Fix health-check close failing auth in vMCP BackendClient

pkg/vmcp/auth/strategies/header_injection_test.go

@@ -13,7 +13,7 @@ import (
 	"github.com/stretchr/testify/require"
 
 	authtypes "github.com/stacklok/toolhive/pkg/vmcp/auth/types"
-	"github.com/stacklok/toolhive/pkg/vmcp/health"
+	healthcontext "github.com/stacklok/toolhive/pkg/vmcp/health/context"
 )
 
 func TestHeaderInjectionStrategy_Name(t *testing.T) {
@@ -43,7 +43,7 @@ func TestHeaderInjectionStrategy_Authenticate(t *testing.T) {
 					HeaderValue: "secret-key-123",
 				},
 			},
-			setupCtx:    func() context.Context { return health.WithHealthCheckMarker(context.Background()) },
+			setupCtx:    func() context.Context { return healthcontext.WithHealthCheckMarker(context.Background()) },
 			expectError: false,
 			checkHeader: func(t *testing.T, req *http.Request) {
 				t.Helper()

pkg/vmcp/auth/strategies/tokenexchange.go

@@ -18,7 +18,7 @@ import (
 	"github.com/stacklok/toolhive/pkg/auth"
 	"github.com/stacklok/toolhive/pkg/auth/tokenexchange"
 	authtypes "github.com/stacklok/toolhive/pkg/vmcp/auth/types"
-	"github.com/stacklok/toolhive/pkg/vmcp/health"
+	healthcontext "github.com/stacklok/toolhive/pkg/vmcp/health/context"
 )
 
 const (
@@ -107,7 +107,7 @@ func (s *TokenExchangeStrategy) Authenticate(
 	// For health checks there is no user identity to exchange. If client credentials
 	// are configured, use a client credentials grant to authenticate the probe request.
 	// Otherwise skip authentication — the backend will be probed unauthenticated.
-	if health.IsHealthCheck(ctx) {
+	if healthcontext.IsHealthCheck(ctx) {
 		if config.ClientID != "" && config.ClientSecret != "" {
 			return s.authenticateWithClientCredentials(ctx, req, config)
 		}

pkg/vmcp/auth/strategies/tokenexchange_test.go

@@ -18,7 +18,7 @@ import (
 	"github.com/stacklok/toolhive-core/env/mocks"
 	"github.com/stacklok/toolhive/pkg/auth"
 	authtypes "github.com/stacklok/toolhive/pkg/vmcp/auth/types"
-	"github.com/stacklok/toolhive/pkg/vmcp/health"
+	healthcontext "github.com/stacklok/toolhive/pkg/vmcp/health/context"
 )
 
 // Test constants
@@ -108,7 +108,7 @@ func TestTokenExchangeStrategy_Authenticate(t *testing.T) {
 	}{
 		{
 			name:     "health check without client credentials skips authentication",
-			setupCtx: func() context.Context { return health.WithHealthCheckMarker(context.Background()) },
+			setupCtx: func() context.Context { return healthcontext.WithHealthCheckMarker(context.Background()) },
 			setupServer: func() *httptest.Server {
 				return httptest.NewServer(http.HandlerFunc(func(_ http.ResponseWriter, _ *http.Request) {
 					t.Error("token endpoint should not be called when no client credentials are configured")
@@ -125,7 +125,7 @@ func TestTokenExchangeStrategy_Authenticate(t *testing.T) {
 		},
 		{
 			name:     "health check with client credentials uses client credentials grant",
-			setupCtx: func() context.Context { return health.WithHealthCheckMarker(context.Background()) },
+			setupCtx: func() context.Context { return healthcontext.WithHealthCheckMarker(context.Background()) },
 			setupServer: func() *httptest.Server {
 				return httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 					t.Helper()

pkg/vmcp/auth/strategies/upstream_inject.go

@@ -10,7 +10,7 @@ import (
 
 	"github.com/stacklok/toolhive/pkg/auth"
 	authtypes "github.com/stacklok/toolhive/pkg/vmcp/auth/types"
-	"github.com/stacklok/toolhive/pkg/vmcp/health"
+	healthcontext "github.com/stacklok/toolhive/pkg/vmcp/health/context"
 )
 
 // UpstreamInjectStrategy injects an upstream IDP token into backend request headers.
@@ -62,7 +62,7 @@ func (*UpstreamInjectStrategy) Authenticate(
 	ctx context.Context, req *http.Request, strategy *authtypes.BackendAuthStrategy,
 ) error {
 	// Health checks have no user identity — skip authentication.
-	if health.IsHealthCheck(ctx) {
+	if healthcontext.IsHealthCheck(ctx) {
 		return nil
 	}
 

pkg/vmcp/auth/strategies/upstream_inject_test.go

@@ -14,7 +14,7 @@ import (
 	"github.com/stretchr/testify/require"
 
 	authtypes "github.com/stacklok/toolhive/pkg/vmcp/auth/types" // BackendAuthStrategy, ErrUpstreamTokenNotFound
-	"github.com/stacklok/toolhive/pkg/vmcp/health"
+	healthcontext "github.com/stacklok/toolhive/pkg/vmcp/health/context"
 )
 
 func TestUpstreamInjectStrategy_Name(t *testing.T) {
@@ -118,7 +118,7 @@ func TestUpstreamInjectStrategy_Authenticate(t *testing.T) {
 		},
 		{
 			name:     "health check bypass",
-			setupCtx: func() context.Context { return health.WithHealthCheckMarker(context.Background()) },
+			setupCtx: func() context.Context { return healthcontext.WithHealthCheckMarker(context.Background()) },
 			strategy: &authtypes.BackendAuthStrategy{
 				Type: authtypes.StrategyTypeUpstreamInject,
 				UpstreamInject: &authtypes.UpstreamInjectConfig{

pkg/vmcp/client/client.go

@@ -29,6 +29,7 @@ import (
 	vmcpauth "github.com/stacklok/toolhive/pkg/vmcp/auth"
 	authtypes "github.com/stacklok/toolhive/pkg/vmcp/auth/types"
 	"github.com/stacklok/toolhive/pkg/vmcp/conversion"
+	healthcontext "github.com/stacklok/toolhive/pkg/vmcp/health/context"
 )
 
 const (
@@ -116,19 +117,31 @@ func (f roundTripperFunc) RoundTrip(req *http.Request) (*http.Response, error) {
 	return f(req)
 }
 
-// identityPropagatingRoundTripper propagates identity to backend HTTP requests.
+// identityPropagatingRoundTripper propagates identity and health-check markers to backend HTTP requests.
 // This ensures that identity information from the vMCP handler is available for authentication
 // strategies that need it (e.g., token exchange).
+//
+// The health-check marker is stored at transport creation time and re-injected into every
+// outgoing request, including the DELETE that mcp-go sends when closing a streamable-HTTP
+// session. Without this, mcp-go's Close() creates a fresh context.Background()-based request
+// that loses the health-check marker, causing auth strategies (UpstreamInjectStrategy,
+// TokenExchangeStrategy) to fail with "no identity found in context".
 type identityPropagatingRoundTripper struct {
-	base     http.RoundTripper
-	identity *auth.Identity
+	base          http.RoundTripper
+	identity      *auth.Identity
+	isHealthCheck bool
 }
 
-// RoundTrip implements http.RoundTripper by adding identity to the request context.
+// RoundTrip implements http.RoundTripper by adding identity and health-check marker to the request context.
 func (i *identityPropagatingRoundTripper) RoundTrip(req *http.Request) (*http.Response, error) {
+	ctx := req.Context()
 	if i.identity != nil {
-		// Add identity to the request's context
-		ctx := auth.WithIdentity(req.Context(), i.identity)
+		ctx = auth.WithIdentity(ctx, i.identity)
+	}
+	if i.isHealthCheck {
+		ctx = healthcontext.WithHealthCheckMarker(ctx)
+	}
+	if i.identity != nil || i.isHealthCheck {
 		req = req.Clone(ctx)
 	}
 	return i.base.RoundTrip(req)
@@ -227,12 +240,16 @@ func (h *httpBackendClient) defaultClientFactory(ctx context.Context, target *vm
 		target:       target,
 	}
 
-	// Extract identity from context and propagate it to backend requests
-	// This ensures authentication strategies (e.g., token exchange) can access identity
+	// Extract identity and health-check marker from context and propagate them to backend
+	// requests. The health-check marker must be carried through to the DELETE request that
+	// mcp-go emits when closing a streamable-HTTP session: mcp-go creates that request with
+	// context.Background(), which loses both the identity and the health-check marker that
+	// were present on the original ListCapabilities call context.
 	identity, _ := auth.IdentityFromContext(ctx)
 	baseTransport = &identityPropagatingRoundTripper{
-		base:     baseTransport,
-		identity: identity,
+		base:          baseTransport,
+		identity:      identity,
+		isHealthCheck: healthcontext.IsHealthCheck(ctx),
 	}
 
 	// Inject W3C Trace Context headers (traceparent/tracestate) into outgoing requests.

pkg/vmcp/client/client_test.go

@@ -22,11 +22,13 @@ import (
 	"go.opentelemetry.io/otel/trace"
 	"go.uber.org/mock/gomock"
 
+	pkgauth "github.com/stacklok/toolhive/pkg/auth"
 	"github.com/stacklok/toolhive/pkg/vmcp"
 	"github.com/stacklok/toolhive/pkg/vmcp/auth"
 	authmocks "github.com/stacklok/toolhive/pkg/vmcp/auth/mocks"
 	"github.com/stacklok/toolhive/pkg/vmcp/auth/strategies"
 	authtypes "github.com/stacklok/toolhive/pkg/vmcp/auth/types"
+	healthcontext "github.com/stacklok/toolhive/pkg/vmcp/health/context"
 )
 
 func TestHTTPBackendClient_ListCapabilities_WithMockFactory(t *testing.T) {
@@ -855,3 +857,125 @@ func TestWrapBackendError(t *testing.T) {
 		})
 	}
 }
+
+// ---------------------------------------------------------------------------
+// identityPropagatingRoundTripper
+// ---------------------------------------------------------------------------
+
+func TestIdentityPropagatingRoundTripper_WithIdentity_PropagatesIdentityInContext(t *testing.T) {
+	t.Parallel()
+
+	base := &mockRoundTripper{response: &http.Response{StatusCode: http.StatusOK}}
+	identity := &pkgauth.Identity{PrincipalInfo: pkgauth.PrincipalInfo{Subject: "user-1"}}
+	rt := &identityPropagatingRoundTripper{base: base, identity: identity}
+
+	req, err := http.NewRequestWithContext(context.Background(), http.MethodGet, "http://backend.example.com/mcp", nil)
+	require.NoError(t, err)
+
+	_, err = rt.RoundTrip(req)
+	require.NoError(t, err)
+
+	require.NotNil(t, base.capturedReq)
+	got, ok := pkgauth.IdentityFromContext(base.capturedReq.Context())
+	require.True(t, ok, "identity should be in downstream request context")
+	assert.Equal(t, "user-1", got.Subject)
+}
+
+func TestIdentityPropagatingRoundTripper_NilIdentity_NoIdentityInContext(t *testing.T) {
+	t.Parallel()
+
+	base := &mockRoundTripper{response: &http.Response{StatusCode: http.StatusOK}}
+	rt := &identityPropagatingRoundTripper{base: base, identity: nil}
+
+	req, err := http.NewRequestWithContext(context.Background(), http.MethodGet, "http://backend.example.com/mcp", nil)
+	require.NoError(t, err)
+
+	_, err = rt.RoundTrip(req)
+	require.NoError(t, err)
+
+	require.NotNil(t, base.capturedReq)
+	_, ok := pkgauth.IdentityFromContext(base.capturedReq.Context())
+	assert.False(t, ok, "no identity should be in downstream context when nil identity configured")
+}
+
+func TestIdentityPropagatingRoundTripper_HealthCheck_PropagatesMarker(t *testing.T) {
+	t.Parallel()
+
+	base := &mockRoundTripper{response: &http.Response{StatusCode: http.StatusOK}}
+	rt := &identityPropagatingRoundTripper{base: base, identity: nil, isHealthCheck: true}
+
+	// Simulate mcp-go Close(): request created with context.Background(), no health check marker.
+	req, err := http.NewRequestWithContext(context.Background(), http.MethodDelete, "http://backend.example.com/mcp", nil)
+	require.NoError(t, err)
+
+	_, err = rt.RoundTrip(req)
+	require.NoError(t, err)
+
+	require.NotNil(t, base.capturedReq)
+	assert.True(t, healthcontext.IsHealthCheck(base.capturedReq.Context()),
+		"health check marker should be propagated even when original request context lacks it")
+}
+
+func TestIdentityPropagatingRoundTripper_NonHealthCheck_NoMarkerAdded(t *testing.T) {
+	t.Parallel()
+
+	base := &mockRoundTripper{response: &http.Response{StatusCode: http.StatusOK}}
+	rt := &identityPropagatingRoundTripper{base: base, identity: nil, isHealthCheck: false}
+
+	req, err := http.NewRequestWithContext(context.Background(), http.MethodGet, "http://backend.example.com/mcp", nil)
+	require.NoError(t, err)
+
+	_, err = rt.RoundTrip(req)
+	require.NoError(t, err)
+
+	require.NotNil(t, base.capturedReq)
+	assert.False(t, healthcontext.IsHealthCheck(base.capturedReq.Context()),
+		"health check marker should not be injected for non-health-check transports")
+}
+
+func TestIdentityPropagatingRoundTripper_HealthCheckWithIdentity_PropagatesBoth(t *testing.T) {
+	t.Parallel()
+
+	base := &mockRoundTripper{response: &http.Response{StatusCode: http.StatusOK}}
+	identity := &pkgauth.Identity{PrincipalInfo: pkgauth.PrincipalInfo{Subject: "svc-account"}}
+	rt := &identityPropagatingRoundTripper{base: base, identity: identity, isHealthCheck: true}
+
+	req, err := http.NewRequestWithContext(context.Background(), http.MethodGet, "http://backend.example.com/mcp", nil)
+	require.NoError(t, err)
+
+	_, err = rt.RoundTrip(req)
+	require.NoError(t, err)
+
+	require.NotNil(t, base.capturedReq)
+	got, ok := pkgauth.IdentityFromContext(base.capturedReq.Context())
+	require.True(t, ok)
+	assert.Equal(t, "svc-account", got.Subject)
+	assert.True(t, healthcontext.IsHealthCheck(base.capturedReq.Context()))
+}
+
+// TestIdentityPropagatingRoundTripper_HealthCheckClose_OriginalRequestContextUnchanged verifies
+// that when the transport is in health-check mode, RoundTrip injects the health-check marker
+// into the downstream request's context without mutating the original request context. This
+// covers requests (e.g. the DELETE mcp-go emits on Close()) whose context does not already
+// carry the marker.
+func TestIdentityPropagatingRoundTripper_HealthCheckClose_OriginalRequestContextUnchanged(t *testing.T) {
+	t.Parallel()
+
+	base := &mockRoundTripper{response: &http.Response{StatusCode: http.StatusOK}}
+	rt := &identityPropagatingRoundTripper{base: base, identity: nil, isHealthCheck: true}
+
+	originalCtx := context.Background() // no health check marker — simulates mcp-go Close()
+	req, err := http.NewRequestWithContext(originalCtx, http.MethodDelete, "http://backend.example.com/mcp", nil)
+	require.NoError(t, err)
+
+	_, err = rt.RoundTrip(req)
+	require.NoError(t, err)
+
+	// Original request context must NOT be modified.
+	assert.False(t, healthcontext.IsHealthCheck(originalCtx),
+		"original request context must not be mutated")
+	// But downstream context MUST have the marker.
+	require.NotNil(t, base.capturedReq)
+	assert.True(t, healthcontext.IsHealthCheck(base.capturedReq.Context()),
+		"downstream request must carry health check marker")
+}

pkg/vmcp/health/context/context.go

@@ -0,0 +1,33 @@
+// SPDX-FileCopyrightText: Copyright 2025 Stacklok, Inc.
+// SPDX-License-Identifier: Apache-2.0
+
+// Package healthcontext provides a lightweight, dependency-free context marker
+// for identifying health check requests. Keeping this in a separate package
+// allows packages like pkg/vmcp/client and pkg/vmcp/auth/strategies to use
+// the marker without pulling in the heavyweight pkg/vmcp/health dependencies
+// (e.g. k8s.io/apimachinery).
+package healthcontext
+
+import "context"
+
+// healthCheckContextKey is an unexported key type for the health check marker.
+type healthCheckContextKey struct{}
+
+// WithHealthCheckMarker marks a context as a health check request.
+// Authentication layers can use IsHealthCheck to identify and skip authentication
+// for health check requests.
+func WithHealthCheckMarker(ctx context.Context) context.Context {
+	return context.WithValue(ctx, healthCheckContextKey{}, true)
+}
+
+// IsHealthCheck returns true if the context is marked as a health check.
+// Authentication strategies use this to bypass authentication for health checks,
+// since health checks verify backend availability and should not require user credentials.
+// Returns false for nil contexts.
+func IsHealthCheck(ctx context.Context) bool {
+	if ctx == nil {
+		return false
+	}
+	val, ok := ctx.Value(healthCheckContextKey{}).(bool)
+	return ok && val
+}

pkg/vmcp/health/context/context_test.go

@@ -0,0 +1,25 @@
+// SPDX-FileCopyrightText: Copyright 2025 Stacklok, Inc.
+// SPDX-License-Identifier: Apache-2.0
+
+package healthcontext
+
+import (
+	"context"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestIsHealthCheck_WrongValueType(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.WithValue(context.Background(), healthCheckContextKey{}, "not-a-bool")
+	assert.False(t, IsHealthCheck(ctx), "non-bool value should not be treated as health check marker")
+}
+
+func TestIsHealthCheck_FalseValue(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.WithValue(context.Background(), healthCheckContextKey{}, false)
+	assert.False(t, IsHealthCheck(ctx), "explicit false value should not be treated as health check marker")
+}

pkg/vmcp/health/monitor.go

@@ -14,28 +14,22 @@ import (
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 
 	"github.com/stacklok/toolhive/pkg/vmcp"
+	healthcontext "github.com/stacklok/toolhive/pkg/vmcp/health/context"
 )
 
-// healthCheckContextKey is a marker for health check requests.
-type healthCheckContextKey struct{}
-
 // WithHealthCheckMarker marks a context as a health check request.
 // Authentication layers can use IsHealthCheck to identify and skip authentication
 // for health check requests.
 func WithHealthCheckMarker(ctx context.Context) context.Context {
-	return context.WithValue(ctx, healthCheckContextKey{}, true)
+	return healthcontext.WithHealthCheckMarker(ctx)
 }
 
 // IsHealthCheck returns true if the context is marked as a health check.
 // Authentication strategies use this to bypass authentication for health checks,
 // since health checks verify backend availability and should not require user credentials.
 // Returns false for nil contexts.
 func IsHealthCheck(ctx context.Context) bool {
-	if ctx == nil {
-		return false
-	}
-	val, ok := ctx.Value(healthCheckContextKey{}).(bool)
-	return ok && val
+	return healthcontext.IsHealthCheck(ctx)
 }
 
 // StatusProvider provides read-only access to backend health status.