diff --git a/coderd/coderd.go b/coderd/coderd.go
index ab046242d9..07746322e6 100644
--- a/coderd/coderd.go
+++ b/coderd/coderd.go
@@ -74,6 +74,7 @@ import (
 	"github.com/coder/coder/v2/coderd/httpmw"
 	"github.com/coder/coder/v2/coderd/httpmw/loggermw"
 	"github.com/coder/coder/v2/coderd/idpsync"
+	"github.com/coder/coder/v2/coderd/mcp"
 	"github.com/coder/coder/v2/coderd/metricscache"
 	"github.com/coder/coder/v2/coderd/notifications"
 	"github.com/coder/coder/v2/coderd/oauth2provider"
@@ -1106,7 +1107,7 @@ func New(options *Options) *API {
 	// and in the build info response and the AI bridge config, so a runtime
 	// toggle would have to update all three.
 	oauth2ProviderEnabled := api.DeploymentValues.OAuth2.Provider.Enable.Value()
-	apiKeyMiddleware := httpmw.ExtractAPIKeyMW(httpmw.ExtractAPIKeyConfig{
+	apiKeyConfig := httpmw.ExtractAPIKeyConfig{
 		DB:                            options.Database,
 		ActivateDormantUser:           ActivateDormantUser(options.Logger, &api.Auditor, options.Database),
 		OAuth2Configs:                 oauthConfigs,
@@ -1117,7 +1118,8 @@ func New(options *Options) *API {
 		PostAuthAdditionalHeadersFunc: options.PostAuthAdditionalHeadersFunc,
 		Logger:                        options.Logger,
 		AccessURL:                     options.AccessURL,
-	})
+	}
+	apiKeyMiddleware := httpmw.ExtractAPIKeyMW(apiKeyConfig)
 	// Same as above but it redirects to the login page.
 	apiKeyMiddlewareRedirect := httpmw.ExtractAPIKeyMW(httpmw.ExtractAPIKeyConfig{
 		DB:                            options.Database,
@@ -1405,13 +1407,32 @@ func New(options *Options) *API {
 		})
 
 		r.Route("/mcp", func(r chi.Router) {
-			r.Use(apiKeyMiddleware)
 			// Providers pin the redirect URI when a session is established,
 			// so the callback URL cannot change for existing sessions without
 			// breaking token refresh and forcing a re-auth.
-			r.Get("/servers/{mcpServer}/oauth2/callback", api.mcpServerOAuth2Callback)
+			r.With(apiKeyMiddleware).Get("/servers/{mcpServer}/oauth2/callback", api.mcpServerOAuth2Callback)
 			// MCP HTTP transport endpoint with mandatory authentication.
 			r.Route("/http", func(r chi.Router) {
+				r.Use(func(next http.Handler) http.Handler {
+					cfg := apiKeyConfig
+					cfg.ResourceURI = options.AccessURL.JoinPath(mcp.MCPEndpoint).String()
+					cfg.ResourceMetadataURL = options.AccessURL.JoinPath("/.well-known/oauth-protected-resource", mcp.MCPEndpoint).String()
+					canonical := httpmw.ExtractAPIKeyMW(cfg)(next)
+					cfg.ResourceMetadataURL = options.AccessURL.JoinPath("/.well-known/oauth-protected-resource", mcp.MCPEndpoint+"/").String()
+					trailingSlash := httpmw.ExtractAPIKeyMW(cfg)(next)
+					return http.HandlerFunc(func(rw http.ResponseWriter, r *http.Request) {
+						// Routing normalizes slashes, but OAuth resource identity
+						// must not admit aliases or arbitrary descendant paths.
+						switch r.URL.EscapedPath() {
+						case mcp.MCPEndpoint:
+							canonical.ServeHTTP(rw, r)
+						case mcp.MCPEndpoint + "/":
+							trailingSlash.ServeHTTP(rw, r)
+						default:
+							httpapi.RouteNotFound(rw)
+						}
+					})
+				})
 				r.Use(
 					httpmw.RequireOAuth2Provider(oauth2ProviderEnabled),
 					httpmw.RequireExperiment(api.Experiments, codersdk.ExperimentMCPServerHTTP),
diff --git a/coderd/httpmw/apikey.go b/coderd/httpmw/apikey.go
index 66cb038ce6..5bd731ca04 100644
--- a/coderd/httpmw/apikey.go
+++ b/coderd/httpmw/apikey.go
@@ -34,8 +34,25 @@ import (
 type (
 	apiKeyContextKey           struct{}
 	apiKeyPrecheckedContextKey struct{}
+	apiKeyDelegationContextKey struct{}
 )
 
+type apiKeyDelegation struct {
+	resourceURI string
+	apiKeyID    string
+}
+
+// WithAPIKeyDelegation binds server-owned, in-process work to the originating
+// resource URI and authenticated API key. Never derive these values from HTTP
+// headers or query parameters. The original credential must still pass
+// validation, including its audience, scopes, and expiry.
+func WithAPIKeyDelegation(ctx context.Context, resourceURI, apiKeyID string) context.Context {
+	return context.WithValue(ctx, apiKeyDelegationContextKey{}, apiKeyDelegation{
+		resourceURI: resourceURI,
+		apiKeyID:    apiKeyID,
+	})
+}
+
 // ValidateAPIKeyConfig holds the settings needed for API key
 // validation at the top of the request lifecycle. Unlike
 // ExtractAPIKeyConfig it omits route-specific fields
@@ -175,9 +192,17 @@ type ExtractAPIKeyConfig struct {
 	PostAuthAdditionalHeadersFunc func(a rbac.Subject, header http.Header)
 
 	// AccessURL is the configured access URL for this Coder deployment.
-	// Used for generating OAuth2 resource metadata URLs in WWW-Authenticate headers.
+	// It supplies the default OAuth2 resource URI and metadata URL.
 	AccessURL *url.URL
 
+	// ResourceURI overrides the OAuth2 audience expected by this route.
+	// Empty uses the deployment access URL, or the request origin if unset.
+	ResourceURI string
+
+	// ResourceMetadataURL overrides the OAuth2 discovery URL advertised in
+	// WWW-Authenticate. Empty uses the deployment's root metadata endpoint.
+	ResourceMetadataURL string
+
 	// Logger is used for logging middleware operations.
 	Logger slog.Logger
 }
@@ -265,6 +290,13 @@ func ValidateAPIKey(ctx context.Context, cfg ValidateAPIKeyConfig, r *http.Reque
 		return nil, valErr
 	}
 
+	if delegation, ok := ctx.Value(apiKeyDelegationContextKey{}).(apiKeyDelegation); ok && delegation.apiKeyID != key.ID {
+		return nil, &ValidateAPIKeyError{
+			Code:     http.StatusUnauthorized,
+			Response: codersdk.Response{Message: "Delegated requests must use the credential that authenticated the originating request."},
+		}
+	}
+
 	// Log the API key ID for all requests that have a valid key
 	// format and secret, regardless of whether subsequent validation
 	// (expiry, user status, etc.) succeeds.
@@ -628,7 +660,7 @@ func ExtractAPIKey(rw http.ResponseWriter, r *http.Request, cfg ExtractAPIKeyCon
 
 		// Add WWW-Authenticate header for 401/403 responses (RFC 6750 + RFC 9728)
 		if code == http.StatusUnauthorized || code == http.StatusForbidden {
-			rw.Header().Set("WWW-Authenticate", buildWWWAuthenticateHeader(cfg.AccessURL, r, code, response))
+			rw.Header().Set("WWW-Authenticate", buildWWWAuthenticateHeader(cfg.AccessURL, cfg.ResourceMetadataURL, r, code, response))
 		}
 
 		httpapi.Write(ctx, rw, code, response)
@@ -701,7 +733,11 @@ func ExtractAPIKey(rw http.ResponseWriter, r *http.Request, cfg ExtractAPIKeyCon
 
 	// Validate OAuth2 provider app token audience (RFC 8707) if applicable.
 	if key.LoginType == database.LoginTypeOAuth2ProviderApp {
-		if err := validateOAuth2ProviderAppTokenAudience(ctx, cfg.DB, *key, cfg.AccessURL, r); err != nil {
+		resourceURI := cfg.ResourceURI
+		if resourceURI == "" {
+			resourceURI = extractExpectedAudience(cfg.AccessURL, r)
+		}
+		if err := validateOAuth2ProviderAppTokenAudience(ctx, cfg.DB, *key, resourceURI); err != nil {
 			// Log the detailed error for debugging but don't expose it to the client.
 			cfg.Logger.Debug(ctx, "oauth2 token audience validation failed", slog.Error(err))
 			return optionalWrite(http.StatusForbidden, codersdk.Response{
@@ -742,7 +778,7 @@ func ExtractAPIKey(rw http.ResponseWriter, r *http.Request, cfg ExtractAPIKeyCon
 
 // validateOAuth2ProviderAppTokenAudience validates that an OAuth2 provider app token
 // is being used with the correct audience/resource server (RFC 8707).
-func validateOAuth2ProviderAppTokenAudience(ctx context.Context, db database.Store, key database.APIKey, accessURL *url.URL, r *http.Request) error {
+func validateOAuth2ProviderAppTokenAudience(ctx context.Context, db database.Store, key database.APIKey, expectedAudience string) error {
 	// Get the OAuth2 provider app token to check its audience
 	//nolint:gocritic // OAuth2 system context — audience validation for provider app tokens
 	token, err := db.GetOAuth2ProviderAppTokenByAPIKeyID(dbauthz.AsSystemOAuth2(ctx), key.ID)
@@ -755,8 +791,11 @@ func validateOAuth2ProviderAppTokenAudience(ctx context.Context, db database.Sto
 		return nil
 	}
 
-	// Extract the expected audience from the access URL
-	expectedAudience := extractExpectedAudience(accessURL, r)
+	if delegation, ok := ctx.Value(apiKeyDelegationContextKey{}).(apiKeyDelegation); ok && delegation.apiKeyID == key.ID {
+		// Server-owned delegation validates the originating resource rather
+		// than the resource implementing the internal request.
+		expectedAudience = delegation.resourceURI
+	}
 
 	// Normalize both audience values for RFC 3986 compliant comparison
 	normalizedTokenAudience := normalizeAudienceURI(token.Audience.String)
@@ -878,7 +917,7 @@ func normalizePathSegments(path string) string {
 // Test export functions for testing package access
 
 // buildWWWAuthenticateHeader constructs RFC 6750 + RFC 9728 compliant WWW-Authenticate header
-func buildWWWAuthenticateHeader(accessURL *url.URL, r *http.Request, code int, response codersdk.Response) string {
+func buildWWWAuthenticateHeader(accessURL *url.URL, resourceMetadata string, r *http.Request, code int, response codersdk.Response) string {
 	// Use the configured access URL for resource metadata
 	if accessURL == nil {
 		scheme := "https"
@@ -893,7 +932,9 @@ func buildWWWAuthenticateHeader(accessURL *url.URL, r *http.Request, code int, r
 		}
 	}
 
-	resourceMetadata := accessURL.JoinPath("/.well-known/oauth-protected-resource").String()
+	if resourceMetadata == "" {
+		resourceMetadata = accessURL.JoinPath("/.well-known/oauth-protected-resource").String()
+	}
 
 	switch code {
 	case http.StatusUnauthorized:
@@ -920,8 +961,6 @@ func buildWWWAuthenticateHeader(accessURL *url.URL, r *http.Request, code int, r
 // extractExpectedAudience determines the expected audience for the current request.
 // This should match the resource parameter used during authorization.
 func extractExpectedAudience(accessURL *url.URL, r *http.Request) string {
-	// For MCP compliance, the audience should be the canonical URI of the resource server
-	// This typically matches the access URL of the Coder deployment
 	var audience string
 
 	if accessURL != nil {
diff --git a/coderd/httpmw/apikey_test.go b/coderd/httpmw/apikey_test.go
index a56b8a825f..5929cb57e3 100644
--- a/coderd/httpmw/apikey_test.go
+++ b/coderd/httpmw/apikey_test.go
@@ -3,11 +3,13 @@ package httpmw_test
 import (
 	"context"
 	"crypto/sha256"
+	"database/sql"
 	"encoding/json"
 	"fmt"
 	"io"
 	"net/http"
 	"net/http/httptest"
+	"net/url"
 	"strings"
 	"sync/atomic"
 	"testing"
@@ -39,6 +41,131 @@ import (
 	"github.com/coder/coder/v2/testutil"
 )
 
+func TestAPIKeyResource(t *testing.T) {
+	t.Parallel()
+
+	db, _ := dbtestutil.NewDB(t)
+	user := dbgen.User(t, db, database.User{})
+	app := dbgen.OAuth2ProviderApp(t, db, database.OAuth2ProviderApp{})
+	origin, err := url.Parse("https://coder.example.com")
+	require.NoError(t, err)
+	const (
+		reports  = "https://coder.example.com/reports"
+		jobs     = "https://coder.example.com/jobs"
+		metadata = "https://discovery.example.com/reports"
+	)
+
+	for _, tc := range []struct {
+		name              string
+		audience          string
+		resourceURI       string
+		delegatedResource string
+		wrongKey          bool
+		invalidSecret     bool
+		missingToken      bool
+		queryToken        bool
+		status            int
+	}{
+		{name: "DefaultRoot", audience: origin.String(), status: http.StatusNoContent},
+		{name: "DefaultRejectsPathAudience", audience: reports, status: http.StatusForbidden},
+		{name: "ReportsResource", audience: reports, resourceURI: reports, status: http.StatusNoContent},
+		{name: "JobsResource", audience: jobs, resourceURI: jobs, status: http.StatusNoContent},
+		{name: "NormalizedResource", audience: "https://CODER.example.com:443/reports/", resourceURI: reports, status: http.StatusNoContent},
+		{name: "ResourceRejectsRoot", audience: origin.String(), resourceURI: reports, status: http.StatusForbidden},
+		{name: "ResourceRejectsOtherResource", audience: jobs, resourceURI: reports, status: http.StatusForbidden},
+		{name: "ResourceRejectsOtherDeployment", audience: "https://other.example.com/reports", resourceURI: reports, status: http.StatusForbidden},
+		{name: "ReportsDelegation", audience: reports, delegatedResource: reports, status: http.StatusNoContent},
+		{name: "JobsDelegation", audience: jobs, delegatedResource: jobs, status: http.StatusNoContent},
+		{name: "DelegationOverridesDestinationResource", audience: reports, resourceURI: jobs, delegatedResource: reports, status: http.StatusNoContent},
+		{name: "DelegationRejectsDestinationAudience", audience: jobs, resourceURI: jobs, delegatedResource: reports, status: http.StatusForbidden},
+		{name: "DelegationRejectsRoot", audience: origin.String(), delegatedResource: reports, status: http.StatusForbidden},
+		{name: "DelegationRejectsOtherResource", audience: jobs, delegatedResource: reports, status: http.StatusForbidden},
+		{name: "DelegationRejectsOtherDeployment", audience: "https://other.example.com/reports", delegatedResource: reports, status: http.StatusForbidden},
+		{name: "DelegationRejectsSubstitutedKey", audience: reports, delegatedResource: reports, wrongKey: true, status: http.StatusUnauthorized},
+		{name: "DelegationRejectsInvalidSecret", audience: reports, delegatedResource: reports, invalidSecret: true, status: http.StatusUnauthorized},
+		{name: "DelegationRequiresCredential", audience: reports, delegatedResource: reports, missingToken: true, status: http.StatusUnauthorized},
+		{name: "DelegationRejectsQueryToken", audience: reports, delegatedResource: reports, queryToken: true, status: http.StatusUnauthorized},
+		{name: "ResourceDiscoveryWithoutCredential", resourceURI: reports, missingToken: true, status: http.StatusUnauthorized},
+		{name: "UnboundLegacyResource", resourceURI: reports, status: http.StatusNoContent},
+		{name: "UnboundLegacyDelegation", delegatedResource: reports, status: http.StatusNoContent},
+		{name: "UnboundLegacyRejectsSubstitutedKey", delegatedResource: reports, wrongKey: true, status: http.StatusUnauthorized},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+			key, token := dbgen.APIKey(t, db, database.APIKey{
+				UserID: user.ID, LoginType: database.LoginTypeOAuth2ProviderApp,
+				Scopes: database.APIKeyScopes{database.ApiKeyScopeUserRead},
+			})
+			dbgen.OAuth2ProviderAppToken(t, db, database.OAuth2ProviderAppToken{
+				AppID: app.ID, UserID: user.ID, APIKeyID: key.ID, HashPrefix: []byte(key.ID),
+				Audience: sql.NullString{String: tc.audience, Valid: tc.audience != ""},
+			})
+			delegatedID := key.ID
+			if tc.wrongKey {
+				otherKey, _ := dbgen.APIKey(t, db, database.APIKey{UserID: user.ID})
+				delegatedID = otherKey.ID
+			}
+			if tc.invalidSecret {
+				token = key.ID + "-" + strings.Repeat("0", 22)
+			}
+
+			for _, precheck := range []bool{false, true} {
+				t.Run(fmt.Sprintf("Precheck=%t", precheck), func(t *testing.T) {
+					t.Parallel()
+					// Request-controlled resource and delegation hints must have no
+					// effect, whether or not server-owned delegation is present.
+					req := httptest.NewRequest(http.MethodGet, "https://untrusted.example.com/api/v2/users/me?resource="+url.QueryEscape(reports), nil)
+					req.Header.Set("X-Coder-API-Key-Delegation", key.ID)
+					req.Header.Set("X-Coder-MCP-Delegation", "true")
+					req.Header.Set("X-Forwarded-Uri", "/reports")
+					req.Header.Set("X-Forwarded-Host", "coder.example.com")
+					req.Header.Set("Referer", reports)
+					if tc.queryToken {
+						q := req.URL.Query()
+						q.Set("access_token", token)
+						req.URL.RawQuery = q.Encode()
+					} else if !tc.missingToken {
+						req.Header.Set("Authorization", "Bearer "+token)
+					}
+					if tc.delegatedResource != "" {
+						req = req.WithContext(httpmw.WithAPIKeyDelegation(req.Context(), tc.delegatedResource, delegatedID))
+					}
+					originalURL := req.URL.String()
+					handler := httpmw.ExtractAPIKeyMW(httpmw.ExtractAPIKeyConfig{
+						DB: db, AccessURL: origin, Logger: testutil.Logger(t),
+						ResourceURI: tc.resourceURI, ResourceMetadataURL: metadata,
+					})(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+						assert.Equal(t, originalURL, r.URL.String())
+						assert.Equal(t, key.ID, httpmw.APIKey(r).ID)
+						actor := httpmw.UserAuthorization(r.Context())
+						assert.Equal(t, user.ID.String(), actor.ID)
+						assert.Equal(t, key.ScopeSet(), actor.Scope)
+						w.WriteHeader(http.StatusNoContent)
+					}))
+					if precheck {
+						handler = httpmw.PrecheckAPIKey(httpmw.ValidateAPIKeyConfig{DB: db, Logger: testutil.Logger(t)})(handler)
+					}
+					rw := httptest.NewRecorder()
+					handler.ServeHTTP(rw, req)
+					require.Equal(t, tc.status, rw.Code)
+					if tc.wrongKey {
+						var response codersdk.Response
+						require.NoError(t, json.NewDecoder(rw.Body).Decode(&response))
+						require.Equal(t, "Delegated requests must use the credential that authenticated the originating request.", response.Message)
+						require.NotContains(t, response.Message, key.ID)
+						require.NotContains(t, response.Message, delegatedID)
+						require.NotContains(t, rw.Header().Get("WWW-Authenticate"), "expired")
+					}
+					require.Equal(t, originalURL, req.URL.String())
+					if tc.status != http.StatusNoContent {
+						require.Contains(t, rw.Header().Get("WWW-Authenticate"), `resource_metadata="`+metadata+`"`)
+					}
+				})
+			}
+		})
+	}
+}
+
 func randomAPIKeyParts() (id string, secret string, hashedSecret []byte) {
 	id, _ = cryptorand.String(10)
 	secret, hashedSecret, _ = apikey.GenerateSecret(22)
diff --git a/coderd/httpmw/httpmw_internal_test.go b/coderd/httpmw/httpmw_internal_test.go
index bf10f26551..7c99500e47 100644
--- a/coderd/httpmw/httpmw_internal_test.go
+++ b/coderd/httpmw/httpmw_internal_test.go
@@ -5,6 +5,7 @@ import (
 	"encoding/json"
 	"net/http"
 	"net/http/httptest"
+	"net/url"
 	"testing"
 
 	"github.com/go-chi/chi/v5"
@@ -209,7 +210,51 @@ func TestNormalizePathSegments(t *testing.T) {
 	}
 }
 
-// TestExtractExpectedAudience tests audience extraction from HTTP requests
+func TestBuildWWWAuthenticateHeaderResourceMetadata(t *testing.T) {
+	t.Parallel()
+
+	accessURL, err := url.Parse("https://coder.example.com")
+	require.NoError(t, err)
+	for _, tc := range []struct {
+		path        string
+		metadataURL string
+		expectedURL string
+	}{
+		{path: "/api/experimental/mcp/http"},
+		{path: "/api/experimental/mcp/http/"},
+		{path: "/api/experimental/mcp/http/child"},
+		{path: "/api/experimental/mcp/http?toolset=chatgpt"},
+		{path: "/api/experimental/mcp/http-extra"},
+		{path: "/api/v2/users/me"},
+		{
+			path: "/reports", metadataURL: "https://discovery.example.com/reports",
+			expectedURL: "https://discovery.example.com/reports",
+		},
+		{
+			path: "/reports/", metadataURL: "https://discovery.example.com/reports/",
+			expectedURL: "https://discovery.example.com/reports/",
+		},
+		{
+			path: "/reports?resource_metadata=https://untrusted.example.com", metadataURL: "https://discovery.example.com/reports",
+			expectedURL: "https://discovery.example.com/reports",
+		},
+	} {
+		t.Run(tc.path, func(t *testing.T) {
+			t.Parallel()
+			req := httptest.NewRequest(http.MethodPost, "https://untrusted.example.com"+tc.path, nil)
+			expectedURL := tc.expectedURL
+			if expectedURL == "" {
+				expectedURL = "https://coder.example.com/.well-known/oauth-protected-resource"
+			}
+			for _, code := range []int{http.StatusUnauthorized, http.StatusForbidden} {
+				header := buildWWWAuthenticateHeader(accessURL, tc.metadataURL, req, code, codersdk.Response{})
+				require.Contains(t, header, `resource_metadata="`+expectedURL+`"`)
+			}
+		})
+	}
+}
+
+// TestExtractExpectedAudience tests audience extraction from HTTP requests.
 func TestExtractExpectedAudience(t *testing.T) {
 	t.Parallel()
 
@@ -234,6 +279,27 @@ func TestExtractExpectedAudience(t *testing.T) {
 			path:     "/v1/users",
 			expected: "https://api.example.com/",
 		},
+		{
+			name:     "MCPWithoutOverride",
+			scheme:   "https",
+			host:     "example.com",
+			path:     "/api/experimental/mcp/http",
+			expected: "https://example.com/",
+		},
+		{
+			name:     "MCPWithTrailingSlashWithoutOverride",
+			scheme:   "https",
+			host:     "example.com",
+			path:     "/api/experimental/mcp/http/",
+			expected: "https://example.com/",
+		},
+		{
+			name:     "MCPPrefixLookalike",
+			scheme:   "https",
+			host:     "example.com",
+			path:     "/api/experimental/mcp/http-extra",
+			expected: "https://example.com/",
+		},
 		{
 			name:     "WithPort",
 			scheme:   "http",
@@ -256,6 +322,11 @@ func TestExtractExpectedAudience(t *testing.T) {
 
 			result := extractExpectedAudience(nil, req)
 			assert.Equal(t, tc.expected, result)
+
+			accessURL, err := url.Parse(tc.scheme + "://" + tc.host)
+			require.NoError(t, err)
+			req.Host = "untrusted.example.com"
+			assert.Equal(t, tc.expected, extractExpectedAudience(accessURL, req))
 		})
 	}
 }
diff --git a/coderd/mcp/mcp.go b/coderd/mcp/mcp.go
index d447003137..b909b6b779 100644
--- a/coderd/mcp/mcp.go
+++ b/coderd/mcp/mcp.go
@@ -22,8 +22,8 @@ const (
 	// MCPServerInstructions is the instructions text for the MCP server.
 	MCPServerInstructions = "Coder MCP Server providing workspace and template management tools"
 
-	// Used in tests and aibridge.
-	MCPEndpoint = "/api/experimental/mcp/http"
+	// MCPEndpoint is the remote MCP HTTP endpoint path.
+	MCPEndpoint = codersdk.MCPEndpoint
 )
 
 // Server represents an MCP HTTP server instance
diff --git a/coderd/mcp/mcp_e2e_test.go b/coderd/mcp/mcp_e2e_test.go
index c4b306e698..03bb9f303a 100644
--- a/coderd/mcp/mcp_e2e_test.go
+++ b/coderd/mcp/mcp_e2e_test.go
@@ -3,6 +3,7 @@ package mcp_test
 import (
 	"context"
 	"crypto/sha256"
+	"database/sql"
 	"encoding/base64"
 	"encoding/json"
 	"fmt"
@@ -15,6 +16,7 @@ import (
 	"sync/atomic"
 	"testing"
 
+	"github.com/go-chi/chi/v5"
 	"github.com/google/uuid"
 	"github.com/modelcontextprotocol/go-sdk/mcp"
 	"github.com/spf13/afero"
@@ -27,6 +29,8 @@ import (
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/dbfake"
+	"github.com/coder/coder/v2/coderd/database/dbgen"
+	"github.com/coder/coder/v2/coderd/database/dbtestutil"
 	mcpserver "github.com/coder/coder/v2/coderd/mcp"
 	"github.com/coder/coder/v2/coderd/oauth2provider/oauth2providertest"
 	"github.com/coder/coder/v2/coderd/rbac"
@@ -170,6 +174,118 @@ func TestMCPHTTP_E2E_ClientIntegration(t *testing.T) {
 	}
 }
 
+func TestMCPHTTP_E2E_CancelLogStream(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+	db, _ := dbtestutil.NewDB(t)
+	logsDB := &mcpLogStreamStore{Store: db, queried: make(chan struct{}, 1)}
+	outerDone := make(chan struct{})
+	type outerContextKey struct{}
+	coderClient, closer, api := coderdtest.NewWithAPI(t, &coderdtest.Options{
+		Database:         logsDB,
+		DeploymentValues: mcpDeploymentValues(t),
+		APIMiddleware: func(next http.Handler) http.Handler {
+			return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+				if r.URL.Path == mcpserver.MCPEndpoint {
+					defer close(outerDone)
+					r = r.WithContext(context.WithValue(r.Context(), outerContextKey{}, "outer-request-state"))
+				}
+				next.ServeHTTP(w, r)
+			})
+		},
+	})
+	t.Cleanup(func() { _ = closer.Close() })
+	user := coderdtest.CreateFirstUser(t, coderClient)
+	build := dbfake.WorkspaceBuild(t, api.Database, database.WorkspaceTable{
+		OrganizationID: user.OrganizationID, OwnerID: user.UserID,
+	}).Starting().Do().Build
+	key, token := dbgen.APIKey(t, api.Database, database.APIKey{
+		UserID: user.UserID, LoginType: database.LoginTypeOAuth2ProviderApp,
+	})
+	app := dbgen.OAuth2ProviderApp(t, api.Database, database.OAuth2ProviderApp{})
+	dbgen.OAuth2ProviderAppToken(t, api.Database, database.OAuth2ProviderAppToken{
+		AppID: app.ID, UserID: user.UserID, APIKeyID: key.ID,
+		Audience: sql.NullString{String: api.AccessURL.String() + mcpserver.MCPEndpoint, Valid: true},
+	})
+
+	innerDone := make(chan struct{})
+	cancelInner := make(chan context.CancelFunc, 1)
+	root := api.RootHandler
+	api.RootHandler = chi.NewRouter()
+	api.RootHandler.Use(func(next http.Handler) http.Handler {
+		return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			if r.URL.Path == fmt.Sprintf("/api/v2/workspacebuilds/%s/logs", build.ID) {
+				defer close(innerDone)
+				assert.Nil(t, r.Context().Value(outerContextKey{}), "outer request values must not reach internal authentication")
+				// Allow cleanup to release the log follower even if the
+				// cancellation regression fails.
+				innerCtx, cancel := context.WithCancel(r.Context())
+				defer cancel()
+				cancelInner <- cancel
+				r = r.WithContext(innerCtx)
+			}
+			next.ServeHTTP(w, r)
+		})
+	})
+	api.RootHandler.Mount("/", root)
+	t.Cleanup(func() {
+		select {
+		case cancel := <-cancelInner:
+			cancel()
+		default:
+		}
+	})
+
+	// Send a raw stateless MCP call so canceling it disconnects the HTTP
+	// request without an SDK cancellation notification masking the leak.
+	body, err := json.Marshal(map[string]any{
+		"jsonrpc": "2.0", "id": 1, "method": "tools/call",
+		"params": map[string]any{
+			"name":      toolsdk.ToolNameGetWorkspaceBuildLogs,
+			"arguments": map[string]any{"workspace_build_id": build.ID.String()},
+		},
+	})
+	require.NoError(t, err)
+	requestCtx, cancel := context.WithCancel(ctx)
+	defer cancel()
+	req, err := http.NewRequestWithContext(requestCtx, http.MethodPost, api.AccessURL.String()+mcpserver.MCPEndpoint, strings.NewReader(string(body)))
+	require.NoError(t, err)
+	req.Header.Set("Authorization", "Bearer "+token)
+	req.Header.Set("Content-Type", "application/json")
+	req.Header.Set("Accept", "application/json, text/event-stream")
+	req.Header.Set("MCP-Protocol-Version", "2025-03-26")
+	requestDone := make(chan error, 1)
+	go func() {
+		resp, err := coderClient.HTTPClient.Do(req)
+		if resp != nil {
+			_ = resp.Body.Close()
+		}
+		requestDone <- err
+	}()
+
+	// The log query runs after WebSocket acceptance and pubsub subscription.
+	testutil.TryReceive(ctx, t, logsDB.queried)
+	cancel()
+	require.ErrorIs(t, testutil.TryReceive(ctx, t, requestDone), context.Canceled)
+	waitCtx := testutil.Context(t, testutil.WaitShort)
+	testutil.TryReceive(waitCtx, t, innerDone)
+	testutil.TryReceive(waitCtx, t, outerDone)
+}
+
+type mcpLogStreamStore struct {
+	database.Store
+	queried chan struct{}
+}
+
+func (s *mcpLogStreamStore) GetProvisionerLogsAfterID(ctx context.Context, params database.GetProvisionerLogsAfterIDParams) ([]database.ProvisionerJobLog, error) {
+	logs, err := s.Store.GetProvisionerLogsAfterID(ctx, params)
+	select {
+	case s.queried <- struct{}{}:
+	default:
+	}
+	return logs, err
+}
+
 func TestMCPHTTP_E2E_UnauthenticatedAccess(t *testing.T) {
 	t.Parallel()
 
@@ -198,12 +314,120 @@ func TestMCPHTTP_E2E_UnauthenticatedAccess(t *testing.T) {
 
 	// Verify we get 401 Unauthorized
 	require.Equal(t, http.StatusUnauthorized, resp.StatusCode, "Should get HTTP 401 for unauthenticated access")
+	require.Contains(t, resp.Header.Get("WWW-Authenticate"), "Bearer ")
+	require.Contains(t, resp.Header.Get("WWW-Authenticate"), fmt.Sprintf(`resource_metadata=%q`,
+		api.AccessURL.String()+"/.well-known/oauth-protected-resource"+mcpserver.MCPEndpoint))
+	require.Empty(t, resp.Header.Get("Location"))
 
 	// Also test with MCP client to ensure it handles the error gracefully
 	_, err = newIsolatedMCPClient(ctx, mcpURL, "test-client-unauth", nil)
 	require.Error(t, err, "Should fail during MCP initialization without authentication")
 }
 
+func TestMCPHTTP_E2E_ResourcePaths(t *testing.T) {
+	t.Parallel()
+	client := coderdtest.New(t, &coderdtest.Options{DeploymentValues: mcpDeploymentValues(t)})
+	coderdtest.CreateFirstUser(t, client)
+	type credential struct {
+		name       string
+		token      string
+		wantStatus int
+	}
+	tokens := []credential{
+		{name: "Unauthenticated", wantStatus: http.StatusUnauthorized},
+		{name: "SessionToken", token: client.SessionToken(), wantStatus: http.StatusOK},
+	}
+	httpClient := &http.Client{CheckRedirect: func(*http.Request, []*http.Request) error { return http.ErrUseLastResponse }}
+	for _, resource := range []struct {
+		name       string
+		audience   string
+		wantStatus int
+	}{
+		{name: "RootAudience", audience: client.URL.String(), wantStatus: http.StatusForbidden},
+		{name: "MCPAudience", audience: client.URL.String() + mcpserver.MCPEndpoint, wantStatus: http.StatusOK},
+	} {
+		app, secret := oauth2providertest.CreateTestOAuth2App(t, client)
+		verifier, challenge := oauth2providertest.GeneratePKCE(t)
+		code := oauth2providertest.AuthorizeOAuth2App(t, client, client.URL.String(), oauth2providertest.AuthorizeParams{
+			ClientID: app.ID.String(), ResponseType: "code", RedirectURI: oauth2providertest.TestRedirectURI,
+			State: oauth2providertest.GenerateState(t), CodeChallenge: challenge, CodeChallengeMethod: "S256",
+			Resource: resource.audience,
+		})
+		token := oauth2providertest.ExchangeCodeForToken(t, client.URL.String(), oauth2providertest.TokenExchangeParams{
+			GrantType: "authorization_code", Code: code, ClientID: app.ID.String(), ClientSecret: secret,
+			RedirectURI: oauth2providertest.TestRedirectURI, CodeVerifier: verifier, Resource: resource.audience,
+		})
+		tokens = append(tokens, credential{name: resource.name, token: token.AccessToken, wantStatus: resource.wantStatus})
+	}
+	for _, path := range []string{
+		"/api//experimental/mcp/http", "/api/experimental//mcp/http",
+		"/api/experimental/mcp//http", "/api/experimental/mcp/http//",
+		"/api/experimental/mcp/http/child", "/api/experimental/mcp/http/../http",
+		"/api/experimental/mcp/%68ttp", "/api/experimental/mcp/http%2f",
+	} {
+		t.Run(path, func(t *testing.T) {
+			t.Parallel()
+			for _, token := range tokens {
+				t.Run(token.name, func(t *testing.T) {
+					t.Parallel()
+					req, err := http.NewRequestWithContext(t.Context(), http.MethodPost, client.URL.String()+path,
+						strings.NewReader(`{"jsonrpc":"2.0","id":1,"method":"tools/list","params":{}}`))
+					require.NoError(t, err)
+					req.Header.Set("Content-Type", "application/json")
+					req.Header.Set("Accept", "application/json, text/event-stream")
+					if token.token != "" {
+						req.Header.Set("Authorization", "Bearer "+token.token)
+					}
+					resp, err := httpClient.Do(req)
+					require.NoError(t, err)
+					_ = resp.Body.Close()
+					require.Equal(t, http.StatusNotFound, resp.StatusCode)
+					require.Empty(t, resp.Header.Get("WWW-Authenticate"))
+				})
+			}
+		})
+	}
+	t.Run("CanonicalPaths", func(t *testing.T) {
+		t.Parallel()
+		for _, path := range []string{mcpserver.MCPEndpoint, mcpserver.MCPEndpoint + "/"} {
+			for _, token := range tokens {
+				t.Run(path+"/"+token.name, func(t *testing.T) {
+					t.Parallel()
+					req, err := http.NewRequestWithContext(t.Context(), http.MethodPost, client.URL.String()+path,
+						strings.NewReader(`{"jsonrpc":"2.0","id":1,"method":"tools/list","params":{}}`))
+					require.NoError(t, err)
+					req.Header.Set("Content-Type", "application/json")
+					req.Header.Set("Accept", "application/json, text/event-stream")
+					if token.token != "" {
+						req.Header.Set("Authorization", "Bearer "+token.token)
+					}
+					resp, err := httpClient.Do(req)
+					require.NoError(t, err)
+					_ = resp.Body.Close()
+					require.Equal(t, token.wantStatus, resp.StatusCode)
+					if token.wantStatus == http.StatusUnauthorized {
+						metadataURL := client.URL.String() + "/.well-known/oauth-protected-resource" + path
+						require.Contains(t, resp.Header.Get("WWW-Authenticate"), fmt.Sprintf(`resource_metadata=%q`, metadataURL))
+						var metadata codersdk.OAuth2ProtectedResourceMetadata
+						testutil.RequireEventuallyResponseOK(testutil.Context(t, testutil.WaitLong), t, metadataURL, &metadata)
+						require.Equal(t, client.URL.String()+path, metadata.Resource)
+					}
+				})
+			}
+		}
+	})
+	t.Run("CallbackStillRequiresAuthentication", func(t *testing.T) {
+		t.Parallel()
+		req, err := http.NewRequestWithContext(t.Context(), http.MethodGet,
+			client.URL.String()+"/api/experimental/mcp/servers/"+uuid.NewString()+"/oauth2/callback", nil)
+		require.NoError(t, err)
+		resp, err := httpClient.Do(req)
+		require.NoError(t, err)
+		defer resp.Body.Close()
+		require.Equal(t, http.StatusUnauthorized, resp.StatusCode)
+	})
+}
+
 func TestMCPHTTP_E2E_ToolWithWorkspace(t *testing.T) {
 	t.Parallel()
 
@@ -520,6 +744,205 @@ func TestMCPHTTP_E2E_OAuth2_EndToEnd(t *testing.T) {
 		t.Logf("OAuth2 Bearer token MCP test successful: Found %d tools", len(tools.Tools))
 	})
 
+	t.Run("PathQualifiedResource", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitLong)
+		mcpURL := api.AccessURL.String() + mcpserver.MCPEndpoint
+		app, secret := oauth2providertest.CreateTestOAuth2App(t, coderClient)
+		verifier, challenge := oauth2providertest.GeneratePKCE(t)
+		code := oauth2providertest.AuthorizeOAuth2App(t, coderClient, api.AccessURL.String(), oauth2providertest.AuthorizeParams{
+			ClientID: app.ID.String(), ResponseType: "code",
+			RedirectURI:   oauth2providertest.TestRedirectURI,
+			State:         oauth2providertest.GenerateState(t),
+			CodeChallenge: challenge, CodeChallengeMethod: "S256",
+			Resource: mcpURL,
+		})
+		token := oauth2providertest.ExchangeCodeForToken(t, api.AccessURL.String(), oauth2providertest.TokenExchangeParams{
+			GrantType: "authorization_code", Code: code,
+			ClientID: app.ID.String(), ClientSecret: secret,
+			RedirectURI:  oauth2providertest.TestRedirectURI,
+			CodeVerifier: verifier, Resource: mcpURL,
+		})
+		mcpClient, err := newIsolatedMCPClient(ctx, mcpURL, "path-resource-client", map[string]string{
+			"Authorization": "Bearer " + token.AccessToken,
+		})
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = mcpClient.Close() })
+		require.Equal(t, mcpserver.MCPServerName, mcpClient.InitializeResult().ServerInfo.Name)
+		tools, err := mcpClient.ListTools(ctx, nil)
+		require.NoError(t, err)
+		require.NotEmpty(t, tools.Tools)
+
+		result, err := mcpClient.CallTool(ctx, &mcp.CallToolParams{
+			Name: toolsdk.ToolNameGetAuthenticatedUser,
+		})
+		require.NoError(t, err)
+		require.False(t, result.IsError, "REST-backed tool failed: %+v", result.Content)
+		require.Len(t, result.Content, 1)
+		text, ok := result.Content[0].(*mcp.TextContent)
+		require.True(t, ok)
+		var user codersdk.User
+		require.NoError(t, json.Unmarshal([]byte(text.Text), &user))
+		me, err := coderClient.User(ctx, codersdk.Me)
+		require.NoError(t, err)
+		require.Equal(t, me.ID, user.ID)
+
+		// Exercise SDK URL construction through the delegated transport. A
+		// workspace owner must not select the token-creation endpoint.
+		before, err := coderClient.Tokens(ctx, codersdk.Me, codersdk.TokensFilter{})
+		require.NoError(t, err)
+		for _, injectedUser := range []string{
+			"me/keys/tokens?", "me/keys/tokens#", "me/keys/tokens/../tokens?",
+			"me%2fkeys%2ftokens%3f", "../users/me/keys/tokens?", ".", "..",
+		} {
+			result, err := mcpClient.CallTool(ctx, &mcp.CallToolParams{
+				Name: toolsdk.ToolNameCreateWorkspace,
+				Arguments: map[string]any{
+					"user": injectedUser, "name": "unused",
+					"template_id": uuid.NewString(), "rich_parameters": map[string]string{},
+				},
+			})
+			require.NoError(t, err)
+			assert.True(t, result.IsError, "injected owner %q must fail", injectedUser)
+			require.Len(t, result.Content, 1)
+			text, ok := result.Content[0].(*mcp.TextContent)
+			require.True(t, ok)
+			assert.Contains(t, text.Text, "invalid user")
+			after, err := coderClient.Tokens(ctx, codersdk.Me, codersdk.TokensFilter{})
+			require.NoError(t, err)
+			require.ElementsMatch(t, before, after, "workspace tool must not create API keys")
+		}
+
+		req, err := http.NewRequestWithContext(ctx, http.MethodGet, api.AccessURL.String()+"/api/v2/users/me", nil)
+		require.NoError(t, err)
+		req.Header.Set("Authorization", "Bearer "+token.AccessToken)
+		// Neither a claimed origin nor a delegation-looking header may
+		// turn an external REST request into trusted MCP work.
+		req.Header.Set("X-Coder-MCP-Delegation", "true")
+		req.Header.Set("X-Forwarded-Uri", mcpserver.MCPEndpoint)
+		req.Header.Set("Referer", mcpURL)
+		resp, err := http.DefaultClient.Do(req)
+		require.NoError(t, err)
+		defer resp.Body.Close()
+		require.Equal(t, http.StatusForbidden, resp.StatusCode)
+		var response codersdk.Response
+		require.NoError(t, json.NewDecoder(resp.Body).Decode(&response))
+		require.Equal(t, "Token audience validation failed", response.Message)
+
+		refreshed := oauth2providertest.ExchangeCodeForToken(t, api.AccessURL.String(), oauth2providertest.TokenExchangeParams{
+			GrantType: "refresh_token", RefreshToken: token.RefreshToken,
+			ClientID: app.ID.String(), ClientSecret: secret, Resource: mcpURL,
+		})
+		refreshedClient, err := newIsolatedMCPClient(ctx, mcpURL, "refreshed-path-resource", map[string]string{
+			"Authorization": "Bearer " + refreshed.AccessToken,
+		})
+		require.NoError(t, err)
+		t.Cleanup(func() { _ = refreshedClient.Close() })
+		result, err = refreshedClient.CallTool(ctx, &mcp.CallToolParams{Name: toolsdk.ToolNameGetAuthenticatedUser})
+		require.NoError(t, err)
+		require.False(t, result.IsError)
+		require.NoError(t, coderClient.RevokeOAuth2Token(ctx, app.ID, secret, refreshed.AccessToken))
+		_, err = refreshedClient.CallTool(ctx, &mcp.CallToolParams{Name: toolsdk.ToolNameGetAuthenticatedUser})
+		require.Error(t, err, "revoked token must not execute tools")
+	})
+
+	t.Run("PathQualifiedAuthorization", func(t *testing.T) {
+		t.Parallel()
+		ctx := testutil.Context(t, testutil.WaitLong)
+		me, err := coderClient.User(ctx, codersdk.Me)
+		require.NoError(t, err)
+		orgID := me.OrganizationIDs[0]
+		memberClient, member := coderdtest.CreateAnotherUser(t, coderClient, orgID)
+		orgAdminClient, orgAdmin := coderdtest.CreateAnotherUser(t, coderClient, orgID, rbac.ScopedRoleOrgAdmin(orgID))
+		otherOrg := dbgen.Organization(t, api.Database, database.Organization{})
+		ownWorkspace := dbfake.WorkspaceBuild(t, api.Database, database.WorkspaceTable{
+			OrganizationID: orgID, OwnerID: member.ID,
+		}).Do().Workspace
+		peerWorkspace := dbfake.WorkspaceBuild(t, api.Database, database.WorkspaceTable{
+			OrganizationID: orgID, OwnerID: me.ID,
+		}).Do().Workspace
+		otherOrgWorkspace := dbfake.WorkspaceBuild(t, api.Database, database.WorkspaceTable{
+			OrganizationID: otherOrg.ID, OwnerID: me.ID,
+		}).Do().Workspace
+
+		for _, tc := range []struct {
+			name        string
+			client      *codersdk.Client
+			userID      uuid.UUID
+			scope       string
+			ownAllowed  bool
+			peerAllowed bool
+		}{
+			{name: "Member", client: memberClient, userID: member.ID, scope: "coder:all", ownAllowed: true},
+			{name: "OrganizationAdmin", client: orgAdminClient, userID: orgAdmin.ID, scope: "coder:all", ownAllowed: true, peerAllowed: true},
+			{name: "UserReadOnlyScope", client: memberClient, userID: member.ID, scope: "user:read"},
+			{name: "OwnerReadOnlyScope", client: coderClient, userID: me.ID, scope: "user:read"},
+		} {
+			t.Run(tc.name, func(t *testing.T) {
+				t.Parallel()
+				ctx := testutil.Context(t, testutil.WaitLong)
+				mcpURL := api.AccessURL.String() + mcpserver.MCPEndpoint
+				app, secret := oauth2providertest.CreateTestOAuth2App(t, coderClient)
+				verifier, challenge := oauth2providertest.GeneratePKCE(t)
+				code := oauth2providertest.AuthorizeOAuth2App(t, tc.client, api.AccessURL.String(), oauth2providertest.AuthorizeParams{
+					ClientID: app.ID.String(), ResponseType: "code",
+					RedirectURI: oauth2providertest.TestRedirectURI, State: oauth2providertest.GenerateState(t),
+					CodeChallenge: challenge, CodeChallengeMethod: "S256", Resource: mcpURL, Scope: tc.scope,
+				})
+				token := oauth2providertest.ExchangeCodeForToken(t, api.AccessURL.String(), oauth2providertest.TokenExchangeParams{
+					GrantType: "authorization_code", Code: code, ClientID: app.ID.String(), ClientSecret: secret,
+					RedirectURI: oauth2providertest.TestRedirectURI, CodeVerifier: verifier, Resource: mcpURL,
+				})
+				client, err := newIsolatedMCPClient(ctx, mcpURL, tc.name, map[string]string{
+					"Authorization": "Bearer " + token.AccessToken,
+				})
+				require.NoError(t, err)
+				t.Cleanup(func() { _ = client.Close() })
+				result, err := client.CallTool(ctx, &mcp.CallToolParams{Name: toolsdk.ToolNameGetAuthenticatedUser})
+				require.NoError(t, err)
+				require.False(t, result.IsError)
+				var user codersdk.User
+				require.NoError(t, json.Unmarshal([]byte(result.Content[0].(*mcp.TextContent).Text), &user))
+				require.Equal(t, tc.userID, user.ID)
+
+				if tc.scope == "user:read" {
+					visible, err := tc.client.Workspaces(ctx, codersdk.WorkspaceFilter{Owner: "me"})
+					require.NoError(t, err)
+					require.NotEmpty(t, visible.Workspaces, "unrestricted credential must see fixture workspaces")
+					result, err := client.CallTool(ctx, &mcp.CallToolParams{Name: toolsdk.ToolNameListWorkspaces})
+					require.NoError(t, err)
+					require.False(t, result.IsError)
+					var workspaces []toolsdk.MinimalWorkspace
+					require.NoError(t, json.Unmarshal([]byte(result.Content[0].(*mcp.TextContent).Text), &workspaces))
+					require.Empty(t, workspaces, "OAuth scope must filter workspace visibility even for an Owner")
+				}
+
+				for _, ws := range []struct {
+					id      uuid.UUID
+					allowed bool
+				}{
+					{id: ownWorkspace.ID, allowed: tc.ownAllowed},
+					{id: peerWorkspace.ID, allowed: tc.peerAllowed},
+					{id: otherOrgWorkspace.ID},
+				} {
+					result, err := client.CallTool(ctx, &mcp.CallToolParams{
+						Name: toolsdk.ToolNameGetWorkspace, Arguments: map[string]any{"workspace_id": ws.id.String()},
+					})
+					require.NoError(t, err)
+					require.Equal(t, !ws.allowed, result.IsError)
+					text := result.Content[0].(*mcp.TextContent).Text
+					if ws.allowed {
+						var workspace codersdk.Workspace
+						require.NoError(t, json.Unmarshal([]byte(text), &workspace))
+						require.Equal(t, ws.id, workspace.ID)
+					} else {
+						require.Contains(t, text, "404", "must fail RBAC, not audience validation")
+					}
+				}
+			})
+		}
+	})
+
 	// Test 3: Full OAuth2 Authorization Code Flow with Token Refresh
 	t.Run("OAuth2FullFlowWithTokenRefresh", func(t *testing.T) {
 		t.Parallel()
diff --git a/coderd/mcp_http.go b/coderd/mcp_http.go
index 0c0fb75765..d3cf8b4003 100644
--- a/coderd/mcp_http.go
+++ b/coderd/mcp_http.go
@@ -39,9 +39,17 @@ func (api *API) mcpHTTPHandler() http.Handler {
 			})
 			return
 		}
-		// Extract the original session token from the request
+		// Keep tool requests in-process. The private transport carries the
+		// originating MCP audience without granting external REST access.
+		transport, closeTransport := newMCPDelegatedTransport(api.Logger, api.RootHandler, api.AccessURL, httpmw.APIKey(r).ID)
+		defer closeTransport()
+		// The MCP SDK detaches tool cancellation and waits for in-flight tools
+		// before returning, so close their transport independently on disconnect.
+		stopClose := context.AfterFunc(r.Context(), closeTransport)
+		defer stopClose()
 		authenticatedClient := codersdk.New(api.AccessURL,
-			codersdk.WithSessionToken(httpmw.APITokenFromRequest(r)))
+			codersdk.WithSessionToken(httpmw.APITokenFromRequest(r)),
+			codersdk.WithHTTPClient(&http.Client{Transport: transport}))
 
 		// Wrap the agent connection function to enforce ActionSSH
 		// on the workspace. Without this check, a user who can read
diff --git a/coderd/mcp_transport.go b/coderd/mcp_transport.go
new file mode 100644
index 0000000000..edd2dcfb29
--- /dev/null
+++ b/coderd/mcp_transport.go
@@ -0,0 +1,138 @@
+package coderd
+
+import (
+	"context"
+	"net"
+	"net/http"
+	"net/url"
+	"path"
+	"strings"
+	"sync"
+	"time"
+
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog/v3"
+	"github.com/coder/coder/v2/coderd/httpmw"
+	"github.com/coder/coder/v2/coderd/mcp"
+)
+
+// mcpDelegatedReadHeaderTimeout bounds header reads on the in-process delegation
+// server to satisfy gosec G112. The only client is the local net.Pipe transport,
+// so this is not tuned for a slow network client.
+const mcpDelegatedReadHeaderTimeout = 10 * time.Second
+
+// newMCPDelegatedTransport delegates same-origin REST requests over net.Pipe,
+// preserving streaming and WebSockets without inheriting caller context values.
+// Middleware revalidates the original credential, binds it to apiKeyID, and
+// checks its MCP audience. Call cleanup to release the server and connections.
+func newMCPDelegatedTransport(logger slog.Logger, handler http.Handler, accessURL *url.URL, apiKeyID string) (http.RoundTripper, func()) {
+	ctx, cancel := context.WithCancel(context.Background())
+	listener := &mcpListener{ctx: ctx, cancel: cancel, connections: make(chan net.Conn)}
+	server := &http.Server{
+		Handler:           handler,
+		ReadHeaderTimeout: mcpDelegatedReadHeaderTimeout,
+		// Pipe connections carry no TLS, so net/http errors here are handler
+		// faults; route them to the Coder logger instead of stderr.
+		ErrorLog: slog.Stdlib(ctx, logger.Named("mcp_delegated_transport"), slog.LevelError),
+		BaseContext: func(net.Listener) context.Context {
+			return httpmw.WithAPIKeyDelegation(ctx, accessURL.JoinPath(mcp.MCPEndpoint).String(), apiKeyID)
+		},
+	}
+	done := make(chan struct{})
+	go func() {
+		defer close(done)
+		_ = server.Serve(listener)
+	}()
+	transport := &http.Transport{DialContext: listener.dialContext}
+	return &mcpDelegatedTransport{origin: *accessURL, transport: transport}, sync.OnceFunc(func() {
+		cancel()
+		transport.CloseIdleConnections()
+		_ = server.Close()
+		<-done
+	})
+}
+
+type mcpDelegatedTransport struct {
+	origin    url.URL
+	transport *http.Transport
+}
+
+func (t *mcpDelegatedTransport) RoundTrip(req *http.Request) (*http.Response, error) {
+	reject := func(message string) (*http.Response, error) {
+		if req.Body != nil {
+			_ = req.Body.Close()
+		}
+		return nil, xerrors.New(message)
+	}
+	// Reject other origins, including redirect targets, so the bearer token
+	// never leaves the process.
+	if req.URL.Scheme != t.origin.Scheme || req.URL.Host != t.origin.Host || req.Host != t.origin.Host || req.URL.User != nil {
+		return reject("MCP tool request must target the Coder deployment")
+	}
+	if err := validateMCPDelegatedPath(req.URL.Path); err != nil {
+		return reject(err.Error())
+	}
+	clone := req.Clone(req.Context())
+	// Even for HTTPS deployments, these bytes only travel over net.Pipe.
+	clone.URL.Scheme = "http"
+	return t.transport.RoundTrip(clone)
+}
+
+func validateMCPDelegatedPath(requestPath string) error {
+	// Reject aliases before routing can normalize them into another endpoint.
+	if path.Clean(requestPath) != strings.TrimSuffix(requestPath, "/") {
+		return xerrors.New("MCP tool request must use a canonical REST path")
+	}
+	if (!strings.HasPrefix(requestPath, "/api/v2/") && !strings.HasPrefix(requestPath, "/api/experimental/")) ||
+		strings.HasPrefix(requestPath, "/api/experimental/mcp/") {
+		return xerrors.New("MCP tool request must target an internal REST endpoint")
+	}
+	return nil
+}
+
+type mcpListener struct {
+	ctx         context.Context
+	cancel      context.CancelFunc
+	connections chan net.Conn
+}
+
+func (l *mcpListener) dialContext(ctx context.Context, _, _ string) (net.Conn, error) {
+	client, server := net.Pipe()
+	// Closing the MCP transport also closes hijacked WebSocket connections,
+	// which http.Server.Close does not own after the upgrade.
+	context.AfterFunc(l.ctx, func() {
+		_ = client.Close()
+		_ = server.Close()
+	})
+	select {
+	case <-ctx.Done():
+		_ = client.Close()
+		_ = server.Close()
+		return nil, ctx.Err()
+	case <-l.ctx.Done():
+		_ = client.Close()
+		_ = server.Close()
+		return nil, net.ErrClosed
+	case l.connections <- server:
+		return client, nil
+	}
+}
+
+func (l *mcpListener) Accept() (net.Conn, error) {
+	select {
+	case <-l.ctx.Done():
+		return nil, net.ErrClosed
+	case conn := <-l.connections:
+		return conn, nil
+	}
+}
+
+func (l *mcpListener) Close() error {
+	l.cancel()
+	return nil
+}
+
+func (*mcpListener) Addr() net.Addr {
+	return &net.TCPAddr{IP: net.IPv4(127, 0, 0, 1)}
+}
diff --git a/coderd/mcp_transport_bench_internal_test.go b/coderd/mcp_transport_bench_internal_test.go
new file mode 100644
index 0000000000..c0f64e9112
--- /dev/null
+++ b/coderd/mcp_transport_bench_internal_test.go
@@ -0,0 +1,149 @@
+package coderd
+
+import (
+	"context"
+	"io"
+	"net/http"
+	"net/http/httptest"
+	"net/url"
+	"runtime"
+	"sync"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/testutil"
+)
+
+// BenchmarkMCPDelegatedTransport isolates transport overhead with a trivial
+// handler, excluding MCP, authentication, database work, and request creation.
+func BenchmarkMCPDelegatedTransport(b *testing.B) {
+	origin := &url.URL{Scheme: "https", Host: "coder.example.com"}
+	req, err := http.NewRequestWithContext(b.Context(), http.MethodGet, origin.String()+"/api/v2/users/me", nil)
+	require.NoError(b, err)
+	logger := testutil.Logger(b)
+	handler := http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
+		w.WriteHeader(http.StatusNoContent)
+	})
+
+	b.Run("Reuse", func(b *testing.B) {
+		transport, closeTransport := newMCPDelegatedTransport(logger, handler, origin, "benchmark-key")
+		defer closeTransport()
+		benchmarkMCPNoContent(b, transport, req)
+		b.ReportAllocs()
+		for b.Loop() {
+			benchmarkMCPNoContent(b, transport, req)
+		}
+	})
+	b.Run("SetupTeardown", func(b *testing.B) {
+		b.ReportAllocs()
+		for b.Loop() {
+			_, closeTransport := newMCPDelegatedTransport(logger, handler, origin, "benchmark-key")
+			closeTransport()
+		}
+	})
+	b.Run("SetupFirstCallTeardown", func(b *testing.B) {
+		b.ReportAllocs()
+		for b.Loop() {
+			func() {
+				transport, closeTransport := newMCPDelegatedTransport(logger, handler, origin, "benchmark-key")
+				defer closeTransport()
+				benchmarkMCPNoContent(b, transport, req)
+			}()
+		}
+	})
+	b.Run("BufferedRecorderBaseline", func(b *testing.B) {
+		// This direct buffered call is not production-equivalent: it has no
+		// streaming, hijacking, HTTP serialization, or delegation isolation.
+		b.ReportAllocs()
+		for b.Loop() {
+			recorder := httptest.NewRecorder()
+			handler.ServeHTTP(recorder, req)
+			resp := recorder.Result()
+			if err := resp.Body.Close(); err != nil {
+				b.Fatal(err)
+			}
+			if resp.StatusCode != http.StatusNoContent {
+				b.Fatalf("unexpected status: %d", resp.StatusCode)
+			}
+		}
+	})
+}
+
+func benchmarkMCPNoContent(b *testing.B, transport http.RoundTripper, req *http.Request) {
+	resp, err := transport.RoundTrip(req)
+	if err != nil {
+		b.Fatal(err)
+	}
+	if err := resp.Body.Close(); err != nil {
+		b.Fatal(err)
+	}
+	if resp.StatusCode != http.StatusNoContent {
+		b.Fatalf("unexpected status: %d", resp.StatusCode)
+	}
+}
+
+// BenchmarkMCPDelegatedTransportActiveStreams measures one cohort per iteration,
+// not per-request latency. Run standalone with -run '^$' -benchtime=1x so global
+// goroutine counts are not obscured by other tests. Each stream owns a transport,
+// modeling separate outer MCP requests rather than one shared connection pool.
+func BenchmarkMCPDelegatedTransportActiveStreams(b *testing.B) {
+	for b.Loop() {
+		benchmarkMCPActiveStreamCohort(b)
+	}
+}
+
+func benchmarkMCPActiveStreamCohort(b *testing.B) {
+	const streams = 1024
+	ctx, cancel := context.WithTimeout(b.Context(), testutil.WaitLong)
+	defer cancel()
+	origin := &url.URL{Scheme: "https", Host: "coder.example.com"}
+	req, err := http.NewRequestWithContext(ctx, http.MethodGet, origin.String()+"/api/v2/logs", nil)
+	require.NoError(b, err)
+	logger := testutil.Logger(b)
+	baseline := runtime.NumGoroutine()
+	completed := make(chan struct{}, streams)
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		defer func() { completed <- struct{}{} }()
+		w.Header().Set("Content-Type", "text/event-stream")
+		_, _ = io.WriteString(w, "data: ready\n\n")
+		w.(http.Flusher).Flush()
+		<-r.Context().Done()
+	})
+	closers := make([]func(), 0, streams)
+	cleanup := sync.OnceFunc(func() {
+		for _, closeTransport := range closers {
+			closeTransport()
+		}
+	})
+	defer cleanup()
+	for range streams {
+		transport, closeTransport := newMCPDelegatedTransport(logger, handler, origin, "benchmark-key")
+		closers = append(closers, closeTransport)
+		//nolint:bodyclose // Bodies are closed with their transports in cleanup.
+		resp, err := transport.RoundTrip(req)
+		require.NoError(b, err)
+		closers[len(closers)-1] = func() {
+			closeTransport()
+			_ = resp.Body.Close()
+		}
+		require.Equal(b, http.StatusOK, resp.StatusCode)
+		var first [len("data: ready\n\n")]byte
+		_, err = io.ReadFull(resp.Body, first[:])
+		require.NoError(b, err)
+	}
+	active := runtime.NumGoroutine()
+	cleanup()
+	for range streams {
+		testutil.TryReceive(ctx, b, completed)
+	}
+	// Connection goroutines can exit after Server.Close returns. Report rather
+	// than assert the process-wide baseline, which unrelated work can change.
+	for runtime.NumGoroutine() > baseline && ctx.Err() == nil {
+		runtime.Gosched()
+	}
+	b.ReportMetric(float64(streams), "streams")
+	b.ReportMetric(float64(baseline), "goroutines-baseline")
+	b.ReportMetric(float64(active), "goroutines-active")
+	b.ReportMetric(float64(runtime.NumGoroutine()), "goroutines-cleaned")
+}
diff --git a/coderd/mcp_transport_internal_test.go b/coderd/mcp_transport_internal_test.go
new file mode 100644
index 0000000000..dbdcd88c4b
--- /dev/null
+++ b/coderd/mcp_transport_internal_test.go
@@ -0,0 +1,227 @@
+package coderd
+
+import (
+	"context"
+	"database/sql"
+	"io"
+	"net/http"
+	"net/url"
+	"strings"
+	"sync/atomic"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/v2/coderd/database"
+	"github.com/coder/coder/v2/coderd/database/dbgen"
+	"github.com/coder/coder/v2/coderd/database/dbtestutil"
+	"github.com/coder/coder/v2/coderd/database/dbtime"
+	"github.com/coder/coder/v2/coderd/httpmw"
+	"github.com/coder/coder/v2/coderd/mcp"
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/testutil"
+	"github.com/coder/websocket"
+)
+
+func TestMCPTransportAuthentication(t *testing.T) {
+	t.Parallel()
+	db, _ := dbtestutil.NewDB(t)
+	user := dbgen.User(t, db, database.User{})
+	app := dbgen.OAuth2ProviderApp(t, db, database.OAuth2ProviderApp{})
+	origin, err := url.Parse("https://coder.example.com")
+	require.NoError(t, err)
+	handler := httpmw.PrecheckAPIKey(httpmw.ValidateAPIKeyConfig{DB: db})(
+		httpmw.ExtractAPIKeyMW(httpmw.ExtractAPIKeyConfig{DB: db, AccessURL: origin, Logger: testutil.Logger(t)})(
+			http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+				assert.Equal(t, user.ID.String(), httpmw.UserAuthorization(r.Context()).ID)
+				w.WriteHeader(http.StatusNoContent)
+			})))
+
+	for _, tc := range []struct {
+		name       string
+		audience   string
+		status     int
+		expired    bool
+		deleted    bool
+		wrongKeyID bool
+	}{
+		{name: "MCPAudience", audience: origin.String() + mcp.MCPEndpoint, status: http.StatusNoContent},
+		{name: "TrailingSlash", audience: origin.String() + mcp.MCPEndpoint + "/", status: http.StatusNoContent},
+		{name: "UnboundLegacyToken", status: http.StatusNoContent},
+		{name: "RootAudience", audience: origin.String(), status: http.StatusForbidden},
+		{name: "OtherDeployment", audience: "https://other.example.com" + mcp.MCPEndpoint, status: http.StatusForbidden},
+		{name: "WrongKey", audience: origin.String() + mcp.MCPEndpoint, wrongKeyID: true, status: http.StatusUnauthorized},
+		{name: "Expired", audience: origin.String() + mcp.MCPEndpoint, expired: true, status: http.StatusUnauthorized},
+		{name: "Deleted", audience: origin.String() + mcp.MCPEndpoint, deleted: true, status: http.StatusUnauthorized},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+			ctx := testutil.Context(t, testutil.WaitLong)
+			key, token := dbgen.APIKey(t, db, database.APIKey{UserID: user.ID, LoginType: database.LoginTypeOAuth2ProviderApp})
+			dbgen.OAuth2ProviderAppToken(t, db, database.OAuth2ProviderAppToken{
+				AppID: app.ID, UserID: user.ID, APIKeyID: key.ID, HashPrefix: []byte(key.ID),
+				Audience: sql.NullString{String: tc.audience, Valid: tc.audience != ""},
+			})
+			delegatedID := key.ID
+			if tc.wrongKeyID {
+				delegatedID = "other-key"
+			}
+			transport, closeTransport := newMCPDelegatedTransport(testutil.Logger(t), handler, origin, delegatedID)
+			t.Cleanup(closeTransport)
+			client := codersdk.New(origin, codersdk.WithSessionToken(token), codersdk.WithHTTPClient(&http.Client{Transport: transport}))
+
+			if tc.expired || tc.deleted {
+				// Validate once before mutation, then reuse the same private
+				// transport. Internal calls must not cache authentication.
+				resp, err := client.Request(ctx, http.MethodGet, "/api/v2/users/me", nil)
+				require.NoError(t, err)
+				require.NoError(t, resp.Body.Close())
+				require.Equal(t, http.StatusNoContent, resp.StatusCode)
+				if tc.deleted {
+					require.NoError(t, db.DeleteAPIKeyByID(ctx, key.ID))
+				} else {
+					require.NoError(t, db.UpdateAPIKeyByID(ctx, database.UpdateAPIKeyByIDParams{
+						ID: key.ID, LastUsed: key.LastUsed, ExpiresAt: dbtime.Now().Add(-time.Hour), IPAddress: key.IPAddress,
+					}))
+				}
+			}
+			resp, err := client.Request(ctx, http.MethodGet, "/api/v2/users/me", nil)
+			require.NoError(t, err)
+			defer resp.Body.Close()
+			require.Equal(t, tc.status, resp.StatusCode)
+		})
+	}
+}
+
+func TestMCPTransportIsolation(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+	origin, err := url.Parse("https://coder.example.com")
+	require.NoError(t, err)
+	type callerContextKey struct{}
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		assert.Nil(t, r.Context().Value(callerContextKey{}), "caller auth and routing state must not cross the connection")
+		if r.URL.Path == "/api/v2/redirect" {
+			http.Redirect(w, r, "https://other.example.com/api/v2/users/me", http.StatusFound)
+			return
+		}
+		w.WriteHeader(http.StatusNoContent)
+	})
+	transport, closeTransport := newMCPDelegatedTransport(testutil.Logger(t), handler, origin, "test-key")
+	t.Cleanup(closeTransport)
+	client := &http.Client{Transport: transport}
+
+	for _, target := range []string{
+		"https://other.example.com/api/v2/users/me",
+		"http://coder.example.com/api/v2/users/me",
+		"https://coder.example.com/oauth2/tokens",
+		"https://coder.example.com/api/experimental/mcp/http",
+		"https://coder.example.com/api/experimental//mcp/http",
+		"https://coder.example.com/api/v2/../../oauth2/tokens",
+		"https://coder.example.com/api/v2/redirect",
+	} {
+		body := &mcpRequestBody{Reader: strings.NewReader("test")}
+		req, err := http.NewRequestWithContext(ctx, http.MethodPost, target, body)
+		require.NoError(t, err)
+		resp, err := client.Do(req)
+		if resp != nil {
+			_ = resp.Body.Close()
+		}
+		require.Error(t, err, "untrusted destination must not be reachable")
+		require.True(t, body.closed.Load(), "rejected request body must be closed")
+	}
+	req, err := http.NewRequestWithContext(context.WithValue(ctx, callerContextKey{}, "outer-auth"), http.MethodGet, origin.String()+"/api/v2/users/me", nil)
+	require.NoError(t, err)
+	resp, err := client.Do(req)
+	require.NoError(t, err)
+	require.NoError(t, resp.Body.Close())
+	require.Equal(t, http.StatusNoContent, resp.StatusCode)
+
+	closeTransport()
+	resp, err = client.Do(req)
+	if resp != nil {
+		_ = resp.Body.Close()
+	}
+	require.Error(t, err, "transport must not outlive its MCP request")
+}
+
+type mcpRequestBody struct {
+	io.Reader
+	closed atomic.Bool
+}
+
+func (b *mcpRequestBody) Close() error {
+	b.closed.Store(true)
+	return nil
+}
+
+func TestMCPTransportStreaming(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+	origin, err := url.Parse("https://coder.example.com")
+	require.NoError(t, err)
+	handlerDone := make(chan struct{})
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		defer close(handlerDone)
+		_, _ = io.WriteString(w, "first\n")
+		w.(http.Flusher).Flush()
+		<-r.Context().Done()
+	})
+	transport, closeTransport := newMCPDelegatedTransport(testutil.Logger(t), handler, origin, "test-key")
+	t.Cleanup(closeTransport)
+	client := &http.Client{Transport: transport}
+	requestCtx, cancel := context.WithCancel(ctx)
+	defer cancel()
+	req, err := http.NewRequestWithContext(requestCtx, http.MethodGet, origin.String()+"/api/v2/logs", nil)
+	require.NoError(t, err)
+	resp, err := client.Do(req)
+	require.NoError(t, err)
+	defer resp.Body.Close()
+	first := make([]byte, len("first\n"))
+	_, err = io.ReadFull(resp.Body, first)
+	require.NoError(t, err)
+	require.Equal(t, "first\n", string(first))
+	cancel()
+	_, err = resp.Body.Read(first)
+	require.Error(t, err)
+	testutil.TryReceive(ctx, t, handlerDone)
+}
+
+func TestMCPTransportWebSocket(t *testing.T) {
+	t.Parallel()
+	ctx := testutil.Context(t, testutil.WaitLong)
+	origin, err := url.Parse("https://coder.example.com")
+	require.NoError(t, err)
+	handlerDone := make(chan struct{})
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		defer close(handlerDone)
+		conn, err := websocket.Accept(w, r, nil)
+		if !assert.NoError(t, err) {
+			return
+		}
+		defer conn.CloseNow()
+		kind, data, err := conn.Read(ctx)
+		if !assert.NoError(t, err) {
+			return
+		}
+		assert.NoError(t, conn.Write(ctx, kind, data))
+		_, _, err = conn.Read(ctx)
+		assert.Error(t, err, "transport cleanup must close hijacked connections")
+	})
+	transport, closeTransport := newMCPDelegatedTransport(testutil.Logger(t), handler, origin, "test-key")
+	t.Cleanup(closeTransport)
+	conn, resp, err := websocket.Dial(ctx, "wss://coder.example.com/api/v2/chats/watch", &websocket.DialOptions{HTTPClient: &http.Client{Transport: transport}})
+	if resp != nil && resp.Body != nil {
+		defer resp.Body.Close()
+	}
+	require.NoError(t, err)
+	defer conn.CloseNow()
+	require.NoError(t, conn.Write(ctx, websocket.MessageText, []byte("ping")))
+	_, data, err := conn.Read(ctx)
+	require.NoError(t, err)
+	require.Equal(t, "ping", string(data))
+	closeTransport()
+	testutil.TryReceive(ctx, t, handlerDone)
+}
diff --git a/coderd/oauth2provider/metadata.go b/coderd/oauth2provider/metadata.go
index 5a98c4c76f..6f3a4bd43c 100644
--- a/coderd/oauth2provider/metadata.go
+++ b/coderd/oauth2provider/metadata.go
@@ -3,6 +3,7 @@ package oauth2provider
 import (
 	"net/http"
 	"net/url"
+	"strings"
 
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/dbauthz"
@@ -51,8 +52,20 @@ func GetAuthorizationServerMetadata(db database.Store, accessURL *url.URL) http.
 func GetProtectedResourceMetadata(accessURL *url.URL) http.HandlerFunc {
 	return func(rw http.ResponseWriter, r *http.Request) {
 		ctx := r.Context()
+		resource := accessURL.String()
+		suffix := strings.TrimPrefix(r.URL.Path, "/.well-known/oauth-protected-resource")
+		switch suffix {
+		case "", "/":
+		case codersdk.MCPEndpoint, codersdk.MCPEndpoint + "/":
+			resource = accessURL.JoinPath(suffix).String()
+		default:
+			// Match before joining paths so malformed or unknown resources
+			// cannot be normalized into a supported resource (RFC 9728 §3.1).
+			httpapi.RouteNotFound(rw)
+			return
+		}
 		metadata := codersdk.OAuth2ProtectedResourceMetadata{
-			Resource:             accessURL.String(),
+			Resource:             resource,
 			AuthorizationServers: []string{accessURL.String()},
 			ScopesSupported:      rbac.ExternalScopeNames(),
 			// RFC 6750 Bearer Token methods supported as fallback methods in api key middleware
diff --git a/coderd/oauth2provider/metadata_test.go b/coderd/oauth2provider/metadata_test.go
index 6ce480e335..db3152f5c0 100644
--- a/coderd/oauth2provider/metadata_test.go
+++ b/coderd/oauth2provider/metadata_test.go
@@ -119,6 +119,31 @@ func TestGetAuthorizationServerMetadata_DCREnabled(t *testing.T) {
 	}
 }
 
+func TestOAuth2ProtectedResourceMetadataUnknownPath(t *testing.T) {
+	t.Parallel()
+
+	client := coderdtest.New(t, nil)
+	for _, suffix := range []string{
+		"/unknown", "/api/v2/users/me", "/api/experimental/mcp/http/unknown",
+		"/api/experimental/mcp/http-extra", "/../api/experimental/mcp/http",
+		"/api/experimental/mcp/../mcp/http", "/api//experimental/mcp/http",
+		"//api/experimental/mcp/http", "/api/experimental/mcp/http//",
+		"/api/experimental/mcp/%2e%2e/mcp/http", "/%ff",
+	} {
+		t.Run(suffix, func(t *testing.T) {
+			t.Parallel()
+			ctx := testutil.Context(t, testutil.WaitLong)
+			req, err := http.NewRequestWithContext(ctx, http.MethodGet,
+				client.URL.String()+"/.well-known/oauth-protected-resource"+suffix, nil)
+			require.NoError(t, err)
+			resp, err := client.HTTPClient.Do(req)
+			require.NoError(t, err)
+			defer resp.Body.Close()
+			require.Equal(t, http.StatusNotFound, resp.StatusCode)
+		})
+	}
+}
+
 func TestOAuth2ProtectedResourceMetadata(t *testing.T) {
 	t.Parallel()
 
@@ -135,10 +160,17 @@ func TestOAuth2ProtectedResourceMetadata(t *testing.T) {
 	testutil.RequireEventuallyResponseOK(ctx, t, endpoint, &metadata)
 
 	// Verify the metadata
-	require.NotEmpty(t, metadata.Resource)
+	require.Equal(t, serverURL.String(), metadata.Resource)
 	require.NotEmpty(t, metadata.AuthorizationServers)
 	require.Len(t, metadata.AuthorizationServers, 1)
 	require.Equal(t, metadata.Resource, metadata.AuthorizationServers[0])
+
+	for _, suffix := range []string{"/api/experimental/mcp/http", "/api/experimental/mcp/http/"} {
+		var pathMetadata codersdk.OAuth2ProtectedResourceMetadata
+		testutil.RequireEventuallyResponseOK(ctx, t, endpoint+suffix, &pathMetadata)
+		require.Equal(t, serverURL.String()+suffix, pathMetadata.Resource)
+		require.Equal(t, []string{serverURL.String()}, pathMetadata.AuthorizationServers)
+	}
 	// RFC 6750 bearer tokens are now supported as fallback methods
 	require.Contains(t, metadata.BearerMethodsSupported, "header")
 	require.Contains(t, metadata.BearerMethodsSupported, "query")
diff --git a/coderd/oauth2provider/ratelimit_test.go b/coderd/oauth2provider/ratelimit_test.go
index 17b17388b4..0db3499595 100644
--- a/coderd/oauth2provider/ratelimit_test.go
+++ b/coderd/oauth2provider/ratelimit_test.go
@@ -168,7 +168,7 @@ func TestOAuth2RateLimit(t *testing.T) {
 		requireLimited(t, func() *http.Response {
 			uri := baseURL + "/.well-known/oauth-protected-resource/" + uuid.NewString()
 			return doRequest(ctx, t, http.MethodGet, uri, nil)
-		}, http.StatusOK)
+		}, http.StatusNotFound)
 	})
 
 	t.Run("SeparateBucketPerEndpoint", func(t *testing.T) {
diff --git a/codersdk/mcp.go b/codersdk/mcp.go
index 9d222dfa1e..af3881cf6d 100644
--- a/codersdk/mcp.go
+++ b/codersdk/mcp.go
@@ -9,6 +9,9 @@ import (
 	"github.com/google/uuid"
 )
 
+// MCPEndpoint is the remote MCP HTTP endpoint path.
+const MCPEndpoint = "/api/experimental/mcp/http"
+
 // MCPServerOAuth2ConnectURL returns the URL the user should visit to
 // start the OAuth2 flow for an MCP server. The frontend opens this
 // in a new window/popup.
diff --git a/codersdk/organizations.go b/codersdk/organizations.go
index bb64af5ec9..e5edd794e3 100644
--- a/codersdk/organizations.go
+++ b/codersdk/organizations.go
@@ -674,6 +674,10 @@ func (c *Client) CreateWorkspace(ctx context.Context, _ uuid.UUID, user string,
 
 // CreateUserWorkspace creates a new workspace for the template specified.
 func (c *Client) CreateUserWorkspace(ctx context.Context, user string, request CreateWorkspaceRequest) (Workspace, error) {
+	// Validate before URL resolution can interpret user input as a path or query.
+	if err := validateWorkspacePathSegment(user); err != nil {
+		return Workspace{}, xerrors.Errorf("invalid user: %w", err)
+	}
 	res, err := c.Request(ctx, http.MethodPost, fmt.Sprintf("/api/v2/users/%s/workspaces", user), request)
 	if err != nil {
 		return Workspace{}, err
diff --git a/codersdk/toolsdk/toolsdk_test.go b/codersdk/toolsdk/toolsdk_test.go
index f9e29c56d2..64d383f44a 100644
--- a/codersdk/toolsdk/toolsdk_test.go
+++ b/codersdk/toolsdk/toolsdk_test.go
@@ -1135,15 +1135,23 @@ func TestTools(t *testing.T) {
 		tb, err := toolsdk.NewDeps(client)
 		require.NoError(t, err)
 		t.Run("WithoutPreset", func(t *testing.T) {
-			res, err := testTool(t, toolsdk.CreateWorkspace, tb, toolsdk.CreateWorkspaceArgs{
-				User:              "me",
-				TemplateVersionID: r.TemplateVersion.ID.String(),
-				Name:              testutil.GetRandomNameHyphenated(t),
-				RichParameters:    map[string]string{},
-			})
-
-			require.NoError(t, err)
-			require.NotEmpty(t, res.ID, "expected a workspace ID")
+			for _, user := range []string{"", codersdk.Me, member.Username, member.ID.String()} {
+				t.Run(user, func(t *testing.T) {
+					res, err := testTool(t, toolsdk.CreateWorkspace, tb, toolsdk.CreateWorkspaceArgs{
+						User:              user,
+						TemplateVersionID: r.TemplateVersion.ID.String(),
+						Name:              testutil.GetRandomNameHyphenated(t),
+						RichParameters:    map[string]string{},
+					})
+					require.NoError(t, err)
+					require.NotEqual(t, uuid.Nil, res.ID)
+					if user == member.Username || user == member.ID.String() {
+						require.Equal(t, member.ID, res.OwnerID)
+					} else {
+						require.Equal(t, owner.UserID, res.OwnerID)
+					}
+				})
+			}
 		})
 
 		t.Run("WithPreset", func(t *testing.T) {
diff --git a/codersdk/workspaces.go b/codersdk/workspaces.go
index d928579b39..18fe0b8286 100644
--- a/codersdk/workspaces.go
+++ b/codersdk/workspaces.go
@@ -651,6 +651,13 @@ func (c *Client) Workspaces(ctx context.Context, filter WorkspaceFilter) (Worksp
 
 // WorkspaceByOwnerAndName returns a workspace by the owner's UUID and the workspace's name.
 func (c *Client) WorkspaceByOwnerAndName(ctx context.Context, owner string, name string, params WorkspaceOptions) (Workspace, error) {
+	// These identifiers must remain individual path segments during URL resolution.
+	if err := validateWorkspacePathSegment(owner); err != nil {
+		return Workspace{}, xerrors.Errorf("invalid workspace owner: %w", err)
+	}
+	if err := validateWorkspacePathSegment(name); err != nil {
+		return Workspace{}, xerrors.Errorf("invalid workspace name: %w", err)
+	}
 	res, err := c.Request(ctx, http.MethodGet, fmt.Sprintf("/api/v2/users/%s/workspace/%s", owner, name), nil, func(r *http.Request) {
 		q := r.URL.Query()
 		q.Set("include_deleted", fmt.Sprintf("%t", params.IncludeDeleted))
@@ -669,6 +676,15 @@ func (c *Client) WorkspaceByOwnerAndName(ctx context.Context, owner string, name
 	return workspace, ReadBodyAsJSON(res, &workspace)
 }
 
+// validateWorkspacePathSegment prevents workspace and user identifiers from
+// changing the endpoint during URL resolution, without restricting legacy names.
+func validateWorkspacePathSegment(identifier string) error {
+	if identifier == "" || identifier == "." || identifier == ".." || strings.ContainsAny(identifier, `/\%?#`) {
+		return xerrors.New("must be a non-empty path segment without slashes, escapes, query, fragment, or dot segments")
+	}
+	return nil
+}
+
 // SplitWorkspaceIdentifier splits an identifier into owner and
 // workspace name. A bare name defaults the owner to Me ("me"). An
 // "owner/name" pair is accepted, and identifiers with more than one
diff --git a/codersdk/workspaces_test.go b/codersdk/workspaces_test.go
index 63cb99e062..6b62e76b4c 100644
--- a/codersdk/workspaces_test.go
+++ b/codersdk/workspaces_test.go
@@ -19,6 +19,53 @@ import (
 	"github.com/coder/coder/v2/testutil"
 )
 
+func TestWorkspacePathSegments(t *testing.T) {
+	t.Parallel()
+
+	for _, identifier := range []string{
+		codersdk.Me, "alice", "legacy_name", uuid.NewString(),
+		"me/keys/tokens?", "me/keys/tokens#", "../users/me", "me%2fkeys",
+		"me%252fkeys", `me\keys`, "", ".", "..",
+	} {
+		t.Run(identifier, func(t *testing.T) {
+			t.Parallel()
+			valid := identifier == codersdk.Me || identifier == "alice" || identifier == "legacy_name"
+			if _, err := uuid.Parse(identifier); err == nil {
+				valid = true
+			}
+			origin, err := url.Parse("https://coder.example.com")
+			require.NoError(t, err)
+			var calls int
+			client := codersdk.New(origin, codersdk.WithHTTPClient(&http.Client{
+				Transport: testutil.RoundTripperFunc(func(req *http.Request) (*http.Response, error) {
+					calls++
+					assert.Equal(t, origin.Host, req.URL.Host)
+					assert.Empty(t, req.URL.Fragment)
+					if req.Method == http.MethodPost {
+						assert.Equal(t, "/api/v2/users/"+identifier+"/workspaces", req.URL.Path)
+						assert.Empty(t, req.URL.RawQuery)
+					} else {
+						assert.Equal(t, "/api/v2/users/"+identifier+"/workspace/legacy_name", req.URL.Path)
+						assert.Equal(t, "include_deleted=false", req.URL.RawQuery)
+					}
+					return nil, xerrors.New("request reached transport")
+				}),
+			}))
+			_, createErr := client.CreateUserWorkspace(t.Context(), identifier, codersdk.CreateWorkspaceRequest{})
+			_, lookupErr := client.WorkspaceByOwnerAndName(t.Context(), identifier, "legacy_name", codersdk.WorkspaceOptions{})
+			if valid {
+				require.ErrorContains(t, createErr, "request reached transport")
+				require.ErrorContains(t, lookupErr, "request reached transport")
+				require.Equal(t, 2, calls)
+			} else {
+				require.ErrorContains(t, createErr, "invalid user")
+				require.ErrorContains(t, lookupErr, "invalid workspace owner")
+				require.Zero(t, calls)
+			}
+		})
+	}
+}
+
 func TestResolveWorkspace(t *testing.T) {
 	t.Parallel()
 
@@ -293,20 +340,26 @@ func TestResolveWorkspace(t *testing.T) {
 	t.Run("InvalidIdentifier", func(t *testing.T) {
 		t.Parallel()
 
-		var hits atomic.Int64
-		srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, req *http.Request) {
-			hits.Add(1)
-			t.Errorf("unexpected HTTP request for invalid identifier: %s", req.URL.Path)
-		}))
-		defer srv.Close()
-
-		u, err := url.Parse(srv.URL)
-		require.NoError(t, err)
-		client := codersdk.New(u)
-
-		_, err = client.ResolveWorkspace(t.Context(), "a/b/c")
-		require.Error(t, err)
-		require.ErrorContains(t, err, "invalid workspace identifier: \"a/b/c\"")
-		require.EqualValues(t, 0, hits.Load(), "invalid identifiers should fail before any HTTP request")
+		for _, identifier := range []string{
+			"a/b/c", "me?/workspace", "me#/workspace", "me%3f/workspace",
+			"../workspace", "./workspace", "workspace?after=1", "workspace#fragment",
+			"%2e%2e", "me%252fkeys/workspace", `me\keys/workspace`, "..", ".", "", "/workspace", "me/",
+		} {
+			t.Run(identifier, func(t *testing.T) {
+				t.Parallel()
+				var hits atomic.Int64
+				srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, req *http.Request) {
+					hits.Add(1)
+					t.Errorf("unexpected HTTP request for invalid identifier: %s", req.URL.Path)
+				}))
+				t.Cleanup(srv.Close)
+				u, err := url.Parse(srv.URL)
+				require.NoError(t, err)
+				client := codersdk.New(u)
+				_, err = client.ResolveWorkspace(t.Context(), identifier)
+				require.ErrorContains(t, err, "invalid workspace")
+				require.EqualValues(t, 0, hits.Load(), "invalid identifiers should fail before any HTTP request")
+			})
+		}
 	})
 }
diff --git a/docs/admin/integrations/oauth2-provider/integration-patterns.md b/docs/admin/integrations/oauth2-provider/integration-patterns.md
index fe303f2e44..e97a48cfc3 100644
--- a/docs/admin/integrations/oauth2-provider/integration-patterns.md
+++ b/docs/admin/integrations/oauth2-provider/integration-patterns.md
@@ -121,9 +121,13 @@ Coder enforces PKCE in compliance with the OAuth 2.1 specification, for both pub
 Coder provides OAuth2 discovery endpoints for programmatic integration:
 
 - **Authorization Server Metadata**: `GET /.well-known/oauth-authorization-server`
-- **Protected Resource Metadata**: `GET /.well-known/oauth-protected-resource`
+- **REST API protected resource metadata**: `GET /.well-known/oauth-protected-resource`
+- **MCP protected resource metadata**: `GET /.well-known/oauth-protected-resource/api/experimental/mcp/http`
 
 These endpoints return server capabilities and endpoint URLs according to [RFC 8414](https://datatracker.ietf.org/doc/html/rfc8414) and [RFC 9728](https://datatracker.ietf.org/doc/html/rfc9728).
+The REST API metadata identifies the deployment URL as its `resource`, while the MCP metadata identifies the full MCP endpoint URL.
+Both list the deployment URL in `authorization_servers` and use the same authorization server metadata endpoint.
+OAuth2 tokens issued for the MCP resource work with MCP tools.
 
 `token_endpoint_auth_methods_supported` lists every method the token endpoint accepts, including `none`.
 It is not gated on [Dynamic Client Registration](./index.md#dynamic-client-registration), since existing public clients still exchange tokens when new registrations are disabled.
diff --git a/docs/ai-coder/mcp-server.md b/docs/ai-coder/mcp-server.md
index 353038575e..c5704ed6cc 100644
--- a/docs/ai-coder/mcp-server.md
+++ b/docs/ai-coder/mcp-server.md
@@ -178,15 +178,16 @@ The MCP server supports two authentication methods:
 
 ### OAuth2 (Recommended for Interactive Clients)
 
-MCP clients that support [RFC 9728](https://datatracker.ietf.org/doc/html/rfc9728)
-(Protected Resource Metadata) can authenticate automatically using OAuth2. The
-server advertises its OAuth2 capabilities via the `WWW-Authenticate` header and
-`/.well-known/oauth-protected-resource` endpoint.
-
+MCP clients that support [RFC 9728](https://datatracker.ietf.org/doc/html/rfc9728) (Protected Resource Metadata) can authenticate automatically using OAuth2.
 This enables a seamless connect-and-authenticate experience where users sign in through their browser without manually managing tokens.
 
+The MCP endpoint's `WWW-Authenticate` header points to `/.well-known/oauth-protected-resource/api/experimental/mcp/http` through its `resource_metadata` parameter.
+This metadata identifies the full MCP endpoint URL as the `resource`, for example, `https://coder.example.com/api/experimental/mcp/http`.
+
 > [!NOTE]
 > OAuth2 requires `CODER_OAUTH2_PROVIDER_ENABLE=true` on your Coder deployment.
+>
+> [Dynamic Client Registration (DCR)](../admin/integrations/oauth2-provider/index.md#dynamic-client-registration) is off by default and must be enabled before clients can self-register.
 
 ### Session Token (For Programmatic Access)
 
@@ -252,5 +253,6 @@ them for you to invoke, for example as slash commands:
 ### OAuth2 authentication not working
 
 - Ensure your Coder deployment has `CODER_OAUTH2_PROVIDER_ENABLE=true` set
+- If your client registers itself automatically, ensure [Dynamic Client Registration](../admin/integrations/oauth2-provider/index.md#dynamic-client-registration) is enabled
 - Verify your MCP client supports RFC 9728 Protected Resource Metadata
 - Check that your browser can reach the Coder authorization endpoint
diff --git a/site/src/api/typesGenerated.ts b/site/src/api/typesGenerated.ts
index 64761a1527..521e720f5e 100644
--- a/site/src/api/typesGenerated.ts
+++ b/site/src/api/typesGenerated.ts
@@ -6701,6 +6701,12 @@ export interface LoginWithPasswordResponse {
 	readonly session_token: string;
 }
 
+// From codersdk/mcp.go
+/**
+ * MCPEndpoint is the remote MCP HTTP endpoint path.
+ */
+export const MCPEndpoint = "/api/experimental/mcp/http";
+
 // From codersdk/mcp.go
 /**
  * MCPServerConfig represents an admin-configured MCP server.