthenticateUser(context.Background(), tt.username, tt.password)
 			require.Equal(t, !tt.wantToSkipDial, dialWasAttempted)
 			switch {
 			case tt.wantError != "":
@@ -1196,7 +1066,7 @@ func TestEndUserAuthentication(t *testing.T) {
 			}
 			// Skip tt.bindEndUserMocks since DryRunAuthenticateUser() never binds as the end user.
 
-			authResponse, authenticated, err = provider.DryRunAuthenticateUser(context.Background(), tt.username)
+			authResponse, authenticated, err = ldapProvider.DryRunAuthenticateUser(context.Background(), tt.username)
 			require.Equal(t, !tt.wantToSkipDial, dialWasAttempted)
 			switch {
 			case tt.wantError != "":
@@ -1217,6 +1087,7 @@ func TestEndUserAuthentication(t *testing.T) {
 }
 
 func TestUpstreamRefresh(t *testing.T) {
+	pwdLastSetAttribute := "pwdLastSet"
 	expectedUserSearch := &ldap.SearchRequest{
 		BaseDN:       testUserSearchResultDNValue,
 		Scope:        ldap.ScopeBaseObject,
@@ -1225,7 +1096,7 @@ func TestUpstreamRefresh(t *testing.T) {
 		TimeLimit:    90,
 		TypesOnly:    false,
 		Filter:       "(objectClass=*)",
-		Attributes:   []string{testUserSearchUsernameAttribute, testUserSearchUIDAttribute},
+		Attributes:   []string{testUserSearchUsernameAttribute, testUserSearchUIDAttribute, pwdLastSetAttribute},
 		Controls:     nil, // don't need paging because we set the SizeLimit so small
 	}
 
@@ -1242,6 +1113,11 @@ func TestUpstreamRefresh(t *testing.T) {
 						Name:       testUserSearchUIDAttribute,
 						ByteValues: [][]byte{[]byte(testUserSearchResultUIDAttributeValue)},
 					},
+					{
+						Name:       pwdLastSetAttribute,
+						Values:     []string{"132801740800000000"},
+						ByteValues: [][]byte{[]byte("132801740800000000")},
+					},
 				},
 			},
 		},
@@ -1259,6 +1135,9 @@ func TestUpstreamRefresh(t *testing.T) {
 			UIDAttribute:      testUserSearchUIDAttribute,
 			UsernameAttribute: testUserSearchUsernameAttribute,
 		},
+		RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+			pwdLastSetAttribute: AttributeUnchangedSinceLogin(pwdLastSetAttribute),
+		},
 	}
 
 	tests := []struct {
@@ -1512,6 +1391,36 @@ func TestUpstreamRefresh(t *testing.T) {
 			},
 			wantErr: "found 2 values for attribute \"some-upstream-uid-attribute\" while searching for user \"some-upstream-user-dn\", but expected 1 result",
 		},
+		{
+			name:           "search result has a changed pwdLastSet value",
+			providerConfig: providerConfig,
+			setupMocks: func(conn *mockldapconn.MockConn) {
+				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
+				conn.EXPECT().Search(expectedUserSearch).Return(&ldap.SearchResult{
+					Entries: []*ldap.Entry{
+						{
+							DN: testUserSearchResultDNValue,
+							Attributes: []*ldap.EntryAttribute{
+								{
+									Name:   testUserSearchUsernameAttribute,
+									Values: []string{testUserSearchResultUsernameAttributeValue},
+								},
+								{
+									Name:       testUserSearchUIDAttribute,
+									ByteValues: [][]byte{[]byte(testUserSearchResultUIDAttributeValue)},
+								},
+								{
+									Name:   pwdLastSetAttribute,
+									Values: []string{"132801740800000001"},
+								},
+							},
+						},
+					},
+				}, nil).Times(1)
+				conn.EXPECT().Close().Times(1)
+			},
+			wantErr: "validation for attribute \"pwdLastSet\" failed during upstream refresh: value for attribute \"pwdLastSet\" has changed since initial value at login",
+		},
 	}
 
 	for _, tt := range tests {
@@ -1536,9 +1445,15 @@ func TestUpstreamRefresh(t *testing.T) {
 				return conn, nil
 			})
 
-			provider := New(*providerConfig)
+			initialPwdLastSetEncoded := base64.RawURLEncoding.EncodeToString([]byte("132801740800000000"))
+			ldapProvider := New(*providerConfig)
 			subject := "ldaps://ldap.example.com:8443?base=some-upstream-user-base-dn&sub=c29tZS11cHN0cmVhbS11aWQtdmFsdWU"
-			err := provider.PerformRefresh(context.Background(), testUserSearchResultDNValue, testUserSearchResultUsernameAttributeValue, subject)
+			err := ldapProvider.PerformRefresh(context.Background(), provider.StoredRefreshAttributes{
+				Username:             testUserSearchResultUsernameAttributeValue,
+				Subject:              subject,
+				DN:                   testUserSearchResultDNValue,
+				AdditionalAttributes: map[string]string{pwdLastSetAttribute: initialPwdLastSetEncoded},
+			})
 			if tt.wantErr != "" {
 				require.Error(t, err)
 				require.Equal(t, tt.wantErr, err.Error())
@@ -1846,73 +1761,76 @@ func TestRealTLSDialing(t *testing.T) {
 	}
 }
 
-func TestGetMicrosoftFormattedUUID(t *testing.T) {
+func TestAttributeUnchangedSinceLogin(t *testing.T) {
+	initialVal := "some-attribute-value"
+	changedVal := "some-different-attribute-value"
+	attributeName := "some-attribute-name"
 	tests := []struct {
 		name       string
-		binaryUUID []byte
+		entry      *ldap.Entry
-		wantString string
+		wantResult bool
 		wantErr    string
 	}{
 		{
-			name:       "happy path",
+			name: "happy path where value has not changed since login",
-			binaryUUID: []byte("\x01\x02\x03\x04\x05\x06\x07\x08\x09\x10\x11\x12\x13\x14\x15\x16"),
+			entry: &ldap.Entry{
-			wantString: "04030201-0605-0807-0910-111213141516",
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:       attributeName,
+						Values:     []string{initialVal},
+						ByteValues: [][]byte{[]byte(initialVal)},
+					},
+				},
+			},
 		},
 		{
-			name:       "not the right length",
+			name: "password has been reset since login",
-			binaryUUID: []byte("2\xf8\xb0\xaa\xb6V\xb1D\x8b(\xee"),
+			entry: &ldap.Entry{
-			wantErr:    "invalid UUID (got 11 bytes)",
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:       attributeName,
+						Values:     []string{changedVal},
+						ByteValues: [][]byte{[]byte(changedVal)},
+					},
+				},
+			},
+			wantErr: "value for attribute \"some-attribute-name\" has changed since initial value at login",
+		},
+		{
+			name: "no value for attribute attribute",
+			entry: &ldap.Entry{
+				DN:         "some-dn",
+				Attributes: []*ldap.EntryAttribute{},
+			},
+			wantErr: "expected to find 1 value for \"some-attribute-name\" attribute, but found 0",
+		},
+		{
+			name: "too many values for attribute",
+			entry: &ldap.Entry{
+				DN: "some-dn",
+				Attributes: []*ldap.EntryAttribute{
+					{
+						Name:   attributeName,
+						Values: []string{"val1", "val2"},
+					},
+				},
+			},
+			wantErr: "expected to find 1 value for \"some-attribute-name\" attribute, but found 2",
 		},
 	}
-
 	for _, test := range tests {
 		tt := test
 		t.Run(tt.name, func(t *testing.T) {
-			actualUUIDString, err := microsoftUUIDFromBinary(tt.binaryUUID)
+			initialValRawEncoded := base64.RawURLEncoding.EncodeToString([]byte(initialVal))
+			err := AttributeUnchangedSinceLogin(attributeName)(tt.entry, provider.StoredRefreshAttributes{AdditionalAttributes: map[string]string{attributeName: initialValRawEncoded}})
 			if tt.wantErr != "" {
-				require.EqualError(t, err, tt.wantErr)
+				require.Error(t, err)
+				require.Equal(t, tt.wantErr, err.Error())
 			} else {
 				require.NoError(t, err)
 			}
-			require.Equal(t, tt.wantString, actualUUIDString)
-		})
-	}
-}
-
-func TestGetDomainFromDistinguishedName(t *testing.T) {
-	tests := []struct {
-		name              string
-		distinguishedName string
-		wantDomain        string
-		wantErr           string
-	}{
-		{
-			name:              "happy path",
-			distinguishedName: "CN=Mammals,OU=Users,OU=pinniped-ad,DC=activedirectory,DC=mycompany,DC=example,DC=com",
-			wantDomain:        "activedirectory.mycompany.example.com",
-		},
-		{
-			name:              "lowercased happy path",
-			distinguishedName: "cn=Mammals,ou=Users,ou=pinniped-ad,dc=activedirectory,dc=mycompany,dc=example,dc=com",
-			wantDomain:        "activedirectory.mycompany.example.com",
-		},
-		{
-			name:              "no domain components",
-			distinguishedName: "not-a-dn",
-			wantErr:           "did not find domain components in group dn: not-a-dn",
-		},
-	}
-
-	for _, test := range tests {
-		tt := test
-		t.Run(tt.name, func(t *testing.T) {
-			actualDomain, err := getDomainFromDistinguishedName(tt.distinguishedName)
-			if tt.wantErr != "" {
-				require.EqualError(t, err, tt.wantErr)
-			} else {
-				require.NoError(t, err)
-			}
-			require.Equal(t, tt.wantDomain, actualDomain)
 		})
 	}
 }

test/integration/ldap_client_test.go

@@ -83,7 +83,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 			password: pinnyPassword,
 			provider: upstreamldap.New(*providerConfig(nil)),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -95,7 +97,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.ConnectionProtocol = upstreamldap.StartTLS
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -104,7 +108,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 			password: pinnyPassword,
 			provider: upstreamldap.New(*providerConfig(func(p *upstreamldap.ProviderConfig) { p.UserSearch.Base = "dc=pinniped,dc=dev" })),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -113,7 +119,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 			password: pinnyPassword,
 			provider: upstreamldap.New(*providerConfig(func(p *upstreamldap.ProviderConfig) { p.UserSearch.Filter = "(cn={})" })),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -125,7 +133,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.UserSearch.Filter = "cn={}"
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "cn=pinny,ou=users,dc=pinniped,dc=dev", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "cn=pinny,ou=users,dc=pinniped,dc=dev", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -136,7 +146,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.UserSearch.Filter = "(|(cn={})(mail={}))"
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -147,7 +159,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.UserSearch.Filter = "(|(cn={})(mail={}))"
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -156,7 +170,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 			password: pinnyPassword,
 			provider: upstreamldap.New(*providerConfig(func(p *upstreamldap.ProviderConfig) { p.UserSearch.UIDAttribute = "dn" })),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("cn=pinny,ou=users,dc=pinniped,dc=dev"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("cn=pinny,ou=users,dc=pinniped,dc=dev"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -165,7 +181,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 			password: pinnyPassword,
 			provider: upstreamldap.New(*providerConfig(func(p *upstreamldap.ProviderConfig) { p.UserSearch.UIDAttribute = "sn" })),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("Seal"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("Seal"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -174,7 +192,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 			password: pinnyPassword,
 			provider: upstreamldap.New(*providerConfig(func(p *upstreamldap.ProviderConfig) { p.UserSearch.UsernameAttribute = "sn" })),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "Seal", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev", // note that the final answer has case preserved from the entry
+				User:                   &user.DefaultInfo{Name: "Seal", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev", // note that the final answer has case preserved from the entry
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -187,7 +207,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.UserSearch.UIDAttribute = "givenName"
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "Pinny the 🦭", UID: b64("Pinny the 🦭"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "Pinny the 🦭", UID: b64("Pinny the 🦭"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -199,7 +221,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.UserSearch.UsernameAttribute = "cn"
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -220,7 +244,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.GroupSearch.Base = ""
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -231,7 +257,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.GroupSearch.Base = "ou=users,dc=pinniped,dc=dev" // there are no groups under this part of the tree
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -245,7 +273,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{
 					"cn=ball-game-players,ou=beach-groups,ou=groups,dc=pinniped,dc=dev",
 					"cn=seals,ou=groups,dc=pinniped,dc=dev",
-				}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -259,7 +289,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{
 					"cn=ball-game-players,ou=beach-groups,ou=groups,dc=pinniped,dc=dev",
 					"cn=seals,ou=groups,dc=pinniped,dc=dev",
-				}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -270,7 +302,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.GroupSearch.GroupNameAttribute = "objectClass" // silly example, but still a meaningful test
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"groupOfNames", "groupOfNames"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"groupOfNames", "groupOfNames"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -281,7 +315,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.GroupSearch.Filter = "(&(&(objectClass=groupOfNames)(member={}))(cn=seals))"
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"seals"}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"seals"}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -292,7 +328,9 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.GroupSearch.Filter = "foobar={}" // foobar is not a valid attribute name for this LDAP server's schema
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User: &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}}, DN: "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}},
+				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+				ExtraRefreshAttributes: map[string]string{},
 			},
 		},
 		{
@@ -673,6 +711,7 @@ func TestSimultaneousLDAPRequestsOnSingleProvider(t *testing.T) {
 		assert.Equal(t, &authenticators.Response{
 			User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"ball-game-players", "seals"}},
 			DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
+			ExtraRefreshAttributes: map[string]string{},
 		}, result.response)
 	}
 }

test/integration/supervisor_login_test.go

@@ -5,11 +5,16 @@ package integration
 
 import (
 	"context"
+	"crypto/rand"
 	"crypto/tls"
+	"crypto/x509"
 	"encoding/base64"
+	"encoding/hex"
 	"encoding/json"
 	"fmt"
 	"io/ioutil"
+	"math/big"
+	"net"
 	"net/http"
 	"net/http/httptest"
 	"net/url"
@@ -19,15 +24,18 @@ import (
 	"time"
 
 	coreosoidc "github.com/coreos/go-oidc/v3/oidc"
+	"github.com/go-ldap/ldap/v3"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"golang.org/x/oauth2"
+	"golang.org/x/text/encoding/unicode"
 	v1 "k8s.io/api/core/v1"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 
 	configv1alpha1 "go.pinniped.dev/generated/latest/apis/supervisor/config/v1alpha1"
 	idpv1alpha1 "go.pinniped.dev/generated/latest/apis/supervisor/idp/v1alpha1"
 	"go.pinniped.dev/internal/certauthority"
+	"go.pinniped.dev/internal/crypto/ptls"
 	"go.pinniped.dev/internal/oidc"
 	"go.pinniped.dev/internal/psession"
 	"go.pinniped.dev/internal/testutil"
@@ -38,24 +46,26 @@ import (
 	"go.pinniped.dev/test/testlib/browsertest"
 )
 
+// nolint:gocyclo
 func TestSupervisorLogin(t *testing.T) {
 	env := testlib.IntegrationEnv(t)
 
 	tests := []struct {
 		name                                 string
 		maybeSkip                            func(t *testing.T)
+		createTestUser                       func(t *testing.T) (string, string)
+		deleteTestUser                       func(t *testing.T, username string)
+		requestAuthorization                 func(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL, username, password string, httpClient *http.Client)
 		createIDP                            func(t *testing.T) string
-		requestAuthorization                 func(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL string, httpClient *http.Client)
 		wantDownstreamIDTokenSubjectToMatch  string
-		wantDownstreamIDTokenUsernameToMatch string
+		wantDownstreamIDTokenUsernameToMatch func(username string) string
 		wantDownstreamIDTokenGroups          []string
 		wantErrorDescription                 string
 		wantErrorType                        string
 
-		// We don't necessarily have any way to revoke the user's session on the upstream provider,
+		// Either revoke the user's session on the upstream provider, or manipulate the user's session
-		// so to cause the upstream refresh to fail we can cheat by manipulating the user's session
 		// data in such a way that it should cause the next upstream refresh attempt to fail.
-		breakRefreshSessionData func(t *testing.T, sessionData *psession.PinnipedSession, idpName string)
+		breakRefreshSessionData func(t *testing.T, sessionData *psession.PinnipedSession, idpName, username string)
 	}{
 		{
 			name: "oidc with default username and groups claim settings",
@@ -76,7 +86,7 @@ func TestSupervisorLogin(t *testing.T) {
 				return oidcIDP.Name
 			},
 			requestAuthorization: requestAuthorizationUsingBrowserAuthcodeFlow,
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeOIDC, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.OIDC.UpstreamRefreshToken)
@@ -85,7 +95,7 @@ func TestSupervisorLogin(t *testing.T) {
 			// the ID token Subject should include the upstream user ID after the upstream issuer name
 			wantDownstreamIDTokenSubjectToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Issuer+"?sub=") + ".+",
 			// the ID token Username should include the upstream user ID after the upstream issuer name
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Issuer+"?sub=") + ".+",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string { return "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Issuer+"?sub=") + ".+" },
 		},
 		{
 			name: "oidc with custom username and groups claim settings",
@@ -113,14 +123,14 @@ func TestSupervisorLogin(t *testing.T) {
 				return oidcIDP.Name
 			},
 			requestAuthorization: requestAuthorizationUsingBrowserAuthcodeFlow,
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeOIDC, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.OIDC.UpstreamRefreshToken)
 				customSessionData.OIDC.UpstreamRefreshToken = "invalid-updated-refresh-token"
 			},
 			wantDownstreamIDTokenSubjectToMatch:  "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Issuer+"?sub=") + ".+",
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Username) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string { return "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Username) + "$" },
 			wantDownstreamIDTokenGroups:          env.SupervisorUpstreamOIDC.ExpectedGroups,
 		},
 		{
@@ -144,7 +154,7 @@ func TestSupervisorLogin(t *testing.T) {
 				}, idpv1alpha1.PhaseReady)
 				return oidcIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamOIDC.Username, // username to present to server during login
@@ -153,7 +163,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeOIDC, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.OIDC.UpstreamRefreshToken)
@@ -162,7 +172,7 @@ func TestSupervisorLogin(t *testing.T) {
 			// the ID token Subject should include the upstream user ID after the upstream issuer name
 			wantDownstreamIDTokenSubjectToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Issuer+"?sub=") + ".+",
 			// the ID token Username should include the upstream user ID after the upstream issuer name
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Issuer+"?sub=") + ".+",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string { return "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Issuer+"?sub=") + ".+" },
 		},
 		{
 			name: "ldap with email as username and groups names as DNs and using an LDAP provider which supports TLS",
@@ -212,7 +222,7 @@ func TestSupervisorLogin(t *testing.T) {
 				requireSuccessfulLDAPIdentityProviderConditions(t, ldapIDP, expectedMsg)
 				return ldapIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamLDAP.TestUserMailAttributeValue, // username to present to server during login
@@ -221,7 +231,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeLDAP, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.LDAP.UserDN)
@@ -235,7 +245,9 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+base64.RawURLEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeValue)),
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$"
+			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamLDAP.TestUserDirectGroupsDNs,
 		},
 		{
@@ -286,7 +298,7 @@ func TestSupervisorLogin(t *testing.T) {
 				requireSuccessfulLDAPIdentityProviderConditions(t, ldapIDP, expectedMsg)
 				return ldapIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamLDAP.TestUserCN,       // username to present to server during login
@@ -295,7 +307,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeLDAP, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.LDAP.UserDN)
@@ -309,7 +321,7 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+base64.RawURLEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeValue)),
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserDN) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string { return "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserDN) + "$" },
 			wantDownstreamIDTokenGroups:          env.SupervisorUpstreamLDAP.TestUserDirectGroupsCNs,
 		},
 		{
@@ -360,7 +372,7 @@ func TestSupervisorLogin(t *testing.T) {
 				requireSuccessfulLDAPIdentityProviderConditions(t, ldapIDP, expectedMsg)
 				return ldapIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamLDAP.TestUserMailAttributeValue, // username to present to server during login
@@ -438,7 +450,7 @@ func TestSupervisorLogin(t *testing.T) {
 				}, time.Minute, 500*time.Millisecond)
 				return ldapIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamLDAP.TestUserMailAttributeValue, // username to present to server during login
@@ -447,7 +459,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeLDAP, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.LDAP.UserDN)
@@ -460,7 +472,9 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+base64.RawURLEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeValue)),
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$"
+			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamLDAP.TestUserDirectGroupsDNs,
 		},
 		{
@@ -543,7 +557,7 @@ func TestSupervisorLogin(t *testing.T) {
 				}, time.Minute, 500*time.Millisecond)
 				return ldapIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamLDAP.TestUserMailAttributeValue, // username to present to server during login
@@ -552,7 +566,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeLDAP, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.LDAP.UserDN)
@@ -565,7 +579,9 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+base64.RawURLEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeValue)),
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$"
+			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamLDAP.TestUserDirectGroupsDNs,
 		},
 		{
@@ -604,7 +620,7 @@ func TestSupervisorLogin(t *testing.T) {
 				requireSuccessfulActiveDirectoryIdentityProviderConditions(t, adIDP, expectedMsg)
 				return adIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue, // username to present to server during login
@@ -613,7 +629,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeActiveDirectory, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.ActiveDirectory.UserDN)
@@ -627,7 +643,9 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+env.SupervisorUpstreamActiveDirectory.TestUserUniqueIDAttributeValue,
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue) + "$"
+			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamActiveDirectory.TestUserIndirectGroupsSAMAccountPlusDomainNames,
 		}, {
 			name: "activedirectory with custom options",
@@ -679,7 +697,7 @@ func TestSupervisorLogin(t *testing.T) {
 				requireSuccessfulActiveDirectoryIdentityProviderConditions(t, adIDP, expectedMsg)
 				return adIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamActiveDirectory.TestUserMailAttributeValue, // username to present to server during login
@@ -688,7 +706,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeActiveDirectory, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.ActiveDirectory.UserDN)
@@ -702,7 +720,9 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+env.SupervisorUpstreamActiveDirectory.TestUserUniqueIDAttributeValue,
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamActiveDirectory.TestUserMailAttributeValue) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamActiveDirectory.TestUserMailAttributeValue) + "$"
+			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamActiveDirectory.TestUserDirectGroupsDNs,
 		},
 		{
@@ -759,7 +779,7 @@ func TestSupervisorLogin(t *testing.T) {
 				}, time.Minute, 500*time.Millisecond)
 				return adIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue, // username to present to server during login
@@ -768,7 +788,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeActiveDirectory, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.ActiveDirectory.UserDN)
@@ -781,7 +801,9 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+env.SupervisorUpstreamActiveDirectory.TestUserUniqueIDAttributeValue,
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue) + "$"
+			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamActiveDirectory.TestUserIndirectGroupsSAMAccountPlusDomainNames,
 		},
 		{
@@ -853,7 +875,7 @@ func TestSupervisorLogin(t *testing.T) {
 				}, time.Minute, 500*time.Millisecond)
 				return adIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue, // username to present to server during login
@@ -862,7 +884,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _ string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeActiveDirectory, customSessionData.ProviderType)
 				require.NotEmpty(t, customSessionData.ActiveDirectory.UserDN)
@@ -875,9 +897,197 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+env.SupervisorUpstreamActiveDirectory.TestUserUniqueIDAttributeValue,
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamActiveDirectory.TestUserPrincipalNameValue) + "$"
+			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamActiveDirectory.TestUserIndirectGroupsSAMAccountPlusDomainNames,
 		},
+		{
+			name: "active directory login fails after the user password is changed",
+			maybeSkip: func(t *testing.T) {
+				t.Helper()
+				if len(env.ToolsNamespace) == 0 && !env.HasCapability(testlib.CanReachInternetLDAPPorts) {
+					t.Skip("LDAP integration test requires connectivity to an LDAP server")
+				}
+				if env.SupervisorUpstreamActiveDirectory.Host == "" {
+					t.Skip("Active Directory hostname not specified")
+				}
+			},
+			createIDP: func(t *testing.T) string {
+				t.Helper()
+				secret := testlib.CreateTestSecret(t, env.SupervisorNamespace, "ad-service-account", v1.SecretTypeBasicAuth,
+					map[string]string{
+						v1.BasicAuthUsernameKey: env.SupervisorUpstreamActiveDirectory.BindUsername,
+						v1.BasicAuthPasswordKey: env.SupervisorUpstreamActiveDirectory.BindPassword,
+					},
+				)
+				adIDP := testlib.CreateTestActiveDirectoryIdentityProvider(t, idpv1alpha1.ActiveDirectoryIdentityProviderSpec{
+					Host: env.SupervisorUpstreamActiveDirectory.Host,
+					TLS: &idpv1alpha1.TLSSpec{
+						CertificateAuthorityData: base64.StdEncoding.EncodeToString([]byte(env.SupervisorUpstreamActiveDirectory.CABundle)),
+					},
+					Bind: idpv1alpha1.ActiveDirectoryIdentityProviderBind{
+						SecretName: secret.Name,
+					},
+				}, idpv1alpha1.ActiveDirectoryPhaseReady)
+				expectedMsg := fmt.Sprintf(
+					`successfully able to connect to "%s" and bind as user "%s" [validated with Secret "%s" at version "%s"]`,
+					env.SupervisorUpstreamActiveDirectory.Host, env.SupervisorUpstreamActiveDirectory.BindUsername,
+					secret.Name, secret.ResourceVersion,
+				)
+				requireSuccessfulActiveDirectoryIdentityProviderConditions(t, adIDP, expectedMsg)
+				return adIDP.Name
+			},
+			createTestUser: func(t *testing.T) (string, string) {
+				return createFreshADTestUser(t, env)
+			},
+			deleteTestUser: func(t *testing.T, username string) {
+				deleteTestADUser(t, env, username)
+			},
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, testUserName, testUserPassword string, httpClient *http.Client) {
+				requestAuthorizationUsingCLIPasswordFlow(t,
+					downstreamAuthorizeURL,
+					testUserName,     // username to present to server during login
+					testUserPassword, // password to present to server during login
+					httpClient,
+					false,
+				)
+			},
+			breakRefreshSessionData: func(t *testing.T, sessionData *psession.PinnipedSession, _, username string) {
+				changeADTestUserPassword(t, env, username)
+			},
+			// we can't know the subject ahead of time because we created a new user and don't know their uid,
+			// so skip wantDownstreamIDTokenSubjectToMatch
+			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
+			wantDownstreamIDTokenUsernameToMatch: func(username string) string {
+				return "^" + regexp.QuoteMeta(username+"@"+env.SupervisorUpstreamActiveDirectory.Domain) + "$"
+			},
+			wantDownstreamIDTokenGroups: []string{}, // none for now.
+		},
+		{
+			name: "active directory login fails after the user is deactivated",
+			maybeSkip: func(t *testing.T) {
+				t.Helper()
+				if len(env.ToolsNamespace) == 0 && !env.HasCapability(testlib.CanReachInternetLDAPPorts) {
+					t.Skip("LDAP integration test requires connectivity to an LDAP server")
+				}
+				if env.SupervisorUpstreamActiveDirectory.Host == "" {
+					t.Skip("Active Directory hostname not specified")
+				}
+			},
+			createIDP: func(t *testing.T) string {
+				t.Helper()
+				secret := testlib.CreateTestSecret(t, env.SupervisorNamespace, "ad-service-account", v1.SecretTypeBasicAuth,
+					map[string]string{
+						v1.BasicAuthUsernameKey: env.SupervisorUpstreamActiveDirectory.BindUsername,
+						v1.BasicAuthPasswordKey: env.SupervisorUpstreamActiveDirectory.BindPassword,
+					},
+				)
+				adIDP := testlib.CreateTestActiveDirectoryIdentityProvider(t, idpv1alpha1.ActiveDirectoryIdentityProviderSpec{
+					Host: env.SupervisorUpstreamActiveDirectory.Host,
+					TLS: &idpv1alpha1.TLSSpec{
+						CertificateAuthorityData: base64.StdEncoding.EncodeToString([]byte(env.SupervisorUpstreamActiveDirectory.CABundle)),
+					},
+					Bind: idpv1alpha1.ActiveDirectoryIdentityProviderBind{
+						SecretName: secret.Name,
+					},
+				}, idpv1alpha1.ActiveDirectoryPhaseReady)
+				expectedMsg := fmt.Sprintf(
+					`successfully able to connect to "%s" and bind as user "%s" [validated with Secret "%s" at version "%s"]`,
+					env.SupervisorUpstreamActiveDirectory.Host, env.SupervisorUpstreamActiveDirectory.BindUsername,
+					secret.Name, secret.ResourceVersion,
+				)
+				requireSuccessfulActiveDirectoryIdentityProviderConditions(t, adIDP, expectedMsg)
+				return adIDP.Name
+			},
+			createTestUser: func(t *testing.T) (string, string) {
+				return createFreshADTestUser(t, env)
+			},
+			deleteTestUser: func(t *testing.T, username string) {
+				deleteTestADUser(t, env, username)
+			},
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, testUserName, testUserPassword string, httpClient *http.Client) {
+				requestAuthorizationUsingCLIPasswordFlow(t,
+					downstreamAuthorizeURL,
+					testUserName,     // username to present to server during login
+					testUserPassword, // password to present to server during login
+					httpClient,
+					false,
+				)
+			},
+			breakRefreshSessionData: func(t *testing.T, sessionData *psession.PinnipedSession, _, username string) {
+				deactivateADTestUser(t, env, username)
+			},
+			// we can't know the subject ahead of time because we created a new user and don't know their uid,
+			// so skip wantDownstreamIDTokenSubjectToMatch
+			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
+			wantDownstreamIDTokenUsernameToMatch: func(username string) string {
+				return "^" + regexp.QuoteMeta(username+"@"+env.SupervisorUpstreamActiveDirectory.Domain) + "$"
+			},
+			wantDownstreamIDTokenGroups: []string{}, // none for now.
+		},
+		{
+			name: "active directory login fails after the user is locked",
+			maybeSkip: func(t *testing.T) {
+				t.Helper()
+				if len(env.ToolsNamespace) == 0 && !env.HasCapability(testlib.CanReachInternetLDAPPorts) {
+					t.Skip("LDAP integration test requires connectivity to an LDAP server")
+				}
+				if env.SupervisorUpstreamActiveDirectory.Host == "" {
+					t.Skip("Active Directory hostname not specified")
+				}
+			},
+			createIDP: func(t *testing.T) string {
+				t.Helper()
+				secret := testlib.CreateTestSecret(t, env.SupervisorNamespace, "ad-service-account", v1.SecretTypeBasicAuth,
+					map[string]string{
+						v1.BasicAuthUsernameKey: env.SupervisorUpstreamActiveDirectory.BindUsername,
+						v1.BasicAuthPasswordKey: env.SupervisorUpstreamActiveDirectory.BindPassword,
+					},
+				)
+				adIDP := testlib.CreateTestActiveDirectoryIdentityProvider(t, idpv1alpha1.ActiveDirectoryIdentityProviderSpec{
+					Host: env.SupervisorUpstreamActiveDirectory.Host,
+					TLS: &idpv1alpha1.TLSSpec{
+						CertificateAuthorityData: base64.StdEncoding.EncodeToString([]byte(env.SupervisorUpstreamActiveDirectory.CABundle)),
+					},
+					Bind: idpv1alpha1.ActiveDirectoryIdentityProviderBind{
+						SecretName: secret.Name,
+					},
+				}, idpv1alpha1.ActiveDirectoryPhaseReady)
+				expectedMsg := fmt.Sprintf(
+					`successfully able to connect to "%s" and bind as user "%s" [validated with Secret "%s" at version "%s"]`,
+					env.SupervisorUpstreamActiveDirectory.Host, env.SupervisorUpstreamActiveDirectory.BindUsername,
+					secret.Name, secret.ResourceVersion,
+				)
+				requireSuccessfulActiveDirectoryIdentityProviderConditions(t, adIDP, expectedMsg)
+				return adIDP.Name
+			},
+			createTestUser: func(t *testing.T) (string, string) {
+				return createFreshADTestUser(t, env)
+			},
+			deleteTestUser: func(t *testing.T, username string) {
+				deleteTestADUser(t, env, username)
+			},
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, testUserName, testUserPassword string, httpClient *http.Client) {
+				requestAuthorizationUsingCLIPasswordFlow(t,
+					downstreamAuthorizeURL,
+					testUserName,     // username to present to server during login
+					testUserPassword, // password to present to server during login
+					httpClient,
+					false,
+				)
+			},
+			breakRefreshSessionData: func(t *testing.T, sessionData *psession.PinnipedSession, _, username string) {
+				lockADTestUser(t, env, username)
+			},
+			// we can't know the subject ahead of time because we created a new user and don't know their uid,
+			// so skip wantDownstreamIDTokenSubjectToMatch
+			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
+			wantDownstreamIDTokenUsernameToMatch: func(username string) string {
+				return "^" + regexp.QuoteMeta(username+"@"+env.SupervisorUpstreamActiveDirectory.Domain) + "$"
+			},
+			wantDownstreamIDTokenGroups: []string{},
+		},
 		{
 			name: "logging in to activedirectory with a deactivated user fails",
 			maybeSkip: func(t *testing.T) {
@@ -914,7 +1124,7 @@ func TestSupervisorLogin(t *testing.T) {
 				requireSuccessfulActiveDirectoryIdentityProviderConditions(t, adIDP, expectedMsg)
 				return adIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamActiveDirectory.TestDeactivatedUserSAMAccountNameValue, // username to present to server during login
@@ -975,7 +1185,7 @@ func TestSupervisorLogin(t *testing.T) {
 				requireSuccessfulLDAPIdentityProviderConditions(t, ldapIDP, expectedMsg)
 				return ldapIDP.Name
 			},
-			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _ string, httpClient *http.Client) {
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
 				requestAuthorizationUsingCLIPasswordFlow(t,
 					downstreamAuthorizeURL,
 					env.SupervisorUpstreamLDAP.TestUserMailAttributeValue, // username to present to server during login
@@ -984,7 +1194,7 @@ func TestSupervisorLogin(t *testing.T) {
 					false,
 				)
 			},
-			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, idpName string) {
+			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, idpName, _ string) {
 				// get the idp, update the config.
 				client := testlib.NewSupervisorClientset(t)
 				ctx, cancel := context.WithTimeout(context.Background(), 5*time.Minute)
@@ -1007,7 +1217,9 @@ func TestSupervisorLogin(t *testing.T) {
 					"&sub="+base64.RawURLEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeValue)),
 			) + "$",
 			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
-			wantDownstreamIDTokenUsernameToMatch: "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$",
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$"
+			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamLDAP.TestUserDirectGroupsDNs,
 		},
 	}
@@ -1020,6 +1232,8 @@ func TestSupervisorLogin(t *testing.T) {
 				tt.createIDP,
 				tt.requestAuthorization,
 				tt.breakRefreshSessionData,
+				tt.createTestUser,
+				tt.deleteTestUser,
 				tt.wantDownstreamIDTokenSubjectToMatch,
 				tt.wantDownstreamIDTokenUsernameToMatch,
 				tt.wantDownstreamIDTokenGroups,
@@ -1150,10 +1364,15 @@ func requireEventuallySuccessfulActiveDirectoryIdentityProviderConditions(t *tes
 func testSupervisorLogin(
 	t *testing.T,
 	createIDP func(t *testing.T) string,
-	requestAuthorization func(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL string, httpClient *http.Client),
+	requestAuthorization func(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL, username, password string, httpClient *http.Client),
-	breakRefreshSessionData func(t *testing.T, pinnipedSession *psession.PinnipedSession, idpName string),
+	breakRefreshSessionData func(t *testing.T, pinnipedSession *psession.PinnipedSession, idpName, username string),
-	wantDownstreamIDTokenSubjectToMatch, wantDownstreamIDTokenUsernameToMatch string, wantDownstreamIDTokenGroups []string,
+	createTestUser func(t *testing.T) (string, string),
-	wantErrorDescription string, wantErrorType string,
+	deleteTestUser func(t *testing.T, username string),
+	wantDownstreamIDTokenSubjectToMatch string,
+	wantDownstreamIDTokenUsernameToMatch func(username string) string,
+	wantDownstreamIDTokenGroups []string,
+	wantErrorDescription string,
+	wantErrorType string,
 ) {
 	env := testlib.IntegrationEnv(t)
 
@@ -1241,6 +1460,12 @@ func testSupervisorLogin(
 	// Create upstream IDP and wait for it to become ready.
 	idpName := createIDP(t)
 
+	username, password := "", ""
+	if createTestUser != nil {
+		username, password = createTestUser(t)
+		defer deleteTestUser(t, username)
+	}
+
 	// Perform OIDC discovery for our downstream.
 	var discovery *coreosoidc.Provider
 	testlib.RequireEventually(t, func(requireEventually *require.Assertions) {
@@ -1276,7 +1501,7 @@ func testSupervisorLogin(
 	)
 
 	// Perform parameterized auth code acquisition.
-	requestAuthorization(t, downstreamAuthorizeURL, localCallbackServer.URL, httpClient)
+	requestAuthorization(t, downstreamAuthorizeURL, localCallbackServer.URL, username, password, httpClient)
 
 	// Expect that our callback handler was invoked.
 	callback := localCallbackServer.waitForCallback(10 * time.Second)
@@ -1294,7 +1519,7 @@ func testSupervisorLogin(
 		expectedIDTokenClaims := []string{"iss", "exp", "sub", "aud", "auth_time", "iat", "jti", "nonce", "rat", "username", "groups"}
 		verifyTokenResponse(t,
 			tokenResponse, discovery, downstreamOAuth2Config, nonceParam,
-			expectedIDTokenClaims, wantDownstreamIDTokenSubjectToMatch, wantDownstreamIDTokenUsernameToMatch, wantDownstreamIDTokenGroups)
+			expectedIDTokenClaims, wantDownstreamIDTokenSubjectToMatch, wantDownstreamIDTokenUsernameToMatch(username), wantDownstreamIDTokenGroups)
 
 		// token exchange on the original token
 		doTokenExchange(t, &downstreamOAuth2Config, tokenResponse, httpClient, discovery)
@@ -1308,7 +1533,7 @@ func testSupervisorLogin(
 		expectRefreshedIDTokenClaims := []string{"iss", "exp", "sub", "aud", "auth_time", "iat", "jti", "rat", "username", "groups", "at_hash"}
 		verifyTokenResponse(t,
 			refreshedTokenResponse, discovery, downstreamOAuth2Config, "",
-			expectRefreshedIDTokenClaims, wantDownstreamIDTokenSubjectToMatch, wantDownstreamIDTokenUsernameToMatch, wantDownstreamIDTokenGroups)
+			expectRefreshedIDTokenClaims, wantDownstreamIDTokenSubjectToMatch, wantDownstreamIDTokenUsernameToMatch(username), wantDownstreamIDTokenGroups)
 
 		require.NotEqual(t, tokenResponse.AccessToken, refreshedTokenResponse.AccessToken)
 		require.NotEqual(t, tokenResponse.RefreshToken, refreshedTokenResponse.RefreshToken)
@@ -1333,7 +1558,7 @@ func testSupervisorLogin(
 			// Next mutate the part of the session that is used during upstream refresh.
 			pinnipedSession, ok := storedRefreshSession.GetSession().(*psession.PinnipedSession)
 			require.True(t, ok, "should have been able to cast session data to PinnipedSession")
-			breakRefreshSessionData(t, pinnipedSession, idpName)
+			breakRefreshSessionData(t, pinnipedSession, idpName, username)
 
 			// Then save the mutated Secret back to Kubernetes.
 			// There is no update function, so delete and create again at the same name.
@@ -1423,7 +1648,7 @@ func verifyTokenResponse(
 	require.NotEmpty(t, tokenResponse.RefreshToken)
 }
 
-func requestAuthorizationUsingBrowserAuthcodeFlow(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL string, httpClient *http.Client) {
+func requestAuthorizationUsingBrowserAuthcodeFlow(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL, _, _ string, httpClient *http.Client) {
 	t.Helper()
 	env := testlib.IntegrationEnv(t)
 
@@ -1595,3 +1820,153 @@ func expectSecurityHeaders(t *testing.T, response *http.Response, expectFositeTo
 	assert.Equal(t, "no-cache", h.Get("Pragma"))
 	assert.Equal(t, "0", h.Get("Expires"))
 }
+
+// create a fresh test user in AD to use for this test.
+func createFreshADTestUser(t *testing.T, env *testlib.TestEnv) (string, string) {
+	t.Helper()
+	// dial tls
+	conn := dialTLS(t, env)
+	// bind
+	err := conn.Bind(env.SupervisorUpstreamActiveDirectory.BindUsername, env.SupervisorUpstreamActiveDirectory.BindPassword)
+	require.NoError(t, err)
+
+	testUserName := "user-" + createRandomHexString(t, 7) // sAMAccountNames are limited to 20 characters, so this is as long as we can make it.
+	// create
+	userDN := fmt.Sprintf("CN=%s,OU=test-users,%s", testUserName, env.SupervisorUpstreamActiveDirectory.UserSearchBase)
+	a := ldap.NewAddRequest(userDN, []ldap.Control{})
+	a.Attribute("objectClass", []string{"top", "person", "organizationalPerson", "user"})
+	a.Attribute("userPrincipalName", []string{fmt.Sprintf("%s@%s", testUserName, env.SupervisorUpstreamActiveDirectory.Domain)})
+	a.Attribute("sAMAccountName", []string{testUserName})
+
+	err = conn.Add(a)
+	require.NoError(t, err)
+
+	// modify password and enable account
+	testUserPassword := createRandomASCIIString(t, 20)
+	enc := unicode.UTF16(unicode.LittleEndian, unicode.IgnoreBOM).NewEncoder()
+	encodedTestUserPassword, err := enc.String("\"" + testUserPassword + "\"")
+	require.NoError(t, err)
+
+	m := ldap.NewModifyRequest(userDN, []ldap.Control{})
+	m.Replace("unicodePwd", []string{encodedTestUserPassword})
+	m.Replace("userAccountControl", []string{"512"})
+	err = conn.Modify(m)
+	require.NoError(t, err)
+
+	time.Sleep(20 * time.Second) // intrasite domain controller replication can take up to 15 seconds, so wait to ensure the change has propogated.
+	return testUserName, testUserPassword
+}
+
+// deactivate the test user.
+func deactivateADTestUser(t *testing.T, env *testlib.TestEnv, testUserName string) {
+	conn := dialTLS(t, env)
+	// bind
+	err := conn.Bind(env.SupervisorUpstreamActiveDirectory.BindUsername, env.SupervisorUpstreamActiveDirectory.BindPassword)
+	require.NoError(t, err)
+
+	userDN := fmt.Sprintf("CN=%s,OU=test-users,%s", testUserName, env.SupervisorUpstreamActiveDirectory.UserSearchBase)
+	m := ldap.NewModifyRequest(userDN, []ldap.Control{})
+	m.Replace("userAccountControl", []string{"514"}) // normal user, account disabled
+	err = conn.Modify(m)
+	require.NoError(t, err)
+
+	time.Sleep(20 * time.Second) // intrasite domain controller replication can take up to 15 seconds, so wait to ensure the change has propogated.
+}
+
+// lock the test user's account by entering the wrong password a bunch of times.
+func lockADTestUser(t *testing.T, env *testlib.TestEnv, testUserName string) {
+	userDN := fmt.Sprintf("CN=%s,OU=test-users,%s", testUserName, env.SupervisorUpstreamActiveDirectory.UserSearchBase)
+	conn := dialTLS(t, env)
+
+	// our password policy allows 20 wrong attempts before locking the account, so do 21.
+	// these wrong password attempts could go to different domain controllers, but account
+	// lockout changes are urgently replicated, meaning that the domain controllers will be
+	// synced asap rather than in the usual 15 second interval.
+	// See https://docs.microsoft.com/en-us/previous-versions/windows/it-pro/windows-2000-server/cc961787(v=technet.10)#urgent-replication-of-account-lockout-changes
+	for i := 0; i <= 21; i++ {
+		err := conn.Bind(userDN, "not-the-right-password-"+fmt.Sprint(i))
+		require.Error(t, err) // this should be an error
+	}
+
+	err := conn.Bind(env.SupervisorUpstreamActiveDirectory.BindUsername, env.SupervisorUpstreamActiveDirectory.BindPassword)
+	require.NoError(t, err)
+
+	time.Sleep(20 * time.Second) // intrasite domain controller replication can take up to 15 seconds, so wait to ensure the change has propogated.
+}
+
+// change the user's password to a new one.
+func changeADTestUserPassword(t *testing.T, env *testlib.TestEnv, testUserName string) {
+	conn := dialTLS(t, env)
+	// bind
+	err := conn.Bind(env.SupervisorUpstreamActiveDirectory.BindUsername, env.SupervisorUpstreamActiveDirectory.BindPassword)
+	require.NoError(t, err)
+
+	newTestUserPassword := createRandomASCIIString(t, 20)
+	enc := unicode.UTF16(unicode.LittleEndian, unicode.IgnoreBOM).NewEncoder()
+	encodedTestUserPassword, err := enc.String(`"` + newTestUserPassword + `"`)
+	require.NoError(t, err)
+
+	userDN := fmt.Sprintf("CN=%s,OU=test-users,%s", testUserName, env.SupervisorUpstreamActiveDirectory.UserSearchBase)
+	m := ldap.NewModifyRequest(userDN, []ldap.Control{})
+	m.Replace("unicodePwd", []string{encodedTestUserPassword})
+	err = conn.Modify(m)
+	require.NoError(t, err)
+
+	time.Sleep(20 * time.Second) // intrasite domain controller replication can take up to 15 seconds, so wait to ensure the change has propogated.
+	// don't bother to return the new password... we won't be using it, just checking that it's changed.
+}
+
+// delete the test user created for this test.
+func deleteTestADUser(t *testing.T, env *testlib.TestEnv, testUserName string) {
+	t.Helper()
+	conn := dialTLS(t, env)
+	// bind
+	err := conn.Bind(env.SupervisorUpstreamActiveDirectory.BindUsername, env.SupervisorUpstreamActiveDirectory.BindPassword)
+	require.NoError(t, err)
+
+	userDN := fmt.Sprintf("CN=%s,OU=test-users,%s", testUserName, env.SupervisorUpstreamActiveDirectory.UserSearchBase)
+	d := ldap.NewDelRequest(userDN, []ldap.Control{})
+	err = conn.Del(d)
+	require.NoError(t, err)
+}
+
+func dialTLS(t *testing.T, env *testlib.TestEnv) *ldap.Conn {
+	t.Helper()
+	// dial tls
+	rootCAs := x509.NewCertPool()
+	success := rootCAs.AppendCertsFromPEM([]byte(env.SupervisorUpstreamActiveDirectory.CABundle))
+	require.True(t, success)
+	tlsConfig := ptls.DefaultLDAP(rootCAs)
+	dialer := &tls.Dialer{NetDialer: &net.Dialer{Timeout: time.Minute}, Config: tlsConfig}
+	c, err := dialer.DialContext(context.Background(), "tcp", env.SupervisorUpstreamActiveDirectory.Host)
+	require.NoError(t, err)
+	conn := ldap.NewConn(c, true)
+	conn.Start()
+	return conn
+}
+
+func createRandomHexString(t *testing.T, length int) string {
+	t.Helper()
+	bytes := make([]byte, length)
+	_, err := rand.Read(bytes)
+	require.NoError(t, err)
+	randomString := hex.EncodeToString(bytes)
+	return randomString
+}
+
+func createRandomASCIIString(t *testing.T, length int) string {
+	result := ""
+	for {
+		if len(result) >= length {
+			return result
+		}
+		num, err := rand.Int(rand.Reader, big.NewInt(int64(127)))
+		require.NoError(t, err)
+		n := num.Int64()
+		// Make sure that the number/byte/letter is inside
+		// the range of printable ASCII characters (excluding space and DEL)
+		if n > 32 && n < 127 {
+			result += string(rune(n))
+		}
+	}
+}

test/testlib/env.go

@@ -84,6 +84,7 @@ type TestOIDCUpstream struct {
 
 type TestLDAPUpstream struct {
 	Host                                            string   `json:"host"`
+	Domain                                          string   `json:"domain"`
 	StartTLSOnlyHost                                string   `json:"startTLSOnlyHost"`
 	CABundle                                        string   `json:"caBundle"`
 	BindUsername                                    string   `json:"bindUsername"`
@@ -279,6 +280,7 @@ func loadEnvVars(t *testing.T, result *TestEnv) {
 
 	result.SupervisorUpstreamActiveDirectory = TestLDAPUpstream{
 		Host:                                  wantEnv("PINNIPED_TEST_AD_HOST", ""),
+		Domain:                                wantEnv("PINNIPED_TEST_AD_DOMAIN", ""),
 		CABundle:                              base64Decoded(t, os.Getenv("PINNIPED_TEST_AD_LDAPS_CA_BUNDLE")),
 		BindUsername:                          wantEnv("PINNIPED_TEST_AD_BIND_ACCOUNT_USERNAME", ""),
 		BindPassword:                          wantEnv("PINNIPED_TEST_AD_BIND_ACCOUNT_PASSWORD", ""),