Merge branch 'main' into proposal_process

internal/oidc/provider/dynamic_upstream_idp_provider.go

@@ -108,7 +108,7 @@ type UpstreamLDAPIdentityProviderI interface {
 	authenticators.UserAuthenticator
 
 	// PerformRefresh performs a refresh against the upstream LDAP identity provider
-	PerformRefresh(ctx context.Context, storedRefreshAttributes StoredRefreshAttributes) error
+	PerformRefresh(ctx context.Context, storedRefreshAttributes StoredRefreshAttributes) (groups []string, err error)
 }
 
 type StoredRefreshAttributes struct {

internal/oidc/token/token_handler.go

@@ -301,7 +301,7 @@ func upstreamLDAPRefresh(ctx context.Context, providerCache oidc.UpstreamIdentit
 		return errorsx.WithStack(errMissingUpstreamSessionInternalError)
 	}
 	// run PerformRefresh
-	err = p.PerformRefresh(ctx, provider.StoredRefreshAttributes{
+	groups, err := p.PerformRefresh(ctx, provider.StoredRefreshAttributes{
 		Username:             username,
 		Subject:              subject,
 		DN:                   dn,
@@ -312,6 +312,8 @@ func upstreamLDAPRefresh(ctx context.Context, providerCache oidc.UpstreamIdentit
 			"Upstream refresh failed.").WithWrap(err).
 			WithDebugf("provider name: %q, provider type: %q", s.ProviderName, s.ProviderType))
 	}
+	// Replace the old value with the new value.
+	session.Fosite.Claims.Extra[oidc.DownstreamGroupsClaim] = groups
 
 	return nil
 }

internal/oidc/token/token_handler_test.go

@@ -1339,6 +1339,60 @@ func TestRefreshGrant(t *testing.T) {
 				},
 			},
 		},
+		{
+			name: "happy path refresh grant when the upstream refresh returns new group memberships from LDAP, it updates groups",
+			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithLDAP(&oidctestutil.TestUpstreamLDAPIdentityProvider{
+				Name:                 ldapUpstreamName,
+				ResourceUID:          ldapUpstreamResourceUID,
+				URL:                  ldapUpstreamURL,
+				PerformRefreshGroups: []string{"new-group1", "new-group2", "new-group3"},
+			}),
+			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.StatusOK,
+					wantSuccessBodyFields:       []string{"refresh_token", "access_token", "id_token", "token_type", "expires_in", "scope"},
+					wantRequestedScopes:         []string{"openid", "offline_access"},
+					wantGrantedScopes:           []string{"openid", "offline_access"},
+					wantGroups:                  []string{"new-group1", "new-group2", "new-group3"},
+					wantUpstreamRefreshCall:     happyLDAPUpstreamRefreshCall(),
+					wantCustomSessionDataStored: happyLDAPCustomSessionData,
+				},
+			},
+		},
+		{
+			name: "happy path refresh grant when the upstream refresh returns empty list of group memberships from LDAP, it updates groups to an empty list",
+			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithLDAP(&oidctestutil.TestUpstreamLDAPIdentityProvider{
+				Name:                 ldapUpstreamName,
+				ResourceUID:          ldapUpstreamResourceUID,
+				URL:                  ldapUpstreamURL,
+				PerformRefreshGroups: []string{},
+			}),
+			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.StatusOK,
+					wantSuccessBodyFields:       []string{"refresh_token", "access_token", "id_token", "token_type", "expires_in", "scope"},
+					wantRequestedScopes:         []string{"openid", "offline_access"},
+					wantGrantedScopes:           []string{"openid", "offline_access"},
+					wantGroups:                  []string{},
+					wantUpstreamRefreshCall:     happyLDAPUpstreamRefreshCall(),
+					wantCustomSessionDataStored: happyLDAPCustomSessionData,
+				},
+			},
+		},
 		{
 			name: "error from refresh grant when the upstream refresh does not return new group memberships from the merged ID token and userinfo results by returning group claim with illegal nil value",
 			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithOIDC(
@@ -1967,9 +2021,10 @@ func TestRefreshGrant(t *testing.T) {
 		{
 			name: "upstream ldap refresh happy path",
 			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithLDAP(&oidctestutil.TestUpstreamLDAPIdentityProvider{
-				Name:        ldapUpstreamName,
+				Name:                 ldapUpstreamName,
-				ResourceUID: ldapUpstreamResourceUID,
+				ResourceUID:          ldapUpstreamResourceUID,
-				URL:         ldapUpstreamURL,
+				URL:                  ldapUpstreamURL,
+				PerformRefreshGroups: goodGroups,
 			}),
 			authcodeExchange: authcodeExchangeInputs{
 				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },
@@ -1987,9 +2042,10 @@ func TestRefreshGrant(t *testing.T) {
 		{
 			name: "upstream active directory refresh happy path",
 			idps: oidctestutil.NewUpstreamIDPListerBuilder().WithActiveDirectory(&oidctestutil.TestUpstreamLDAPIdentityProvider{
-				Name:        activeDirectoryUpstreamName,
+				Name:                 activeDirectoryUpstreamName,
-				ResourceUID: activeDirectoryUpstreamResourceUID,
+				ResourceUID:          activeDirectoryUpstreamResourceUID,
-				URL:         ldapUpstreamURL,
+				URL:                  ldapUpstreamURL,
+				PerformRefreshGroups: goodGroups,
 			}),
 			authcodeExchange: authcodeExchangeInputs{
 				modifyAuthRequest: func(r *http.Request) { r.Form.Set("scope", "openid offline_access") },

internal/testutil/oidctestutil/oidctestutil.go

@@ -101,6 +101,7 @@ type TestUpstreamLDAPIdentityProvider struct {
 	performRefreshCallCount int
 	performRefreshArgs      []*PerformRefreshArgs
 	PerformRefreshErr       error
+	PerformRefreshGroups    []string
 }
 
 var _ provider.UpstreamLDAPIdentityProviderI = &TestUpstreamLDAPIdentityProvider{}
@@ -121,7 +122,7 @@ func (u *TestUpstreamLDAPIdentityProvider) GetURL() *url.URL {
 	return u.URL
 }
 
-func (u *TestUpstreamLDAPIdentityProvider) PerformRefresh(ctx context.Context, storedRefreshAttributes provider.StoredRefreshAttributes) error {
+func (u *TestUpstreamLDAPIdentityProvider) PerformRefresh(ctx context.Context, storedRefreshAttributes provider.StoredRefreshAttributes) ([]string, error) {
 	if u.performRefreshArgs == nil {
 		u.performRefreshArgs = make([]*PerformRefreshArgs, 0)
 	}
@@ -133,9 +134,9 @@ func (u *TestUpstreamLDAPIdentityProvider) PerformRefresh(ctx context.Context, s
 		ExpectedSubject:  storedRefreshAttributes.Subject,
 	})
 	if u.PerformRefreshErr != nil {
-		return u.PerformRefreshErr
+		return nil, u.PerformRefreshErr
 	}
-	return nil
+	return u.PerformRefreshGroups, nil
 }
 
 func (u *TestUpstreamLDAPIdentityProvider) PerformRefreshCallCount() int {

internal/upstreamldap/upstreamldap.go

@@ -13,12 +13,12 @@ import (
 	"fmt"
 	"net"
 	"net/url"
-	"sort"
 	"strings"
 	"time"
 
 	"github.com/go-ldap/ldap/v3"
 	"k8s.io/apimachinery/pkg/types"
+	"k8s.io/apimachinery/pkg/util/sets"
 	"k8s.io/apiserver/pkg/authentication/user"
 	"k8s.io/utils/trace"
 
@@ -170,61 +170,11 @@ func (p *Provider) GetConfig() ProviderConfig {
 	return p.c
 }
 
-func (p *Provider) PerformRefresh(ctx context.Context, storedRefreshAttributes provider.StoredRefreshAttributes) error {
+func (p *Provider) PerformRefresh(ctx context.Context, storedRefreshAttributes provider.StoredRefreshAttributes) ([]string, 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)
-		return err
-	}
-
-	// if any more or less than one entry, error.
-	// we don't need to worry about logging this because we know it's a dn.
-	if len(searchResult.Entries) != 1 {
-		return fmt.Errorf(`searching for user %q resulted in %d search results, but expected 1 result`,
-			userDN, len(searchResult.Entries),
-		)
-	}
-
-	userEntry := searchResult.Entries[0]
-	if len(userEntry.DN) == 0 {
-		return fmt.Errorf(`searching for user with original DN %q resulted in search result without DN`, userDN)
-	}
-
-	newUsername, err := p.getSearchResultAttributeValue(p.c.UserSearch.UsernameAttribute, userEntry, userDN)
-	if err != nil {
-		return err
-	}
-	if newUsername != storedRefreshAttributes.Username {
-		return fmt.Errorf(`searching for user %q returned a different username than the previous value. expected: %q, actual: %q`,
-			userDN, storedRefreshAttributes.Username, newUsername,
-		)
-	}
-
-	newUID, err := p.getSearchResultAttributeRawValueEncoded(p.c.UserSearch.UIDAttribute, userEntry, userDN)
-	if err != nil {
-		return err
-	}
-	newSubject := downstreamsession.DownstreamLDAPSubject(newUID, *p.GetURL())
-	if newSubject != storedRefreshAttributes.Subject {
-		return fmt.Errorf(`searching for user %q produced a different subject than the previous value. expected: %q, actual: %q`, userDN, storedRefreshAttributes.Subject, newSubject)
-	}
-	for attribute, validateFunc := range p.c.RefreshAttributeChecks {
-		err = validateFunc(userEntry, storedRefreshAttributes)
-		if err != nil {
-			return fmt.Errorf(`validation for attribute %q 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
-}
-
-func (p *Provider) performRefresh(ctx context.Context, userDN string) (*ldap.SearchResult, error) {
-	search := p.refreshUserSearchRequest(userDN)
-
 	conn, err := p.dial(ctx)
 	if err != nil {
 		return nil, fmt.Errorf(`error dialing host %q: %w`, p.c.Host, err)
@@ -236,6 +186,60 @@ func (p *Provider) performRefresh(ctx context.Context, userDN string) (*ldap.Sea
 		return nil, fmt.Errorf(`error binding as %q before user search: %w`, p.c.BindUsername, err)
 	}
 
+	searchResult, err := p.performUserRefreshSearch(conn, userDN)
+	if err != nil {
+		p.traceRefreshFailure(t, err)
+		return nil, err
+	}
+
+	// if any more or less than one entry, error.
+	// we don't need to worry about logging this because we know it's a dn.
+	if len(searchResult.Entries) != 1 {
+		return nil, fmt.Errorf(`searching for user %q resulted in %d search results, but expected 1 result`,
+			userDN, len(searchResult.Entries),
+		)
+	}
+
+	userEntry := searchResult.Entries[0]
+	if len(userEntry.DN) == 0 {
+		return nil, fmt.Errorf(`searching for user with original DN %q resulted in search result without DN`, userDN)
+	}
+
+	newUsername, err := p.getSearchResultAttributeValue(p.c.UserSearch.UsernameAttribute, userEntry, userDN)
+	if err != nil {
+		return nil, err
+	}
+	if newUsername != storedRefreshAttributes.Username {
+		return nil, fmt.Errorf(`searching for user %q returned a different username than the previous value. expected: %q, actual: %q`,
+			userDN, storedRefreshAttributes.Username, newUsername,
+		)
+	}
+
+	newUID, err := p.getSearchResultAttributeRawValueEncoded(p.c.UserSearch.UIDAttribute, userEntry, userDN)
+	if err != nil {
+		return nil, err
+	}
+	newSubject := downstreamsession.DownstreamLDAPSubject(newUID, *p.GetURL())
+	if newSubject != storedRefreshAttributes.Subject {
+		return nil, fmt.Errorf(`searching for user %q produced a different subject than the previous value. expected: %q, actual: %q`, userDN, storedRefreshAttributes.Subject, newSubject)
+	}
+	for attribute, validateFunc := range p.c.RefreshAttributeChecks {
+		err = validateFunc(userEntry, storedRefreshAttributes)
+		if err != nil {
+			return nil, fmt.Errorf(`validation for attribute %q failed during upstream refresh: %w`, attribute, err)
+		}
+	}
+
+	mappedGroupNames, err := p.searchGroupsForUserDN(conn, userDN)
+	if err != nil {
+		return nil, err
+	}
+	return mappedGroupNames, nil
+}
+
+func (p *Provider) performUserRefreshSearch(conn Conn, userDN string) (*ldap.SearchResult, error) {
+	search := p.refreshUserSearchRequest(userDN)
+
 	searchResult, err := conn.Search(search)
 
 	if err != nil {
@@ -445,6 +449,11 @@ func (p *Provider) authenticateUserImpl(ctx context.Context, username string, bi
 }
 
 func (p *Provider) searchGroupsForUserDN(conn Conn, userDN string) ([]string, error) {
+	// If we do not have group search configured, skip this search.
+	if len(p.c.GroupSearch.Base) == 0 {
+		return []string{}, nil
+	}
+
 	searchResult, err := conn.SearchWithPaging(p.groupSearchRequest(userDN), groupSearchPageSize)
 	if err != nil {
 		return nil, fmt.Errorf(`error searching for group memberships for user with DN %q: %w`, userDN, err)
@@ -455,7 +464,7 @@ func (p *Provider) searchGroupsForUserDN(conn Conn, userDN string) ([]string, er
 		groupAttributeName = distinguishedNameAttributeName
 	}
 
-	var groups []string
+	groups := []string{}
 entries:
 	for _, groupEntry := range searchResult.Entries {
 		if len(groupEntry.DN) == 0 {
@@ -476,8 +485,9 @@ entries:
 		}
 		groups = append(groups, mappedGroupName)
 	}
-
+	// de-duplicate the list of groups by turning it into a set,
-	return groups, nil
+	// then turn it back into a sorted list.
+	return sets.NewString(groups...).List(), nil
 }
 
 func (p *Provider) validateConfig() error {
@@ -567,14 +577,10 @@ func (p *Provider) searchAndBindUser(conn Conn, username string, bindFunc func(c
 		return nil, err
 	}
 
-	var mappedGroupNames []string
+	mappedGroupNames, err := p.searchGroupsForUserDN(conn, userEntry.DN)
-	if len(p.c.GroupSearch.Base) > 0 {
+	if err != nil {
-		mappedGroupNames, err = p.searchGroupsForUserDN(conn, userEntry.DN)
+		return nil, err
-		if err != nil {
-			return nil, err
-		}
 	}
-	sort.Strings(mappedGroupNames)
 
 	mappedRefreshAttributes := make(map[string]string)
 	for k := range p.c.RefreshAttributeChecks {

internal/upstreamldap/upstreamldap_test.go

@@ -237,6 +237,33 @@ func TestEndUserAuthentication(t *testing.T) {
 			},
 			wantAuthResponse: expectedAuthResponse(nil),
 		},
+		{
+			name:     "when the group search has an override func",
+			username: testUpstreamUsername,
+			password: testUpstreamPassword,
+			providerConfig: providerConfig(func(p *ProviderConfig) {
+				p.GroupAttributeParsingOverrides = map[string]func(*ldap.Entry) (string, error){testGroupSearchGroupNameAttribute: func(entry *ldap.Entry) (string, error) {
+					return "something-else-" + entry.DN, 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().SearchWithPaging(expectedGroupSearch(nil), expectedGroupSearchPageSize).
+					Return(exampleGroupSearchResult, nil).Times(1)
+				conn.EXPECT().Close().Times(1)
+			},
+			bindEndUserMocks: func(conn *mockldapconn.MockConn) {
+				conn.EXPECT().Bind(testUserSearchResultDNValue, testUpstreamPassword).Times(1)
+			},
+			wantAuthResponse: expectedAuthResponse(func(r *authenticators.Response) {
+				r.User = &user.DefaultInfo{
+					Name:   testUserSearchResultUsernameAttributeValue,
+					UID:    base64.RawURLEncoding.EncodeToString([]byte(testUserSearchResultUIDAttributeValue)),
+					Groups: []string{"something-else-some-upstream-group-dn1", "something-else-some-upstream-group-dn2"},
+				}
+			}),
+		},
 		{
 			name:     "when the group search base is empty then skip the group search entirely",
 			username: testUpstreamUsername,
@@ -254,7 +281,7 @@ func TestEndUserAuthentication(t *testing.T) {
 			},
 			wantAuthResponse: expectedAuthResponse(func(r *authenticators.Response) {
 				info := r.User.(*user.DefaultInfo)
-				info.Groups = nil
+				info.Groups = []string{}
 			}),
 		},
 		{
@@ -958,6 +985,24 @@ func TestEndUserAuthentication(t *testing.T) {
 			},
 			wantError: fmt.Sprintf(`found empty value for attribute "%s" while searching for user "%s", but expected value to be non-empty`, testUserSearchUIDAttribute, testUpstreamUsername),
 		},
+		{
+			name:     "when the group search has an override func that errors",
+			username: testUpstreamUsername,
+			password: testUpstreamPassword,
+			providerConfig: providerConfig(func(p *ProviderConfig) {
+				p.GroupAttributeParsingOverrides = map[string]func(*ldap.Entry) (string, error){testGroupSearchGroupNameAttribute: func(entry *ldap.Entry) (string, error) {
+					return "", errors.New("some error")
+				}}
+			}),
+			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(nil), expectedGroupSearchPageSize).
+					Return(exampleGroupSearchResult, nil).Times(1)
+				conn.EXPECT().Close().Times(1)
+			},
+			wantError: fmt.Sprintf("error finding groups for user %s: some error", testUserSearchResultDNValue),
+		},
 		{
 			name:           "when binding as the found user returns an error",
 			username:       testUpstreamUsername,
@@ -1100,6 +1145,18 @@ func TestUpstreamRefresh(t *testing.T) {
 		Controls:     nil, // don't need paging because we set the SizeLimit so small
 	}
 
+	expectedGroupSearch := &ldap.SearchRequest{
+		BaseDN:       testGroupSearchBase,
+		Scope:        ldap.ScopeWholeSubtree,
+		DerefAliases: ldap.NeverDerefAliases,
+		SizeLimit:    0, // unlimited size because we will search with paging
+		TimeLimit:    90,
+		TypesOnly:    false,
+		Filter:       testGroupSearchFilterInterpolated,
+		Attributes:   []string{testGroupSearchGroupNameAttribute},
+		Controls:     nil, // nil because ldap.SearchWithPaging() will set the appropriate controls for us
+	}
+
 	happyPathUserSearchResult := &ldap.SearchResult{
 		Entries: []*ldap.Entry{
 			{
@@ -1146,6 +1203,7 @@ func TestUpstreamRefresh(t *testing.T) {
 		setupMocks     func(conn *mockldapconn.MockConn)
 		dialError      error
 		wantErr        string
+		wantGroups     []string
 	}{
 		{
 			name:           "happy path where searching the dn returns a single entry",
@@ -1155,6 +1213,90 @@ func TestUpstreamRefresh(t *testing.T) {
 				conn.EXPECT().Search(expectedUserSearch).Return(happyPathUserSearchResult, nil).Times(1)
 				conn.EXPECT().Close().Times(1)
 			},
+			wantGroups: []string{},
+		},
+		{
+			name: "happy path where group search returns groups",
+			providerConfig: &ProviderConfig{
+				Name:               "some-provider-name",
+				Host:               testHost,
+				CABundle:           nil, // this field is only used by the production dialer, which is replaced by a mock for this test
+				ConnectionProtocol: TLS,
+				BindUsername:       testBindUsername,
+				BindPassword:       testBindPassword,
+				UserSearch: UserSearchConfig{
+					Base:              testUserSearchBase,
+					UIDAttribute:      testUserSearchUIDAttribute,
+					UsernameAttribute: testUserSearchUsernameAttribute,
+				},
+				GroupSearch: GroupSearchConfig{
+					Base:               testGroupSearchBase,
+					Filter:             testGroupSearchFilter,
+					GroupNameAttribute: testGroupSearchGroupNameAttribute,
+				},
+				RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+					pwdLastSetAttribute: AttributeUnchangedSinceLogin(pwdLastSetAttribute),
+				},
+			},
+			setupMocks: func(conn *mockldapconn.MockConn) {
+				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
+				conn.EXPECT().Search(expectedUserSearch).Return(happyPathUserSearchResult, nil).Times(1)
+				conn.EXPECT().SearchWithPaging(expectedGroupSearch, expectedGroupSearchPageSize).Return(&ldap.SearchResult{
+					Entries: []*ldap.Entry{
+						{
+							DN: testGroupSearchResultDNValue1,
+							Attributes: []*ldap.EntryAttribute{
+								ldap.NewEntryAttribute(testGroupSearchGroupNameAttribute, []string{testGroupSearchResultGroupNameAttributeValue1}),
+							},
+						},
+						{
+							DN: testGroupSearchResultDNValue2,
+							Attributes: []*ldap.EntryAttribute{
+								ldap.NewEntryAttribute(testGroupSearchGroupNameAttribute, []string{testGroupSearchResultGroupNameAttributeValue2}),
+							},
+						},
+					},
+					Referrals: []string{}, // note that we are not following referrals at this time
+					Controls:  []ldap.Control{},
+				}, nil).Times(1)
+				conn.EXPECT().Close().Times(1)
+			},
+			wantGroups: []string{testGroupSearchResultGroupNameAttributeValue1, testGroupSearchResultGroupNameAttributeValue2},
+		},
+		{
+			name: "happy path where group search returns no groups",
+			providerConfig: &ProviderConfig{
+				Name:               "some-provider-name",
+				Host:               testHost,
+				CABundle:           nil, // this field is only used by the production dialer, which is replaced by a mock for this test
+				ConnectionProtocol: TLS,
+				BindUsername:       testBindUsername,
+				BindPassword:       testBindPassword,
+				UserSearch: UserSearchConfig{
+					Base:              testUserSearchBase,
+					UIDAttribute:      testUserSearchUIDAttribute,
+					UsernameAttribute: testUserSearchUsernameAttribute,
+				},
+				GroupSearch: GroupSearchConfig{
+					Base:               testGroupSearchBase,
+					Filter:             testGroupSearchFilter,
+					GroupNameAttribute: testGroupSearchGroupNameAttribute,
+				},
+				RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+					pwdLastSetAttribute: AttributeUnchangedSinceLogin(pwdLastSetAttribute),
+				},
+			},
+			setupMocks: func(conn *mockldapconn.MockConn) {
+				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
+				conn.EXPECT().Search(expectedUserSearch).Return(happyPathUserSearchResult, nil).Times(1)
+				conn.EXPECT().SearchWithPaging(expectedGroupSearch, expectedGroupSearchPageSize).Return(&ldap.SearchResult{
+					Entries:   []*ldap.Entry{},
+					Referrals: []string{}, // note that we are not following referrals at this time
+					Controls:  []ldap.Control{},
+				}, nil).Times(1)
+				conn.EXPECT().Close().Times(1)
+			},
+			wantGroups: []string{},
 		},
 		{
 			name:           "error where dial fails",
@@ -1421,6 +1563,37 @@ func TestUpstreamRefresh(t *testing.T) {
 			},
 			wantErr: "validation for attribute \"pwdLastSet\" failed during upstream refresh: value for attribute \"pwdLastSet\" has changed since initial value at login",
 		},
+		{
+			name: "group search returns an error",
+			providerConfig: &ProviderConfig{
+				Name:               "some-provider-name",
+				Host:               testHost,
+				CABundle:           nil, // this field is only used by the production dialer, which is replaced by a mock for this test
+				ConnectionProtocol: TLS,
+				BindUsername:       testBindUsername,
+				BindPassword:       testBindPassword,
+				UserSearch: UserSearchConfig{
+					Base:              testUserSearchBase,
+					UIDAttribute:      testUserSearchUIDAttribute,
+					UsernameAttribute: testUserSearchUsernameAttribute,
+				},
+				GroupSearch: GroupSearchConfig{
+					Base:               testGroupSearchBase,
+					Filter:             testGroupSearchFilter,
+					GroupNameAttribute: testGroupSearchGroupNameAttribute,
+				},
+				RefreshAttributeChecks: map[string]func(*ldap.Entry, provider.StoredRefreshAttributes) error{
+					pwdLastSetAttribute: AttributeUnchangedSinceLogin(pwdLastSetAttribute),
+				},
+			},
+			setupMocks: func(conn *mockldapconn.MockConn) {
+				conn.EXPECT().Bind(testBindUsername, testBindPassword).Times(1)
+				conn.EXPECT().Search(expectedUserSearch).Return(happyPathUserSearchResult, nil).Times(1)
+				conn.EXPECT().SearchWithPaging(expectedGroupSearch, expectedGroupSearchPageSize).Return(nil, errors.New("some search error")).Times(1)
+				conn.EXPECT().Close().Times(1)
+			},
+			wantErr: "error searching for group memberships for user with DN \"some-upstream-user-dn\": some search error",
+		},
 	}
 
 	for _, tt := range tests {
@@ -1435,9 +1608,9 @@ func TestUpstreamRefresh(t *testing.T) {
 			}
 
 			dialWasAttempted := false
-			providerConfig.Dialer = LDAPDialerFunc(func(ctx context.Context, addr endpointaddr.HostPort) (Conn, error) {
+			tt.providerConfig.Dialer = LDAPDialerFunc(func(ctx context.Context, addr endpointaddr.HostPort) (Conn, error) {
 				dialWasAttempted = true
-				require.Equal(t, providerConfig.Host, addr.Endpoint())
+				require.Equal(t, tt.providerConfig.Host, addr.Endpoint())
 				if tt.dialError != nil {
 					return nil, tt.dialError
 				}
@@ -1446,9 +1619,9 @@ func TestUpstreamRefresh(t *testing.T) {
 			})
 
 			initialPwdLastSetEncoded := base64.RawURLEncoding.EncodeToString([]byte("132801740800000000"))
-			ldapProvider := New(*providerConfig)
+			ldapProvider := New(*tt.providerConfig)
 			subject := "ldaps://ldap.example.com:8443?base=some-upstream-user-base-dn&sub=c29tZS11cHN0cmVhbS11aWQtdmFsdWU"
-			err := ldapProvider.PerformRefresh(context.Background(), provider.StoredRefreshAttributes{
+			groups, err := ldapProvider.PerformRefresh(context.Background(), provider.StoredRefreshAttributes{
 				Username:             testUserSearchResultUsernameAttributeValue,
 				Subject:              subject,
 				DN:                   testUserSearchResultDNValue,
@@ -1461,6 +1634,7 @@ func TestUpstreamRefresh(t *testing.T) {
 				require.NoError(t, err)
 			}
 			require.Equal(t, true, dialWasAttempted)
+			require.Equal(t, tt.wantGroups, groups)
 		})
 	}
 }

test/integration/ldap_client_test.go

@@ -244,7 +244,7 @@ func TestLDAPSearch_Parallel(t *testing.T) {
 				p.GroupSearch.Base = ""
 			})),
 			wantAuthResponse: &authenticators.Response{
-				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: nil},
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}},
 				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
 				ExtraRefreshAttributes: map[string]string{},
 			},
@@ -257,7 +257,7 @@ 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: nil},
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}},
 				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
 				ExtraRefreshAttributes: map[string]string{},
 			},
@@ -302,7 +302,7 @@ 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"}},
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{"groupOfNames"}},
 				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
 				ExtraRefreshAttributes: map[string]string{},
 			},
@@ -328,7 +328,7 @@ 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: nil},
+				User:                   &user.DefaultInfo{Name: "pinny", UID: b64("1000"), Groups: []string{}},
 				DN:                     "cn=pinny,ou=users,dc=pinniped,dc=dev",
 				ExtraRefreshAttributes: map[string]string{},
 			},

test/integration/supervisor_login_test.go

@@ -51,21 +51,25 @@ func TestSupervisorLogin_Browser(t *testing.T) {
 	env := testlib.IntegrationEnv(t)
 
 	tests := []struct {
-		name                                 string
+		name                                    string
-		maybeSkip                            func(t *testing.T)
+		maybeSkip                               func(t *testing.T)
-		createTestUser                       func(t *testing.T) (string, string)
+		createTestUser                          func(t *testing.T) (string, string)
-		deleteTestUser                       func(t *testing.T, username string)
+		deleteTestUser                          func(t *testing.T, username string)
-		requestAuthorization                 func(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL, username, password string, httpClient *http.Client)
+		requestAuthorization                    func(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL, username, password string, httpClient *http.Client)
-		createIDP                            func(t *testing.T) string
+		createIDP                               func(t *testing.T) string
-		wantDownstreamIDTokenSubjectToMatch  string
+		wantDownstreamIDTokenSubjectToMatch     string
-		wantDownstreamIDTokenUsernameToMatch func(username string) string
+		wantDownstreamIDTokenUsernameToMatch    func(username string) string
-		wantDownstreamIDTokenGroups          []string
+		wantDownstreamIDTokenGroups             []string
-		wantErrorDescription                 string
+		wantDownstreamIDTokenGroupsAfterRefresh []string
-		wantErrorType                        string
+		wantErrorDescription                    string
+		wantErrorType                           string
 
 		// Either revoke the user's session on the upstream provider, or manipulate 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, username string)
+		// Edit the refresh session data between the initial login and the refresh, which is expected to
+		// succeed.
+		editRefreshSessionDataWithoutBreaking func(t *testing.T, sessionData *psession.PinnipedSession, idpName, username string)
 	}{
 		{
 			name: "oidc with default username and groups claim settings",
@@ -128,6 +132,14 @@ func TestSupervisorLogin_Browser(t *testing.T) {
 			wantDownstreamIDTokenSubjectToMatch:  "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Issuer+"?sub=") + ".+",
 			wantDownstreamIDTokenUsernameToMatch: func(_ string) string { return "^" + regexp.QuoteMeta(env.SupervisorUpstreamOIDC.Username) + "$" },
 			wantDownstreamIDTokenGroups:          env.SupervisorUpstreamOIDC.ExpectedGroups,
+			editRefreshSessionDataWithoutBreaking: func(t *testing.T, sessionData *psession.PinnipedSession, _, _ string) {
+				// even if we update this group to the wrong thing, we expect that it will return to the correct
+				// value after we refresh.
+				// However if there are no expected groups then they will not update, so we should skip this.
+				if len(env.SupervisorUpstreamOIDC.ExpectedGroups) > 0 {
+					sessionData.Fosite.Claims.Extra["groups"] = []string{"some-wrong-group", "some-other-group"}
+				}
+			},
 		},
 		{
 			name: "oidc without refresh token",
@@ -272,6 +284,11 @@ func TestSupervisorLogin_Browser(t *testing.T) {
 					false,
 				)
 			},
+			editRefreshSessionDataWithoutBreaking: func(t *testing.T, sessionData *psession.PinnipedSession, _, _ string) {
+				// even if we update this group to the wrong thing, we expect that it will return to the correct
+				// value after we refresh.
+				sessionData.Fosite.Claims.Extra["groups"] = []string{"some-wrong-group", "some-other-group"}
+			},
 			breakRefreshSessionData: func(t *testing.T, pinnipedSession *psession.PinnipedSession, _, _ string) {
 				customSessionData := pinnipedSession.Custom
 				require.Equal(t, psession.ProviderTypeLDAP, customSessionData.ProviderType)
@@ -291,6 +308,94 @@ func TestSupervisorLogin_Browser(t *testing.T) {
 			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamLDAP.TestUserDirectGroupsDNs,
 		},
+		{
+			name: "ldap with email as username and group search base that doesn't return anything, and using an LDAP provider which supports TLS",
+			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.SupervisorUpstreamLDAP.UserSearchBase == env.SupervisorUpstreamLDAP.GroupSearchBase {
+					// This test relies on using the user search base as the group search base, to simulate
+					// searching for groups and not finding any.
+					// If the users and groups are stored in the same place, then we will get groups
+					// back, so this test wouldn't make sense.
+					t.Skip("must have a different user search base than group search base")
+				}
+			},
+			createIDP: func(t *testing.T) string {
+				t.Helper()
+				secret := testlib.CreateTestSecret(t, env.SupervisorNamespace, "ldap-service-account", v1.SecretTypeBasicAuth,
+					map[string]string{
+						v1.BasicAuthUsernameKey: env.SupervisorUpstreamLDAP.BindUsername,
+						v1.BasicAuthPasswordKey: env.SupervisorUpstreamLDAP.BindPassword,
+					},
+				)
+				ldapIDP := testlib.CreateTestLDAPIdentityProvider(t, idpv1alpha1.LDAPIdentityProviderSpec{
+					Host: env.SupervisorUpstreamLDAP.Host,
+					TLS: &idpv1alpha1.TLSSpec{
+						CertificateAuthorityData: base64.StdEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.CABundle)),
+					},
+					Bind: idpv1alpha1.LDAPIdentityProviderBind{
+						SecretName: secret.Name,
+					},
+					UserSearch: idpv1alpha1.LDAPIdentityProviderUserSearch{
+						Base:   env.SupervisorUpstreamLDAP.UserSearchBase,
+						Filter: "",
+						Attributes: idpv1alpha1.LDAPIdentityProviderUserSearchAttributes{
+							Username: env.SupervisorUpstreamLDAP.TestUserMailAttributeName,
+							UID:      env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeName,
+						},
+					},
+					GroupSearch: idpv1alpha1.LDAPIdentityProviderGroupSearch{
+						Base:   env.SupervisorUpstreamLDAP.UserSearchBase, // groups not stored at the user search base
+						Filter: "",
+						Attributes: idpv1alpha1.LDAPIdentityProviderGroupSearchAttributes{
+							GroupName: "dn",
+						},
+					},
+				}, idpv1alpha1.LDAPPhaseReady)
+				expectedMsg := fmt.Sprintf(
+					`successfully able to connect to "%s" and bind as user "%s" [validated with Secret "%s" at version "%s"]`,
+					env.SupervisorUpstreamLDAP.Host, env.SupervisorUpstreamLDAP.BindUsername,
+					secret.Name, secret.ResourceVersion,
+				)
+				requireSuccessfulLDAPIdentityProviderConditions(t, ldapIDP, expectedMsg)
+				return ldapIDP.Name
+			},
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
+				requestAuthorizationUsingCLIPasswordFlow(t,
+					downstreamAuthorizeURL,
+					env.SupervisorUpstreamLDAP.TestUserMailAttributeValue, // username to present to server during login
+					env.SupervisorUpstreamLDAP.TestUserPassword,           // password to present to server during login
+					httpClient,
+					false,
+				)
+			},
+			editRefreshSessionDataWithoutBreaking: func(t *testing.T, sessionData *psession.PinnipedSession, _, _ string) {
+				// even if we update this group to the wrong thing, we expect that it will return to the correct
+				// value after we refresh.
+				sessionData.Fosite.Claims.Extra["groups"] = []string{"some-wrong-group", "some-other-group"}
+			},
+			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)
+				fositeSessionData := pinnipedSession.Fosite
+				fositeSessionData.Claims.Subject = "not-right"
+			},
+			// the ID token Subject should be the Host URL plus the value pulled from the requested UserSearch.Attributes.UID attribute
+			wantDownstreamIDTokenSubjectToMatch: "^" + regexp.QuoteMeta(
+				"ldaps://"+env.SupervisorUpstreamLDAP.Host+
+					"?base="+url.QueryEscape(env.SupervisorUpstreamLDAP.UserSearchBase)+
+					"&sub="+base64.RawURLEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeValue)),
+			) + "$",
+			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$"
+			},
+			wantDownstreamIDTokenGroups: []string{},
+		},
 		{
 			name: "ldap with CN as username and group names as CNs and using an LDAP provider which only supports StartTLS", // try another variation of configuration options
 			maybeSkip: func(t *testing.T) {
@@ -1241,7 +1346,6 @@ func TestSupervisorLogin_Browser(t *testing.T) {
 				ctx, cancel := context.WithTimeout(context.Background(), 5*time.Minute)
 				defer cancel()
 
-				// Create the LDAPIdentityProvider using GenerateName to get a random name.
 				upstreams := client.IDPV1alpha1().LDAPIdentityProviders(env.SupervisorNamespace)
 				ldapIDP, err := upstreams.Get(ctx, idpName, metav1.GetOptions{})
 				require.NoError(t, err)
@@ -1263,6 +1367,87 @@ func TestSupervisorLogin_Browser(t *testing.T) {
 			},
 			wantDownstreamIDTokenGroups: env.SupervisorUpstreamLDAP.TestUserDirectGroupsDNs,
 		},
+		{
+			name: "ldap refresh updates groups to be empty after deleting the group search base",
+			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")
+				}
+			},
+			createIDP: func(t *testing.T) string {
+				t.Helper()
+
+				secret := testlib.CreateTestSecret(t, env.SupervisorNamespace, "ldap-service-account", v1.SecretTypeBasicAuth,
+					map[string]string{
+						v1.BasicAuthUsernameKey: env.SupervisorUpstreamLDAP.BindUsername,
+						v1.BasicAuthPasswordKey: env.SupervisorUpstreamLDAP.BindPassword,
+					},
+				)
+				secretName := secret.Name
+				ldapIDP := testlib.CreateTestLDAPIdentityProvider(t, idpv1alpha1.LDAPIdentityProviderSpec{
+					Host: env.SupervisorUpstreamLDAP.Host,
+					TLS: &idpv1alpha1.TLSSpec{
+						CertificateAuthorityData: base64.StdEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.CABundle)),
+					},
+					Bind: idpv1alpha1.LDAPIdentityProviderBind{
+						SecretName: secretName,
+					},
+					UserSearch: idpv1alpha1.LDAPIdentityProviderUserSearch{
+						Base:   env.SupervisorUpstreamLDAP.UserSearchBase,
+						Filter: "",
+						Attributes: idpv1alpha1.LDAPIdentityProviderUserSearchAttributes{
+							Username: env.SupervisorUpstreamLDAP.TestUserMailAttributeName,
+							UID:      env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeName,
+						},
+					},
+					GroupSearch: idpv1alpha1.LDAPIdentityProviderGroupSearch{
+						Base:   env.SupervisorUpstreamLDAP.GroupSearchBase,
+						Filter: "",
+						Attributes: idpv1alpha1.LDAPIdentityProviderGroupSearchAttributes{
+							GroupName: "dn",
+						},
+					},
+				}, idpv1alpha1.LDAPPhaseReady)
+				return ldapIDP.Name
+			},
+			requestAuthorization: func(t *testing.T, downstreamAuthorizeURL, _, _, _ string, httpClient *http.Client) {
+				requestAuthorizationUsingCLIPasswordFlow(t,
+					downstreamAuthorizeURL,
+					env.SupervisorUpstreamLDAP.TestUserMailAttributeValue, // username to present to server during login
+					env.SupervisorUpstreamLDAP.TestUserPassword,           // password to present to server during login
+					httpClient,
+					false,
+				)
+			},
+			editRefreshSessionDataWithoutBreaking: 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)
+				defer cancel()
+
+				upstreams := client.IDPV1alpha1().LDAPIdentityProviders(env.SupervisorNamespace)
+				ldapIDP, err := upstreams.Get(ctx, idpName, metav1.GetOptions{})
+				require.NoError(t, err)
+				ldapIDP.Spec.GroupSearch.Base = ""
+
+				_, err = upstreams.Update(ctx, ldapIDP, metav1.UpdateOptions{})
+				require.NoError(t, err)
+				time.Sleep(10 * time.Second) // wait for controllers to pick up the change
+			},
+			// the ID token Subject should be the Host URL plus the value pulled from the requested UserSearch.Attributes.UID attribute
+			wantDownstreamIDTokenSubjectToMatch: "^" + regexp.QuoteMeta(
+				"ldaps://"+env.SupervisorUpstreamLDAP.Host+
+					"?base="+url.QueryEscape(env.SupervisorUpstreamLDAP.UserSearchBase)+
+					"&sub="+base64.RawURLEncoding.EncodeToString([]byte(env.SupervisorUpstreamLDAP.TestUserUniqueIDAttributeValue)),
+			) + "$",
+			// the ID token Username should have been pulled from the requested UserSearch.Attributes.Username attribute
+			wantDownstreamIDTokenUsernameToMatch: func(_ string) string {
+				return "^" + regexp.QuoteMeta(env.SupervisorUpstreamLDAP.TestUserMailAttributeValue) + "$"
+			},
+			wantDownstreamIDTokenGroups:             env.SupervisorUpstreamLDAP.TestUserDirectGroupsDNs,
+			wantDownstreamIDTokenGroupsAfterRefresh: []string{},
+		},
 	}
 	for _, test := range tests {
 		tt := test
@@ -1272,12 +1457,14 @@ func TestSupervisorLogin_Browser(t *testing.T) {
 			testSupervisorLogin(t,
 				tt.createIDP,
 				tt.requestAuthorization,
+				tt.editRefreshSessionDataWithoutBreaking,
 				tt.breakRefreshSessionData,
 				tt.createTestUser,
 				tt.deleteTestUser,
 				tt.wantDownstreamIDTokenSubjectToMatch,
 				tt.wantDownstreamIDTokenUsernameToMatch,
 				tt.wantDownstreamIDTokenGroups,
+				tt.wantDownstreamIDTokenGroupsAfterRefresh,
 				tt.wantErrorDescription,
 				tt.wantErrorType,
 			)
@@ -1405,13 +1592,15 @@ func requireEventuallySuccessfulActiveDirectoryIdentityProviderConditions(t *tes
 func testSupervisorLogin(
 	t *testing.T,
 	createIDP func(t *testing.T) string,
-	requestAuthorization func(t *testing.T, downstreamAuthorizeURL, downstreamCallbackURL, username, password string, httpClient *http.Client),
+	requestAuthorization func(t *testing.T, downstreamAuthorizeURL string, downstreamCallbackURL string, username string, password string, httpClient *http.Client),
+	editRefreshSessionDataWithoutBreaking func(t *testing.T, pinnipedSession *psession.PinnipedSession, idpName, username string),
 	breakRefreshSessionData func(t *testing.T, pinnipedSession *psession.PinnipedSession, idpName, username string),
 	createTestUser func(t *testing.T) (string, string),
 	deleteTestUser func(t *testing.T, username string),
 	wantDownstreamIDTokenSubjectToMatch string,
 	wantDownstreamIDTokenUsernameToMatch func(username string) string,
 	wantDownstreamIDTokenGroups []string,
+	wantDownstreamIDTokenGroupsAfterRefresh []string,
 	wantErrorDescription string,
 	wantErrorType string,
 ) {
@@ -1565,6 +1754,28 @@ func testSupervisorLogin(
 		// token exchange on the original token
 		doTokenExchange(t, &downstreamOAuth2Config, tokenResponse, httpClient, discovery)
 
+		if editRefreshSessionDataWithoutBreaking != nil {
+			latestRefreshToken := tokenResponse.RefreshToken
+			signatureOfLatestRefreshToken := getFositeDataSignature(t, latestRefreshToken)
+
+			// First use the latest downstream refresh token to look up the corresponding session in the Supervisor's storage.
+			kubeClient := testlib.NewKubernetesClientset(t)
+			supervisorSecretsClient := kubeClient.CoreV1().Secrets(env.SupervisorNamespace)
+			oauthStore := oidc.NewKubeStorage(supervisorSecretsClient, oidc.DefaultOIDCTimeoutsConfiguration())
+			storedRefreshSession, err := oauthStore.GetRefreshTokenSession(ctx, signatureOfLatestRefreshToken, nil)
+			require.NoError(t, err)
+
+			// 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")
+
+			editRefreshSessionDataWithoutBreaking(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.
+			require.NoError(t, oauthStore.DeleteRefreshTokenSession(ctx, signatureOfLatestRefreshToken))
+			require.NoError(t, oauthStore.CreateRefreshTokenSession(ctx, signatureOfLatestRefreshToken, storedRefreshSession))
+		}
 		// Use the refresh token to get new tokens
 		refreshSource := downstreamOAuth2Config.TokenSource(oidcHTTPClientContext, &oauth2.Token{RefreshToken: tokenResponse.RefreshToken})
 		refreshedTokenResponse, err := refreshSource.Token()
@@ -1572,9 +1783,12 @@ func testSupervisorLogin(
 
 		// When refreshing, expect to get an "at_hash" claim, but no "nonce" claim.
 		expectRefreshedIDTokenClaims := []string{"iss", "exp", "sub", "aud", "auth_time", "iat", "jti", "rat", "username", "groups", "at_hash"}
+		if wantDownstreamIDTokenGroupsAfterRefresh == nil {
+			wantDownstreamIDTokenGroupsAfterRefresh = wantDownstreamIDTokenGroups
+		}
 		verifyTokenResponse(t,
 			refreshedTokenResponse, discovery, downstreamOAuth2Config, "",
-			expectRefreshedIDTokenClaims, wantDownstreamIDTokenSubjectToMatch, wantDownstreamIDTokenUsernameToMatch(username), wantDownstreamIDTokenGroups)
+			expectRefreshedIDTokenClaims, wantDownstreamIDTokenSubjectToMatch, wantDownstreamIDTokenUsernameToMatch(username), wantDownstreamIDTokenGroupsAfterRefresh)
 
 		require.NotEqual(t, tokenResponse.AccessToken, refreshedTokenResponse.AccessToken)
 		require.NotEqual(t, tokenResponse.RefreshToken, refreshedTokenResponse.RefreshToken)