Provide error suggestions for AADSTS530084 and include auth error details when emitted as ErrorWithSuggestion in telemetry

cli/azd/cmd/auth_login.go

@@ -314,10 +314,12 @@ func (la *loginAction) Run(ctx context.Context) (*actions.ActionResult, error) {
 		// We print any non-setup related errors to stderr.
 		// We always return a zero exit code.
 		token, err := la.verifyLoggedIn(ctx)
-		_, loginExpiryError := errors.AsType[*auth.ReLoginRequiredError](err)
+		// An *internal.ErrorWithSuggestion already carries actionable, user-facing guidance
+		// surfaced through the login result; avoid double-printing the raw error.
+		_, hasSuggestion := errors.AsType[*internal.ErrorWithSuggestion](err)
 		if err != nil &&
 			!errors.Is(err, auth.ErrNoCurrentUser) &&
-			!loginExpiryError {
+			!hasSuggestion {
 			fmt.Fprintln(la.console.Handles().Stderr, err.Error())
 		}
 

cli/azd/cmd/auth_status.go

@@ -81,10 +81,12 @@ func (a *authStatusAction) Run(ctx context.Context) (*actions.ActionResult, erro
 
 	// get user account information
 	details, err := a.authManager.LogInDetails(ctx)
-	_, loginExpiryError := errors.AsType[*auth.ReLoginRequiredError](err)
+	// An *internal.ErrorWithSuggestion already carries actionable, user-facing guidance
+	// surfaced through the status result; avoid double-printing the raw error.
+	_, hasSuggestion := errors.AsType[*internal.ErrorWithSuggestion](err)
 	if err != nil {
 		if !errors.Is(err, auth.ErrNoCurrentUser) &&
-			!loginExpiryError {
+			!hasSuggestion {
 			// print a useful message for unknown errors
 			fmt.Fprintln(a.console.Handles().Stderr, err.Error())
 		}

cli/azd/internal/cmd/errors.go

@@ -52,7 +52,11 @@ func MapError(err error, span tracing.Span) {
 		errDetails = append(errDetails, fields.ErrCategory.String("auth"))
 	} else if errWithSuggestion, ok := errors.AsType[*internal.ErrorWithSuggestion](err); ok {
 		errCode = "error.suggestion"
-		span.SetAttributes(fields.ErrType.String(classifySuggestionType(errWithSuggestion.Unwrap())))
+		innerErr := errWithSuggestion.Unwrap()
+		span.SetAttributes(fields.ErrType.String(classifySuggestionType(innerErr)))
+		if authFailedErr, ok := errors.AsType[*auth.AuthFailedError](innerErr); ok {
+			errDetails = append(errDetails, authFailedTelemetryDetails(authFailedErr)...)
+		}
 	} else if respErr, ok := errors.AsType[*azcore.ResponseError](err); ok {
 		serviceName := "other"
 		statusCode := -1
@@ -173,18 +177,7 @@ func MapError(err error, span tracing.Span) {
 			errDetails = append(errDetails, fields.ToolName.String(strings.Join(toolCheckErr.ToolNames, ",")))
 		}
 	} else if authFailedErr, ok := errors.AsType[*auth.AuthFailedError](err); ok {
-		errDetails = append(errDetails, fields.ServiceName.String("aad"))
-		if authFailedErr.Parsed != nil {
-			codes := make([]string, 0, len(authFailedErr.Parsed.ErrorCodes))
-			for _, code := range authFailedErr.Parsed.ErrorCodes {
-				codes = append(codes, fmt.Sprintf("%d", code))
-			}
-			serviceErr := strings.Join(codes, ",")
-			errDetails = append(errDetails,
-				fields.ServiceStatusCode.String(authFailedErr.Parsed.Error),
-				fields.ServiceErrorCode.String(serviceErr),
-				fields.ServiceCorrelationId.String(authFailedErr.Parsed.CorrelationId))
-		}
+		errDetails = append(errDetails, authFailedTelemetryDetails(authFailedErr)...)
 		errCode = "service.aad.failed"
 	} else if errors.Is(err, auth.ErrNoCurrentUser) {
 		errCode = "auth.not_logged_in"
@@ -216,6 +209,24 @@ func MapError(err error, span tracing.Span) {
 	span.SetStatus(codes.Error, errCode)
 }
 
+func authFailedTelemetryDetails(authFailedErr *auth.AuthFailedError) []attribute.KeyValue {
+	errDetails := []attribute.KeyValue{fields.ServiceName.String("aad")}
+	if authFailedErr == nil || authFailedErr.Parsed == nil {
+		return errDetails
+	}
+
+	codes := make([]string, 0, len(authFailedErr.Parsed.ErrorCodes))
+	for _, code := range authFailedErr.Parsed.ErrorCodes {
+		codes = append(codes, fmt.Sprintf("%d", code))
+	}
+
+	return append(errDetails,
+		fields.ServiceStatusCode.String(authFailedErr.Parsed.Error),
+		fields.ServiceErrorCode.String(strings.Join(codes, ",")),
+		fields.ServiceCorrelationId.String(authFailedErr.Parsed.CorrelationId),
+	)
+}
+
 // classifySentinel checks if the error matches a known sentinel
 // and returns the corresponding telemetry code, or "" if no match.
 func classifySentinel(err error) string {

cli/azd/internal/cmd/errors_test.go

@@ -211,6 +211,28 @@ func Test_MapError(t *testing.T) {
 				fields.ErrorKey(fields.ErrCategory.Key).String("auth"),
 			},
 		},
+		{
+			name: "WithTokenProtectionBlockedAuthFailedError",
+			err: &internal.ErrorWithSuggestion{
+				Err: &auth.AuthFailedError{
+					Parsed: &auth.AadErrorResponse{
+						Error:         "invalid_grant",
+						ErrorCodes:    []int{530084},
+						CorrelationId: "blocked-token-protection",
+					},
+				},
+			},
+			// AADSTS530084 surfaced via the suggestion wrapper still classifies as the generic
+			// AAD service failure for telemetry, and should preserve the wrapped AAD details.
+			wantErrReason: "error.suggestion",
+			wantErrDetails: []attribute.KeyValue{
+				fields.ErrType.String("service.aad.failed"),
+				fields.ErrorKey(fields.ServiceName.Key).String("aad"),
+				fields.ErrorKey(fields.ServiceErrorCode.Key).String("530084"),
+				fields.ErrorKey(fields.ServiceStatusCode.Key).String("invalid_grant"),
+				fields.ErrorKey(fields.ServiceCorrelationId.Key).String("blocked-token-protection"),
+			},
+		},
 		{
 			name:          "WithAzidentityAuthenticationFailedError",
 			err:           &azidentity.AuthenticationFailedError{},

cli/azd/internal/grpcserver/server.go

@@ -15,6 +15,7 @@ import (
 	"github.com/azure/azure-dev/cli/azd/pkg/auth"
 	"github.com/azure/azure-dev/cli/azd/pkg/azdext"
 	"github.com/azure/azure-dev/cli/azd/pkg/extensions"
+	"google.golang.org/genproto/googleapis/rpc/errdetails"
 	"google.golang.org/grpc"
 	"google.golang.org/grpc/codes"
 	"google.golang.org/grpc/metadata"
@@ -268,31 +269,84 @@ func (s *authenticatedStream) Context() context.Context {
 // This ensures that helpful suggestions (like "run azd auth login") are preserved
 // when errors are transmitted over gRPC, where only the error message string is sent.
 //
-// Auth-related errors (ReLoginRequiredError, ErrNoCurrentUser) are returned with
-// codes.Unauthenticated so that extensions can detect auth failures via gRPC status code.
+// Auth-related errors are returned with codes.Unauthenticated and a structured
+// ErrorInfo reason so extensions can reliably classify them as auth failures
+// while still distinguishing the remediation path.
 func wrapErrorWithSuggestion(err error) error {
 	if err == nil {
 		return nil
 	}
 
-	_, loginErr := errors.AsType[*auth.ReLoginRequiredError](err)
-	isAuthErr := errors.Is(err, auth.ErrNoCurrentUser) || loginErr
+	isAuthErr := isAuthError(err)
 
 	if suggestionErr, ok := errors.AsType[*internal.ErrorWithSuggestion](err); ok {
 		msg := fmt.Sprintf("%s\n%s", err.Error(), suggestionErr.Suggestion)
 		if isAuthErr {
-			return status.Error(codes.Unauthenticated, msg)
+			return grpcAuthStatus(err, msg)
 		}
 		return fmt.Errorf("%w\n%s", err, suggestionErr.Suggestion)
 	}
 
 	if isAuthErr {
-		return status.Error(codes.Unauthenticated, err.Error())
+		return grpcAuthStatus(err, err.Error())
 	}
 
 	return err
 }
 
+// isAuthError reports whether err's chain contains a known auth-failure type that should be
+// surfaced over gRPC as codes.Unauthenticated.
+func isAuthError(err error) bool {
+	if errors.Is(err, auth.ErrNoCurrentUser) {
+		return true
+	}
+	if _, ok := errors.AsType[*auth.ReLoginRequiredError](err); ok {
+		return true
+	}
+	if _, ok := errors.AsType[*auth.AuthFailedError](err); ok {
+		return true
+	}
+	return false
+}
+
+func grpcAuthStatus(err error, msg string) error {
+	st := status.New(codes.Unauthenticated, msg)
+	reason := grpcAuthReason(err)
+	if reason == "" {
+		return st.Err()
+	}
+
+	withDetails, detailErr := st.WithDetails(&errdetails.ErrorInfo{
+		Reason: reason,
+		Domain: azdext.AuthErrorDomain,
+	})
+	if detailErr != nil {
+		return st.Err()
+	}
+
+	return withDetails.Err()
+}
+
+func grpcAuthReason(err error) string {
+	if errors.Is(err, auth.ErrNoCurrentUser) {
+		return azdext.AuthErrorReasonNotLoggedIn
+	}
+
+	// Pass through the originating AAD error code (e.g., "AADSTS530084") when available.
+	// This preserves Entra's own semantics rather than redefining them on azd's side.
+	if authFailed, ok := errors.AsType[*auth.AuthFailedError](err); ok {
+		if authFailed.Parsed != nil && len(authFailed.Parsed.ErrorCodes) > 0 {
+			return fmt.Sprintf("AADSTS%d", authFailed.Parsed.ErrorCodes[0])
+		}
+	}
+
+	if _, ok := errors.AsType[*auth.ReLoginRequiredError](err); ok {
+		return azdext.AuthErrorReasonLoginRequired
+	}
+
+	return ""
+}
+
 func generateSigningKey() ([]byte, error) {
 	bytes := make([]byte, 32) // 256-bit HMAC signing key
 	if _, err := rand.Read(bytes); err != nil {

cli/azd/internal/grpcserver/server_coverage3_test.go

@@ -11,8 +11,10 @@ import (
 
 	"github.com/azure/azure-dev/cli/azd/internal"
 	"github.com/azure/azure-dev/cli/azd/pkg/auth"
+	"github.com/azure/azure-dev/cli/azd/pkg/azdext"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
+	"google.golang.org/genproto/googleapis/rpc/errdetails"
 	"google.golang.org/grpc"
 	"google.golang.org/grpc/codes"
 	"google.golang.org/grpc/metadata"
@@ -77,6 +79,33 @@ func TestWrapErrorWithSuggestion_ReLoginRequired(t *testing.T) {
 	require.Equal(t, codes.Unauthenticated, st.Code())
 }
 
+func TestWrapErrorWithSuggestion_TokenProtectionBlocked(t *testing.T) {
+	t.Parallel()
+	authFailed := &auth.AuthFailedError{
+		Parsed: &auth.AadErrorResponse{
+			Error:      "invalid_grant",
+			ErrorCodes: []int{530084},
+		},
+	}
+	// In production the wrapper is built by newActionableAuthError; mirror that shape here so
+	// wrapErrorWithSuggestion classifies the wrapped *AuthFailedError as an auth interaction.
+	err := fmt.Errorf("token protection: %w", &internal.ErrorWithSuggestion{
+		Err:        authFailed,
+		Suggestion: "Contact your IT administrator or request a policy exception.",
+	})
+
+	wrapped := wrapErrorWithSuggestion(err)
+	st, ok := status.FromError(wrapped)
+	require.True(t, ok)
+	require.Equal(t, codes.Unauthenticated, st.Code())
+	details := st.Details()
+	require.Len(t, details, 1)
+	info, ok := details[0].(*errdetails.ErrorInfo)
+	require.True(t, ok)
+	require.Equal(t, azdext.AuthErrorDomain, info.Domain)
+	require.Equal(t, "AADSTS530084", info.Reason)
+}
+
 func TestWrapErrorWithSuggestion_AuthErrorWithSuggestion(t *testing.T) {
 	t.Parallel()
 	inner := auth.ErrNoCurrentUser

cli/azd/internal/grpcserver/server_test.go

@@ -18,6 +18,7 @@ import (
 	"github.com/azure/azure-dev/cli/azd/pkg/azdext"
 	"github.com/azure/azure-dev/cli/azd/pkg/extensions"
 	"github.com/stretchr/testify/require"
+	"google.golang.org/genproto/googleapis/rpc/errdetails"
 	"google.golang.org/grpc/codes"
 	"google.golang.org/grpc/status"
 )
@@ -237,6 +238,7 @@ func Test_wrapErrorWithSuggestion(t *testing.T) {
 		wantContain      string
 		wantSameInstance bool
 		wantGrpcCode     codes.Code
+		wantAuthReason   string
 	}{
 		{
 			name:    "nil error returns nil",
@@ -266,25 +268,43 @@ func Test_wrapErrorWithSuggestion(t *testing.T) {
 			wantContain: "azd auth login",
 		},
 		{
-			name:         "ErrNoCurrentUser returns Unauthenticated",
-			err:          auth.ErrNoCurrentUser,
-			wantContain:  "not logged in",
-			wantGrpcCode: codes.Unauthenticated,
+			name:           "ErrNoCurrentUser returns Unauthenticated",
+			err:            auth.ErrNoCurrentUser,
+			wantContain:    "not logged in",
+			wantGrpcCode:   codes.Unauthenticated,
+			wantAuthReason: azdext.AuthErrorReasonNotLoggedIn,
 		},
 		{
-			name:         "wrapped ErrNoCurrentUser returns Unauthenticated",
-			err:          fmt.Errorf("failed to list subscriptions: %w", auth.ErrNoCurrentUser),
-			wantContain:  "not logged in",
-			wantGrpcCode: codes.Unauthenticated,
+			name:           "wrapped ErrNoCurrentUser returns Unauthenticated",
+			err:            fmt.Errorf("failed to list subscriptions: %w", auth.ErrNoCurrentUser),
+			wantContain:    "not logged in",
+			wantGrpcCode:   codes.Unauthenticated,
+			wantAuthReason: azdext.AuthErrorReasonNotLoggedIn,
 		},
 		{
 			name: "ReLoginRequiredError with suggestion returns Unauthenticated",
 			err: &internal.ErrorWithSuggestion{
 				Err:        &auth.ReLoginRequiredError{},
 				Suggestion: "login expired, run `azd auth login` to acquire a new token.",
 			},
-			wantContain:  "azd auth login",
-			wantGrpcCode: codes.Unauthenticated,
+			wantContain:    "azd auth login",
+			wantGrpcCode:   codes.Unauthenticated,
+			wantAuthReason: azdext.AuthErrorReasonLoginRequired,
+		},
+		{
+			name: "TokenProtectionBlockedError with suggestion returns Unauthenticated",
+			err: &internal.ErrorWithSuggestion{
+				Err: &auth.AuthFailedError{
+					Parsed: &auth.AadErrorResponse{
+						Error:      "invalid_grant",
+						ErrorCodes: []int{530084},
+					},
+				},
+				Suggestion: "Contact your IT administrator or request a policy exception.",
+			},
+			wantContain:    "policy exception",
+			wantGrpcCode:   codes.Unauthenticated,
+			wantAuthReason: "AADSTS530084",
 		},
 	}
 
@@ -304,6 +324,14 @@ func Test_wrapErrorWithSuggestion(t *testing.T) {
 				st, ok := status.FromError(result)
 				require.True(t, ok, "expected gRPC status error")
 				require.Equal(t, tt.wantGrpcCode, st.Code())
+				if tt.wantAuthReason != "" {
+					details := st.Details()
+					require.Len(t, details, 1)
+					info, ok := details[0].(*errdetails.ErrorInfo)
+					require.True(t, ok, "expected ErrorInfo detail")
+					require.Equal(t, azdext.AuthErrorDomain, info.Domain)
+					require.Equal(t, tt.wantAuthReason, info.Reason)
+				}
 			}
 		})
 	}

cli/azd/pkg/auth/azd_credential.go

@@ -75,7 +75,7 @@ func (c *azdCredential) GetToken(ctx context.Context, options policy.TokenReques
 		c.cacheTracer.LogSnapshotOnce(failurePhase)
 
 		if authFailed, ok := errors.AsType[*AuthFailedError](err); ok {
-			if loginErr, ok := newReLoginRequiredError(authFailed.Parsed, options.Scopes, c.cloud, tenantID); ok {
+			if loginErr, ok := newActionableAuthError(authFailed.Parsed, options.Scopes, c.cloud, tenantID, authFailed); ok {
 				log.Println(authFailed.httpErrorDetails())
 
 				if options.Claims != "" {