diff --git a/src/features/mcp-oauth/discovery.test.ts b/src/features/mcp-oauth/discovery.test.ts
index 8fbced17f..5253b200e 100644
--- a/src/features/mcp-oauth/discovery.test.ts
+++ b/src/features/mcp-oauth/discovery.test.ts
@@ -90,6 +90,69 @@ describe("discoverOAuthServerMetadata", () => {
     })
   })
 
+  test("falls back to root well-known URL when resource has a sub-path", () => {
+    // given — resource URL has a /mcp path (e.g. https://mcp.sentry.dev/mcp)
+    const resource = "https://mcp.example.com/mcp"
+    const prmUrl = new URL("/.well-known/oauth-protected-resource", resource).toString()
+    const pathSuffixedAsUrl = "https://mcp.example.com/.well-known/oauth-authorization-server/mcp"
+    const rootAsUrl = "https://mcp.example.com/.well-known/oauth-authorization-server"
+    const calls: string[] = []
+    const fetchMock = async (input: string | URL) => {
+      const url = typeof input === "string" ? input : input.toString()
+      calls.push(url)
+      if (url === prmUrl) {
+        return new Response("not found", { status: 404 })
+      }
+      if (url === pathSuffixedAsUrl) {
+        return new Response("not found", { status: 404 })
+      }
+      if (url === rootAsUrl) {
+        return new Response(
+          JSON.stringify({
+            authorization_endpoint: "https://mcp.example.com/oauth/authorize",
+            token_endpoint: "https://mcp.example.com/oauth/token",
+            registration_endpoint: "https://mcp.example.com/oauth/register",
+          }),
+          { status: 200 }
+        )
+      }
+      return new Response("not found", { status: 404 })
+    }
+    Object.defineProperty(globalThis, "fetch", { value: fetchMock, configurable: true })
+
+    // when
+    return discoverOAuthServerMetadata(resource).then((result) => {
+      // then
+      expect(result).toEqual({
+        authorizationEndpoint: "https://mcp.example.com/oauth/authorize",
+        tokenEndpoint: "https://mcp.example.com/oauth/token",
+        registrationEndpoint: "https://mcp.example.com/oauth/register",
+        resource,
+      })
+      expect(calls).toEqual([prmUrl, pathSuffixedAsUrl, rootAsUrl])
+    })
+  })
+
+  test("throws when PRM, path-suffixed AS, and root AS all return 404", () => {
+    // given
+    const resource = "https://mcp.example.com/mcp"
+    const prmUrl = new URL("/.well-known/oauth-protected-resource", resource).toString()
+    const fetchMock = async (input: string | URL) => {
+      const url = typeof input === "string" ? input : input.toString()
+      if (url === prmUrl || url.includes(".well-known/oauth-authorization-server")) {
+        return new Response("not found", { status: 404 })
+      }
+      return new Response("not found", { status: 404 })
+    }
+    Object.defineProperty(globalThis, "fetch", { value: fetchMock, configurable: true })
+
+    // when
+    const result = discoverOAuthServerMetadata(resource)
+
+    // then
+    return expect(result).rejects.toThrow("OAuth authorization server metadata not found")
+  })
+
   test("throws when both PRM and AS discovery return 404", () => {
     // given
     const resource = "https://mcp.example.com"
diff --git a/src/features/mcp-oauth/discovery.ts b/src/features/mcp-oauth/discovery.ts
index 619520d42..65707049b 100644
--- a/src/features/mcp-oauth/discovery.ts
+++ b/src/features/mcp-oauth/discovery.ts
@@ -36,28 +36,16 @@ async function fetchMetadata(url: string): Promise<{ ok: true; json: Record<stri
   return { ok: true, json }
 }
 
-async function fetchAuthorizationServerMetadata(issuer: string, resource: string): Promise<OAuthServerMetadata> {
-  const issuerUrl = parseHttpsUrl(issuer, "Authorization server URL")
-  const issuerPath = issuerUrl.pathname.replace(/\/+$/, "")
-  const metadataUrl = new URL(`/.well-known/oauth-authorization-server${issuerPath}`, issuerUrl).toString()
-  const metadata = await fetchMetadata(metadataUrl)
-
-  if (!metadata.ok) {
-    if (metadata.status === 404) {
-      throw new Error("OAuth authorization server metadata not found")
-    }
-    throw new Error(`OAuth authorization server metadata fetch failed (${metadata.status})`)
-  }
-
+function parseMetadataFields(json: Record<string, unknown>, resource: string): OAuthServerMetadata {
   const authorizationEndpoint = parseHttpsUrl(
-    readStringField(metadata.json, "authorization_endpoint"),
+    readStringField(json, "authorization_endpoint"),
     "authorization_endpoint"
   ).toString()
   const tokenEndpoint = parseHttpsUrl(
-    readStringField(metadata.json, "token_endpoint"),
+    readStringField(json, "token_endpoint"),
     "token_endpoint"
   ).toString()
-  const registrationEndpointValue = metadata.json.registration_endpoint
+  const registrationEndpointValue = json.registration_endpoint
   const registrationEndpoint =
     typeof registrationEndpointValue === "string" && registrationEndpointValue.length > 0
       ? parseHttpsUrl(registrationEndpointValue, "registration_endpoint").toString()
@@ -71,6 +59,29 @@ async function fetchAuthorizationServerMetadata(issuer: string, resource: string
   }
 }
 
+async function fetchAuthorizationServerMetadata(issuer: string, resource: string): Promise<OAuthServerMetadata> {
+  const issuerUrl = parseHttpsUrl(issuer, "Authorization server URL")
+  const issuerPath = issuerUrl.pathname.replace(/\/+$/, "")
+  const metadataUrl = new URL(`/.well-known/oauth-authorization-server${issuerPath}`, issuerUrl).toString()
+  const metadata = await fetchMetadata(metadataUrl)
+
+  if (!metadata.ok) {
+    if (metadata.status === 404 && issuerPath !== "") {
+      const rootMetadataUrl = new URL("/.well-known/oauth-authorization-server", issuerUrl).toString()
+      const rootMetadata = await fetchMetadata(rootMetadataUrl)
+      if (rootMetadata.ok) {
+        return parseMetadataFields(rootMetadata.json, resource)
+      }
+    }
+    if (metadata.status === 404) {
+      throw new Error("OAuth authorization server metadata not found")
+    }
+    throw new Error(`OAuth authorization server metadata fetch failed (${metadata.status})`)
+  }
+
+  return parseMetadataFields(metadata.json, resource)
+}
+
 function parseAuthorizationServers(metadata: Record<string, unknown>): string[] {
   const servers = metadata.authorization_servers
   if (!Array.isArray(servers)) return []