diff --git a/apps/web/src/lib/connectors/__tests__/oauth-metadata.test.ts b/apps/web/src/lib/connectors/__tests__/oauth-metadata.test.ts
index d68f99e5..ecfeea67 100644
--- a/apps/web/src/lib/connectors/__tests__/oauth-metadata.test.ts
+++ b/apps/web/src/lib/connectors/__tests__/oauth-metadata.test.ts
@@ -93,6 +93,31 @@ describe('oauth-metadata', () => {
         tokenEndpoint: 'https://example.com/token',
         registrationEndpoint: 'https://example.com/register',
       })
+      // RFC 8414: server URLs with a path component are discovered through the
+      // path-aware well-known document first.
+      expect(mockFetch).toHaveBeenCalledTimes(1)
+      expect(mockFetch).toHaveBeenCalledWith('https://example.com/.well-known/oauth-authorization-server/mcp', {
+        method: 'GET',
+        headers: { Accept: 'application/json' },
+        cache: 'no-store',
+      })
+
+      vi.unstubAllGlobals()
+    })
+
+    it('queries the root well-known document directly when the server URL has no path', async () => {
+      const mockFetch = vi.fn().mockResolvedValue({
+        ok: true,
+        json: async () => ({
+          authorization_endpoint: 'https://example.com/auth',
+          token_endpoint: 'https://example.com/token',
+        }),
+      })
+      vi.stubGlobal('fetch', mockFetch)
+
+      const { discoverOAuthMetadata } = await import('@/lib/connectors/oauth-metadata')
+      await discoverOAuthMetadata('https://example.com/')
+      expect(mockFetch).toHaveBeenCalledTimes(1)
       expect(mockFetch).toHaveBeenCalledWith('https://example.com/.well-known/oauth-authorization-server', {
         method: 'GET',
         headers: { Accept: 'application/json' },
@@ -102,6 +127,57 @@ describe('oauth-metadata', () => {
       vi.unstubAllGlobals()
     })
 
+    it('falls back to the root well-known document when the path-aware document is missing', async () => {
+      const mockFetch = vi.fn()
+        .mockResolvedValueOnce({ ok: false, status: 404 })
+        .mockResolvedValueOnce({
+          ok: true,
+          json: async () => ({
+            issuer: 'https://example.com',
+            authorization_endpoint: 'https://example.com/auth',
+            token_endpoint: 'https://example.com/token',
+          }),
+        })
+      vi.stubGlobal('fetch', mockFetch)
+
+      const { discoverOAuthMetadata } = await import('@/lib/connectors/oauth-metadata')
+      const result = await discoverOAuthMetadata('https://example.com/mcp')
+      expect(result.authorizationEndpoint).toBe('https://example.com/auth')
+      expect(mockFetch).toHaveBeenNthCalledWith(1, 'https://example.com/.well-known/oauth-authorization-server/mcp', expect.any(Object))
+      expect(mockFetch).toHaveBeenNthCalledWith(2, 'https://example.com/.well-known/oauth-authorization-server', expect.any(Object))
+
+      vi.unstubAllGlobals()
+    })
+
+    it('uses path-aware metadata for servers hosted under a path (Meta Ads MCP shape)', async () => {
+      const mockFetch = vi.fn(async (url: string) => {
+        if (url === 'https://mcp.facebook.com/.well-known/oauth-authorization-server/ads') {
+          return {
+            ok: true,
+            json: async () => ({
+              issuer: 'https://www.facebook.com',
+              authorization_endpoint: 'https://www.facebook.com/v26.0/dialog/oauth',
+              token_endpoint: 'https://graph.facebook.com/v26.0/oauth/access_token',
+              registration_endpoint: 'https://mcp.facebook.com/.well-known/register/ads',
+            }),
+          }
+        }
+        return { ok: false, status: 404 }
+      })
+      vi.stubGlobal('fetch', mockFetch)
+
+      const { discoverOAuthMetadata } = await import('@/lib/connectors/oauth-metadata')
+      const result = await discoverOAuthMetadata('https://mcp.facebook.com/ads')
+      expect(result).toEqual({
+        issuer: 'https://www.facebook.com',
+        authorizationEndpoint: 'https://www.facebook.com/v26.0/dialog/oauth',
+        tokenEndpoint: 'https://graph.facebook.com/v26.0/oauth/access_token',
+        registrationEndpoint: 'https://mcp.facebook.com/.well-known/register/ads',
+      })
+
+      vi.unstubAllGlobals()
+    })
+
     it('throws when metadata response is missing required fields', async () => {
       const mockFetch = vi.fn().mockResolvedValue({
         ok: true,
diff --git a/apps/web/src/lib/connectors/oauth-metadata.ts b/apps/web/src/lib/connectors/oauth-metadata.ts
index 8ac92d1a..e1334cd6 100644
--- a/apps/web/src/lib/connectors/oauth-metadata.ts
+++ b/apps/web/src/lib/connectors/oauth-metadata.ts
@@ -30,37 +30,59 @@ export async function sanitizeOAuthMetadata(metadata: OAuthServerMetadata): Prom
   }
 }
 
+function buildWellKnownMetadataUrls(serverUrl: URL): string[] {
+  const authorizationBase = `${serverUrl.protocol}//${serverUrl.host}`
+  const rootMetadataUrl = `${authorizationBase}/.well-known/oauth-authorization-server`
+  const serverPath = serverUrl.pathname.replace(/\/+$/, '')
+
+  // RFC 8414 §3.1: when the issuer has a path component, the well-known suffix
+  // is inserted between the host and the path (e.g. https://mcp.facebook.com/ads
+  // publishes metadata at /.well-known/oauth-authorization-server/ads).
+  // The root document is kept as a fallback for servers that only publish there.
+  if (serverPath) {
+    return [`${rootMetadataUrl}${serverPath}`, rootMetadataUrl]
+  }
+
+  return [rootMetadataUrl]
+}
+
 export async function discoverOAuthMetadata(mcpServerUrl: string): Promise<OAuthServerMetadata> {
   const serverUrl = new URL(mcpServerUrl)
   const authorizationBase = `${serverUrl.protocol}//${serverUrl.host}`
-  const metadataUrl = `${authorizationBase}/.well-known/oauth-authorization-server`
+  const metadataUrls = buildWellKnownMetadataUrls(serverUrl)
 
-  const metadataResponse = await fetch(metadataUrl, {
-    method: 'GET',
-    headers: {
-      Accept: 'application/json',
-    },
-    cache: 'no-store',
-  }).catch(() => null)
+  for (const [index, metadataUrl] of metadataUrls.entries()) {
+    const isLastCandidate = index === metadataUrls.length - 1
 
-  if (metadataResponse && metadataResponse.ok) {
-    const data = (await metadataResponse.json().catch(() => null)) as Record<string, unknown> | null
-    const authorizationEndpoint = getString(data?.authorization_endpoint)
-    const tokenEndpoint = getString(data?.token_endpoint)
-    if (!authorizationEndpoint || !tokenEndpoint) {
-      throw new Error('oauth_discovery_failed:invalid_metadata')
-    }
+    const metadataResponse = await fetch(metadataUrl, {
+      method: 'GET',
+      headers: {
+        Accept: 'application/json',
+      },
+      cache: 'no-store',
+    }).catch(() => null)
+
+    if (metadataResponse && metadataResponse.ok) {
+      const data = (await metadataResponse.json().catch(() => null)) as Record<string, unknown> | null
+      const authorizationEndpoint = getString(data?.authorization_endpoint)
+      const tokenEndpoint = getString(data?.token_endpoint)
+      if (!authorizationEndpoint || !tokenEndpoint) {
+        throw new Error('oauth_discovery_failed:invalid_metadata')
+      }
 
-    return {
-      issuer: getString(data?.issuer),
-      authorizationEndpoint,
-      tokenEndpoint,
-      registrationEndpoint: getString(data?.registration_endpoint),
+      return {
+        issuer: getString(data?.issuer),
+        authorizationEndpoint,
+        tokenEndpoint,
+        registrationEndpoint: getString(data?.registration_endpoint),
+      }
     }
-  }
 
-  if (metadataResponse && metadataResponse.status !== 404) {
-    throw new Error(`oauth_discovery_failed:${metadataResponse.status}`)
+    // Non-404 errors on intermediate candidates fall through to the next
+    // candidate; only the final (root) document keeps strict error semantics.
+    if (isLastCandidate && metadataResponse && metadataResponse.status !== 404) {
+      throw new Error(`oauth_discovery_failed:${metadataResponse.status}`)
+    }
   }
 
   return {