Merge pull request #168 from mattmoyer/cli-session-refresh

Add support for refresh token flow in OIDC CLI client.

internal/oidcclient/login.go

@@ -30,6 +30,10 @@ const (
 	// This is non-zero to ensure that most of the time, your ID token won't expire in the middle of a multi-step k8s
 	// API operation.
 	minIDTokenValidity = 10 * time.Minute
+
+	// 	refreshTimeout is the amount of time allotted for OAuth2 refresh operations. Since these don't involve any
+	// 	user interaction, they should always be roughly as fast as network latency.
+	refreshTimeout = 30 * time.Second
 )
 
 type handlerState struct {
@@ -56,6 +60,7 @@ type handlerState struct {
 	generatePKCE  func() (pkce.Code, error)
 	generateNonce func() (nonce.Nonce, error)
 	openURL       func(string) error
+	oidcDiscover  func(context.Context, string) (discoveryI, error)
 
 	callbacks chan callbackResult
 }
@@ -123,6 +128,11 @@ type nopCache struct{}
 func (*nopCache) GetToken(SessionCacheKey) *Token  { return nil }
 func (*nopCache) PutToken(SessionCacheKey, *Token) {}
 
+type discoveryI interface {
+	Endpoint() oauth2.Endpoint
+	Verifier(*oidc.Config) *oidc.IDTokenVerifier
+}
+
 // Login performs an OAuth2/OIDC authorization code login using a localhost listener.
 func Login(issuer string, clientID string, opts ...Option) (*Token, error) {
 	h := handlerState{
@@ -140,6 +150,9 @@ func Login(issuer string, clientID string, opts ...Option) (*Token, error) {
 		generateNonce: nonce.Generate,
 		generatePKCE:  pkce.Generate,
 		openURL:       browser.OpenURL,
+		oidcDiscover: func(ctx context.Context, iss string) (discoveryI, error) {
+			return oidc.NewProvider(ctx, iss)
+		},
 	}
 	for _, opt := range opts {
 		if err := opt(&h); err != nil {
@@ -177,52 +190,52 @@ func Login(issuer string, clientID string, opts ...Option) (*Token, error) {
 	}
 
 	// If the ID token is still valid for a bit, return it immediately and skip the rest of the flow.
-	if cached := h.cache.GetToken(cacheKey); cached != nil &&
+	cached := h.cache.GetToken(cacheKey)
-		cached.IDToken != nil &&
+	if cached != nil && cached.IDToken != nil && time.Until(cached.IDToken.Expiry.Time) > minIDTokenValidity {
-		time.Until(cached.IDToken.Expiry.Time) > minIDTokenValidity {
 		return cached, nil
 	}
 
 	// Perform OIDC discovery.
-	provider, err := oidc.NewProvider(h.ctx, h.issuer)
+	discovered, err := h.oidcDiscover(h.ctx, h.issuer)
 	if err != nil {
 		return nil, fmt.Errorf("could not perform OIDC discovery for %q: %w", h.issuer, err)
 	}
-	h.idTokenVerifier = provider.Verifier(&oidc.Config{ClientID: h.clientID})
+	h.idTokenVerifier = discovered.Verifier(&oidc.Config{ClientID: h.clientID})
-
-	// Open a TCP listener.
-	listener, err := net.Listen("tcp", h.listenAddr)
-	if err != nil {
-		return nil, fmt.Errorf("could not open callback listener: %w", err)
-	}
 
 	// Build an OAuth2 configuration based on the OIDC discovery data and our callback endpoint.
 	h.oauth2Config = &oauth2.Config{
 		ClientID: h.clientID,
-		Endpoint: provider.Endpoint(),
+		Endpoint: discovered.Endpoint(),
-		RedirectURL: (&url.URL{
-			Scheme: "http",
-			Host:   listener.Addr().String(),
-			Path:   h.callbackPath,
-		}).String(),
 		Scopes:   h.scopes,
 	}
 
-	// Start a callback server in a background goroutine.
+	// If there was a cached refresh token, attempt to use the refresh flow instead of a fresh login.
-	mux := http.NewServeMux()
+	if cached != nil && cached.RefreshToken != nil && cached.RefreshToken.Token != "" {
-	mux.Handle(h.callbackPath, httperr.HandlerFunc(h.handleAuthCodeCallback))
+		freshToken, err := h.handleRefresh(ctx, cached.RefreshToken)
-	srv := http.Server{
+		if err != nil {
-		Handler:     securityheader.Wrap(mux),
+			return nil, err
-		BaseContext: func(_ net.Listener) context.Context { return h.ctx },
 		}
-	go func() { _ = srv.Serve(listener) }()
+		// If we got a fresh token, we can update the cache and return it. Otherwise we fall through to the full refresh flow.
-	defer func() {
+		if freshToken != nil {
-		// Gracefully shut down the server, allowing up to 5 seconds for
+			h.cache.PutToken(cacheKey, freshToken)
-		// clients to receive any in-flight responses.
+			return freshToken, nil
-		shutdownCtx, cancel := context.WithTimeout(h.ctx, 1*time.Second)
+		}
-		_ = srv.Shutdown(shutdownCtx)
+	}
-		cancel()
+
-	}()
+	// Open a TCP listener and update the OAuth2 redirect_uri to match (in case we are using an ephemeral port number).
+	listener, err := net.Listen("tcp", h.listenAddr)
+	if err != nil {
+		return nil, fmt.Errorf("could not open callback listener: %w", err)
+	}
+	h.oauth2Config.RedirectURL = (&url.URL{
+		Scheme: "http",
+		Host:   listener.Addr().String(),
+		Path:   h.callbackPath,
+	}).String()
+
+	// Start a callback server in a background goroutine.
+	shutdown := h.serve(listener)
+	defer shutdown()
 
 	// Open the authorize URL in the users browser.
 	authorizeURL := h.oauth2Config.AuthCodeURL(
@@ -249,6 +262,22 @@ func Login(issuer string, clientID string, opts ...Option) (*Token, error) {
 	}
 }
 
+func (h *handlerState) handleRefresh(ctx context.Context, refreshToken *RefreshToken) (*Token, error) {
+	ctx, cancel := context.WithTimeout(ctx, refreshTimeout)
+	defer cancel()
+	refreshSource := h.oauth2Config.TokenSource(ctx, &oauth2.Token{RefreshToken: refreshToken.Token})
+
+	refreshed, err := refreshSource.Token()
+	if err != nil {
+		// Ignore errors during refresh, but return nil which will trigger the full login flow.
+		return nil, nil
+	}
+
+	// The spec is not 100% clear about whether an ID token from the refresh flow should include a nonce, and at least
+	// some providers do not include one, so we skip the nonce validation here (but not other validations).
+	return h.validateToken(ctx, refreshed, false)
+}
+
 func (h *handlerState) handleAuthCodeCallback(w http.ResponseWriter, r *http.Request) (err error) {
 	// If we return an error, also report it back over the channel to the main CLI thread.
 	defer func() {
@@ -280,37 +309,64 @@ func (h *handlerState) handleAuthCodeCallback(w http.ResponseWriter, r *http.Req
 	}
 
 	// Perform required validations on the returned ID token.
-	idTok, hasIDTok := oauth2Tok.Extra("id_token").(string)
+	token, err := h.validateToken(r.Context(), oauth2Tok, true)
-	if !hasIDTok {
-		return httperr.New(http.StatusBadRequest, "received response missing ID token")
-	}
-	validated, err := h.idTokenVerifier.Verify(r.Context(), idTok)
 	if err != nil {
-		return httperr.Wrap(http.StatusBadRequest, "received invalid ID token", err)
+		return err
-	}
-	if validated.AccessTokenHash != "" {
-		if err := validated.VerifyAccessToken(oauth2Tok.AccessToken); err != nil {
-			return httperr.Wrap(http.StatusBadRequest, "received invalid ID token", err)
-		}
-	}
-	if err := h.nonce.Validate(validated); err != nil {
-		return httperr.Wrap(http.StatusBadRequest, "received ID token with invalid nonce", err)
 	}
 
-	h.callbacks <- callbackResult{token: &Token{
+	h.callbacks <- callbackResult{token: token}
+	_, _ = w.Write([]byte("you have been logged in and may now close this tab"))
+	return nil
+}
+
+func (h *handlerState) validateToken(ctx context.Context, tok *oauth2.Token, checkNonce bool) (*Token, error) {
+	idTok, hasIDTok := tok.Extra("id_token").(string)
+	if !hasIDTok {
+		return nil, httperr.New(http.StatusBadRequest, "received response missing ID token")
+	}
+	validated, err := h.idTokenVerifier.Verify(ctx, idTok)
+	if err != nil {
+		return nil, httperr.Wrap(http.StatusBadRequest, "received invalid ID token", err)
+	}
+	if validated.AccessTokenHash != "" {
+		if err := validated.VerifyAccessToken(tok.AccessToken); err != nil {
+			return nil, httperr.Wrap(http.StatusBadRequest, "received invalid ID token", err)
+		}
+	}
+	if checkNonce {
+		if err := h.nonce.Validate(validated); err != nil {
+			return nil, httperr.Wrap(http.StatusBadRequest, "received ID token with invalid nonce", err)
+		}
+	}
+	return &Token{
 		AccessToken: &AccessToken{
-			Token:  oauth2Tok.AccessToken,
+			Token:  tok.AccessToken,
-			Type:   oauth2Tok.TokenType,
+			Type:   tok.TokenType,
-			Expiry: metav1.NewTime(oauth2Tok.Expiry),
+			Expiry: metav1.NewTime(tok.Expiry),
 		},
 		RefreshToken: &RefreshToken{
-			Token: oauth2Tok.RefreshToken,
+			Token: tok.RefreshToken,
 		},
 		IDToken: &IDToken{
 			Token:  idTok,
 			Expiry: metav1.NewTime(validated.Expiry),
 		},
-	}}
+	}, nil
-	_, _ = w.Write([]byte("you have been logged in and may now close this tab"))
+}
-	return nil
+
+func (h *handlerState) serve(listener net.Listener) func() {
+	mux := http.NewServeMux()
+	mux.Handle(h.callbackPath, httperr.HandlerFunc(h.handleAuthCodeCallback))
+	srv := http.Server{
+		Handler:     securityheader.Wrap(mux),
+		BaseContext: func(_ net.Listener) context.Context { return h.ctx },
+	}
+	go func() { _ = srv.Serve(listener) }()
+	return func() {
+		// Gracefully shut down the server, allowing up to 5 seconds for
+		// clients to receive any in-flight responses.
+		shutdownCtx, cancel := context.WithTimeout(h.ctx, 1*time.Second)
+		_ = srv.Shutdown(shutdownCtx)
+		cancel()
+	}
 }

internal/oidcclient/login_test.go

@@ -15,6 +15,7 @@ import (
 
 	"github.com/coreos/go-oidc"
 	"github.com/golang/mock/gomock"
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"golang.org/x/oauth2"
 	"gopkg.in/square/go-jose.v2"
@@ -49,7 +50,10 @@ func (m *mockSessionCache) PutToken(key SessionCacheKey, token *Token) {
 }
 
 func TestLogin(t *testing.T) {
-	time1 := time.Date(3020, 10, 12, 13, 14, 15, 16, time.UTC)
+	time1 := time.Date(2035, 10, 12, 13, 14, 15, 16, time.UTC)
+	time1Unix := int64(2075807775)
+	require.Equal(t, time1Unix, time1.Add(2*time.Minute).Unix())
+
 	testToken := Token{
 		AccessToken: &AccessToken{
 			Token:  "test-access-token",
@@ -59,7 +63,9 @@ func TestLogin(t *testing.T) {
 			Token: "test-refresh-token",
 		},
 		IDToken: &IDToken{
-			Token:  "test-id-token",
+			// Test JWT generated with https://smallstep.com/docs/cli/crypto/jwt/ (using time1Unix from above):
+			// step crypto keypair key.pub key.priv --kty RSA --no-password --insecure --force && echo '{}' | step crypto jwt sign --key key.priv --aud test-client-id --sub test-user --subtle --kid="test-kid" --jti="test-jti" --exp 2075807775
+			Token:  "eyJhbGciOiJSUzI1NiIsImtpZCI6InRlc3Qta2lkIiwidHlwIjoiSldUIn0.eyJhdWQiOiJ0ZXN0LWNsaWVudC1pZCIsImV4cCI6MjA3NTgwNzc3NSwiaWF0IjoxNjAzMzk5NTY4LCJpc3MiOiJ0ZXN0LWlzc3VlciIsImp0aSI6InRlc3QtanRpIiwibmJmIjoxNjAzMzk5NTY4LCJzdWIiOiJ0ZXN0LXVzZXIifQ.CdwUWQb6xELeFlC4u84K4rzks7YiDJiXxIo_SaRvCHBijxtil812RBRfPuAyYKJlGwFx1g-JYvkUg69X5NmvmLXkaOdHIKUAT7Nqa7yqd1xOAP9IlFj9qZM3Q7s8gWWW9da-_ryagzN4fyGfNfYeGhzIriSMaVpuBGz1eg6f-6VuuulnoiOpl8A0l50u0MdRjjsxRHuiR2loIhUxoIQQ9xN8w53UiP0R1uz8_uV0_K93RSq37aPjsnCXRLwUUb3azkRVe6B9EUW1ihthQ-KfRaU1iq2rY1m5UqNzf0NqDXCrN5SF-GVxOhKXJTsN4-PABfJBjqxg6dGUGeIa2JhFcA",
 			Expiry: metav1.NewTime(time1.Add(2 * time.Minute)),
 		},
 	}
@@ -70,11 +76,15 @@ func TestLogin(t *testing.T) {
 	}))
 	t.Cleanup(errorServer.Close)
 
-	// Start a test server that returns a real keyset
+	// Start a test server that returns a real keyset and answers refresh requests.
 	providerMux := http.NewServeMux()
 	successServer := httptest.NewServer(providerMux)
 	t.Cleanup(successServer.Close)
 	providerMux.HandleFunc("/.well-known/openid-configuration", func(w http.ResponseWriter, r *http.Request) {
+		if r.Method != http.MethodGet {
+			http.Error(w, "unexpected method", http.StatusMethodNotAllowed)
+			return
+		}
 		w.Header().Set("content-type", "application/json")
 		type providerJSON struct {
 			Issuer   string `json:"issuer"`
@@ -89,6 +99,44 @@ func TestLogin(t *testing.T) {
 			JWKSURL:  successServer.URL + "/keys",
 		})
 	})
+	providerMux.HandleFunc("/token", func(w http.ResponseWriter, r *http.Request) {
+		if r.Method != http.MethodPost {
+			http.Error(w, "unexpected method", http.StatusMethodNotAllowed)
+			return
+		}
+		if err := r.ParseForm(); err != nil {
+			http.Error(w, err.Error(), http.StatusBadRequest)
+			return
+		}
+		if r.Form.Get("client_id") != "test-client-id" {
+			http.Error(w, "expected client_id 'test-client-id'", http.StatusBadRequest)
+			return
+		}
+		if r.Form.Get("grant_type") != "refresh_token" {
+			http.Error(w, "expected refresh_token grant type", http.StatusBadRequest)
+			return
+		}
+
+		var response struct {
+			oauth2.Token
+			IDToken   string `json:"id_token,omitempty"`
+			ExpiresIn int64  `json:"expires_in"`
+		}
+		response.AccessToken = testToken.AccessToken.Token
+		response.ExpiresIn = int64(time.Until(testToken.AccessToken.Expiry.Time).Seconds())
+		response.RefreshToken = testToken.RefreshToken.Token
+		response.IDToken = testToken.IDToken.Token
+
+		if r.Form.Get("refresh_token") == "test-refresh-token-returning-invalid-id-token" {
+			response.IDToken = "not a valid JWT"
+		} else if r.Form.Get("refresh_token") != "test-refresh-token" {
+			http.Error(w, "expected refresh_token to be 'test-refresh-token'", http.StatusBadRequest)
+			return
+		}
+
+		w.Header().Set("content-type", "application/json")
+		require.NoError(t, json.NewEncoder(w).Encode(&response))
+	})
 
 	tests := []struct {
 		name      string
@@ -192,6 +240,106 @@ func TestLogin(t *testing.T) {
 			issuer:  errorServer.URL,
 			wantErr: fmt.Sprintf("could not perform OIDC discovery for %q: 500 Internal Server Error: some discovery error\n", errorServer.URL),
 		},
+		{
+			name:     "session cache hit with refreshable token",
+			issuer:   successServer.URL,
+			clientID: "test-client-id",
+			opt: func(t *testing.T) Option {
+				return func(h *handlerState) error {
+					cache := &mockSessionCache{t: t, getReturnsToken: &Token{
+						IDToken: &IDToken{
+							Token:  "expired-test-id-token",
+							Expiry: metav1.Now(), // less than Now() + minIDTokenValidity
+						},
+						RefreshToken: &RefreshToken{Token: "test-refresh-token"},
+					}}
+					t.Cleanup(func() {
+						cacheKey := SessionCacheKey{
+							Issuer:      successServer.URL,
+							ClientID:    "test-client-id",
+							Scopes:      []string{"test-scope"},
+							RedirectURI: "http://localhost:0/callback",
+						}
+						require.Equal(t, []SessionCacheKey{cacheKey}, cache.sawGetKeys)
+						require.Equal(t, []SessionCacheKey{cacheKey}, cache.sawPutKeys)
+						require.Len(t, cache.sawPutTokens, 1)
+						require.Equal(t, testToken.IDToken.Token, cache.sawPutTokens[0].IDToken.Token)
+					})
+					h.cache = cache
+
+					h.oidcDiscover = func(ctx context.Context, iss string) (discoveryI, error) {
+						provider, err := oidc.NewProvider(ctx, iss)
+						require.NoError(t, err)
+						return &mockDiscovery{provider: provider}, nil
+					}
+					return nil
+				}
+			},
+			wantToken: &testToken,
+		},
+		{
+			name:     "session cache hit but refresh returns invalid token",
+			issuer:   successServer.URL,
+			clientID: "test-client-id",
+			opt: func(t *testing.T) Option {
+				return func(h *handlerState) error {
+					cache := &mockSessionCache{t: t, getReturnsToken: &Token{
+						IDToken: &IDToken{
+							Token:  "expired-test-id-token",
+							Expiry: metav1.Now(), // less than Now() + minIDTokenValidity
+						},
+						RefreshToken: &RefreshToken{Token: "test-refresh-token-returning-invalid-id-token"},
+					}}
+					t.Cleanup(func() {
+						require.Empty(t, cache.sawPutKeys)
+						require.Empty(t, cache.sawPutTokens)
+					})
+					h.cache = cache
+
+					h.oidcDiscover = func(ctx context.Context, iss string) (discoveryI, error) {
+						provider, err := oidc.NewProvider(ctx, iss)
+						require.NoError(t, err)
+						return &mockDiscovery{provider: provider}, nil
+					}
+
+					return nil
+				}
+			},
+			wantErr: "received invalid ID token: oidc: malformed jwt: square/go-jose: compact JWS format must have three parts",
+		},
+		{
+			name:     "session cache hit but refresh fails",
+			issuer:   successServer.URL,
+			clientID: "not-the-test-client-id",
+			opt: func(t *testing.T) Option {
+				return func(h *handlerState) error {
+					cache := &mockSessionCache{t: t, getReturnsToken: &Token{
+						IDToken: &IDToken{
+							Token:  "expired-test-id-token",
+							Expiry: metav1.Now(), // less than Now() + minIDTokenValidity
+						},
+						RefreshToken: &RefreshToken{Token: "test-refresh-token"},
+					}}
+					t.Cleanup(func() {
+						require.Empty(t, cache.sawPutKeys)
+						require.Empty(t, cache.sawPutTokens)
+					})
+					h.cache = cache
+
+					h.oidcDiscover = func(ctx context.Context, iss string) (discoveryI, error) {
+						provider, err := oidc.NewProvider(ctx, iss)
+						require.NoError(t, err)
+						return &mockDiscovery{provider: provider}, nil
+					}
+
+					h.listenAddr = "invalid-listen-address"
+
+					return nil
+				}
+			},
+			// Expect this to fall through to the authorization code flow, so it fails here.
+			wantErr: "could not open callback listener: listen tcp: address invalid-listen-address: missing port in address",
+		},
 		{
 			name: "listen failure",
 			opt: func(t *testing.T) Option {
@@ -320,7 +468,30 @@ func TestLogin(t *testing.T) {
 				require.Nil(t, tok)
 				return
 			}
-			require.Equal(t, tt.wantToken, tok)
+			require.NoError(t, err)
+
+			if tt.wantToken == nil {
+				require.Nil(t, tok)
+				return
+			}
+			require.NotNil(t, tok)
+
+			if want := tt.wantToken.AccessToken; want != nil {
+				require.NotNil(t, tok.AccessToken)
+				require.Equal(t, want.Token, tok.AccessToken.Token)
+				require.Equal(t, want.Type, tok.AccessToken.Type)
+				requireTimeInDelta(t, want.Expiry.Time, tok.AccessToken.Expiry.Time, 5*time.Second)
+			} else {
+				assert.Nil(t, tok.AccessToken)
+			}
+			require.Equal(t, tt.wantToken.RefreshToken, tok.RefreshToken)
+			if want := tt.wantToken.IDToken; want != nil {
+				require.NotNil(t, tok.IDToken)
+				require.Equal(t, want.Token, tok.IDToken.Token)
+				requireTimeInDelta(t, want.Expiry.Time, tok.IDToken.Expiry.Time, 5*time.Second)
+			} else {
+				assert.Nil(t, tok.IDToken)
+			}
 		})
 	}
 }
@@ -504,3 +675,22 @@ func mockVerifier() *oidc.IDTokenVerifier {
 		SkipClientIDCheck: true,
 	})
 }
+
+type mockDiscovery struct{ provider *oidc.Provider }
+
+func (m *mockDiscovery) Endpoint() oauth2.Endpoint { return m.provider.Endpoint() }
+
+func (m *mockDiscovery) Verifier(config *oidc.Config) *oidc.IDTokenVerifier { return mockVerifier() }
+
+func requireTimeInDelta(t *testing.T, t1 time.Time, t2 time.Time, delta time.Duration) {
+	require.InDeltaf(t,
+		float64(t1.UnixNano()),
+		float64(t2.UnixNano()),
+		float64(delta.Nanoseconds()),
+		"expected %s and %s to be < %s apart, but they are %s apart",
+		t1.Format(time.RFC3339Nano),
+		t2.Format(time.RFC3339Nano),
+		delta.String(),
+		t1.Sub(t2).String(),
+	)
+}

test/integration/cli_test.go

@@ -26,6 +26,8 @@ import (
 	"gopkg.in/square/go-jose.v2"
 	clientauthenticationv1beta1 "k8s.io/client-go/pkg/apis/clientauthentication/v1beta1"
 
+	"go.pinniped.dev/internal/oidcclient"
+	"go.pinniped.dev/internal/oidcclient/filesession"
 	"go.pinniped.dev/test/library"
 )
 
@@ -176,18 +178,12 @@ func TestCLILoginOIDC(t *testing.T) {
 	sessionCachePath := t.TempDir() + "/sessions.yaml"
 
 	// Start the CLI running the "alpha login oidc [...]" command with stdout/stderr connected to pipes.
-	t.Logf("starting CLI subprocess")
+	cmd := oidcLoginCommand(ctx, t, pinnipedExe, sessionCachePath)
-	cmd := exec.CommandContext(ctx, pinnipedExe, "alpha", "login", "oidc",
-		"--issuer", env.OIDCUpstream.Issuer,
-		"--client-id", env.OIDCUpstream.ClientID,
-		"--listen-port", strconv.Itoa(env.OIDCUpstream.LocalhostPort),
-		"--session-cache", sessionCachePath,
-		"--skip-browser",
-	)
 	stderr, err := cmd.StderrPipe()
 	require.NoError(t, err)
 	stdout, err := cmd.StdoutPipe()
 	require.NoError(t, err)
+	t.Logf("starting CLI subprocess")
 	require.NoError(t, cmd.Start())
 	t.Cleanup(func() {
 		err := cmd.Wait()
@@ -312,23 +308,44 @@ func TestCLILoginOIDC(t *testing.T) {
 
 	// Run the CLI again with the same session cache and login parameters.
 	t.Logf("starting second CLI subprocess to test session caching")
-	secondCtx, secondCancel := context.WithTimeout(ctx, 5*time.Second)
+	cmd2Output, err := oidcLoginCommand(ctx, t, pinnipedExe, sessionCachePath).CombinedOutput()
-	defer secondCancel()
+	require.NoError(t, err, string(cmd2Output))
-	cmdOutput, err := exec.CommandContext(secondCtx, pinnipedExe, "alpha", "login", "oidc",
-		"--issuer", env.OIDCUpstream.Issuer,
-		"--client-id", env.OIDCUpstream.ClientID,
-		"--listen-port", strconv.Itoa(env.OIDCUpstream.LocalhostPort),
-		"--session-cache", sessionCachePath,
-		"--skip-browser",
-	).CombinedOutput()
-	require.NoError(t, err)
 
 	// Expect the CLI to output the same ExecCredential in JSON format.
 	t.Logf("validating second ExecCredential")
 	var credOutput2 clientauthenticationv1beta1.ExecCredential
-	require.NoErrorf(t, json.Unmarshal(cmdOutput, &credOutput2),
+	require.NoErrorf(t, json.Unmarshal(cmd2Output, &credOutput2),
-		"command returned something other than an ExecCredential:\n%s", string(cmdOutput))
+		"command returned something other than an ExecCredential:\n%s", string(cmd2Output))
 	require.Equal(t, credOutput, credOutput2)
+
+	// Overwrite the cache entry to remove the access and ID tokens.
+	t.Logf("overwriting cache to remove valid ID token")
+	cache := filesession.New(sessionCachePath)
+	cacheKey := oidcclient.SessionCacheKey{
+		Issuer:      env.OIDCUpstream.Issuer,
+		ClientID:    env.OIDCUpstream.ClientID,
+		Scopes:      []string{"email", "offline_access", "openid", "profile"},
+		RedirectURI: fmt.Sprintf("http://localhost:%d/callback", env.OIDCUpstream.LocalhostPort),
+	}
+	cached := cache.GetToken(cacheKey)
+	require.NotNil(t, cached)
+	require.NotNil(t, cached.RefreshToken)
+	require.NotEmpty(t, cached.RefreshToken.Token)
+	cached.IDToken = nil
+	cached.AccessToken = nil
+	cache.PutToken(cacheKey, cached)
+
+	// Run the CLI a third time with the same session cache and login parameters.
+	t.Logf("starting third CLI subprocess to test refresh flow")
+	cmd3Output, err := oidcLoginCommand(ctx, t, pinnipedExe, sessionCachePath).CombinedOutput()
+	require.NoError(t, err, string(cmd2Output))
+
+	// Expect the CLI to output a new ExecCredential in JSON format (different from the one returned the first two times).
+	t.Logf("validating third ExecCredential")
+	var credOutput3 clientauthenticationv1beta1.ExecCredential
+	require.NoErrorf(t, json.Unmarshal(cmd3Output, &credOutput3),
+		"command returned something other than an ExecCredential:\n%s", string(cmd2Output))
+	require.NotEqual(t, credOutput2.Status.Token, credOutput3.Status.Token)
 }
 
 func waitForVisibleElements(t *testing.T, page *agouti.Page, selectors ...string) {
@@ -375,3 +392,14 @@ func spawnTestGoroutine(t *testing.T, f func() error) {
 	})
 	eg.Go(f)
 }
+
+func oidcLoginCommand(ctx context.Context, t *testing.T, pinnipedExe string, sessionCachePath string) *exec.Cmd {
+	env := library.IntegrationEnv(t)
+	return exec.CommandContext(ctx, pinnipedExe, "alpha", "login", "oidc",
+		"--issuer", env.OIDCUpstream.Issuer,
+		"--client-id", env.OIDCUpstream.ClientID,
+		"--listen-port", strconv.Itoa(env.OIDCUpstream.LocalhostPort),
+		"--session-cache", sessionCachePath,
+		"--skip-browser",
+	)
+}