diff --git a/src/main/services/mcpOAuthService.ts b/src/main/services/mcpOAuthService.ts
index 50957c7..bb66a6b 100644
--- a/src/main/services/mcpOAuthService.ts
+++ b/src/main/services/mcpOAuthService.ts
@@ -5,7 +5,7 @@ import electron from 'electron';
 
 import type { McpOauthStaticClientConfig } from '@shared/domain/mcpAuth';
 
-import { storeToken, buildWellKnownUrl, buildWellKnownUrlFallback, type McpOAuthToken } from './mcpTokenStore';
+import { storeToken, buildWellKnownUrl, buildWellKnownUrlFallback, buildWellKnownUrlOriginOnly, type McpOAuthToken } from './mcpTokenStore';
 
 const { shell } = electron;
 
@@ -228,7 +228,18 @@ interface AuthServerMetadata {
 async function fetchWellKnownMetadata(baseUrl: string, suffix: string): Promise<Record<string, unknown> | undefined> {
   const rfcUrl = buildWellKnownUrl(baseUrl, suffix);
   const fallbackUrl = buildWellKnownUrlFallback(baseUrl, suffix);
-  const urls = rfcUrl === fallbackUrl ? [rfcUrl] : [rfcUrl, fallbackUrl];
+  const originOnlyUrl = buildWellKnownUrlOriginOnly(baseUrl, suffix);
+
+  // Deduplicate: RFC path, appended fallback, then origin-only (for servers
+  // that serve metadata at the origin without the resource path suffix).
+  const seen = new Set<string>();
+  const urls: string[] = [];
+  for (const url of [rfcUrl, fallbackUrl, originOnlyUrl]) {
+    if (!seen.has(url)) {
+      seen.add(url);
+      urls.push(url);
+    }
+  }
 
   for (const url of urls) {
     try {
diff --git a/src/main/services/mcpTokenStore.ts b/src/main/services/mcpTokenStore.ts
index e92a1ae..dedaa70 100644
--- a/src/main/services/mcpTokenStore.ts
+++ b/src/main/services/mcpTokenStore.ts
@@ -66,3 +66,8 @@ export function buildWellKnownUrlFallback(baseUrl: string, wellKnownSuffix: stri
   const base = baseUrl.replace(/\/+$/, '');
   return `${base}/.well-known/${wellKnownSuffix}`;
 }
+
+export function buildWellKnownUrlOriginOnly(baseUrl: string, wellKnownSuffix: string): string {
+  const parsed = new URL(baseUrl);
+  return `${parsed.origin}/.well-known/${wellKnownSuffix}`;
+}
diff --git a/tests/main/mcpOAuthDiscovery.test.ts b/tests/main/mcpOAuthDiscovery.test.ts
index 4a8f55d..83f5464 100644
--- a/tests/main/mcpOAuthDiscovery.test.ts
+++ b/tests/main/mcpOAuthDiscovery.test.ts
@@ -1,6 +1,6 @@
 import { describe, expect, test } from 'bun:test';
 
-import { buildWellKnownUrl, buildWellKnownUrlFallback } from '@main/services/mcpTokenStore';
+import { buildWellKnownUrl, buildWellKnownUrlFallback, buildWellKnownUrlOriginOnly } from '@main/services/mcpTokenStore';
 
 describe('buildWellKnownUrl', () => {
   test('inserts well-known segment after origin for URL with path', () => {
@@ -50,3 +50,25 @@ describe('buildWellKnownUrlFallback', () => {
       .toBe('https://auth.example.com/.well-known/oauth-authorization-server');
   });
 });
+
+describe('buildWellKnownUrlOriginOnly', () => {
+  test('strips path and returns origin-only well-known URL', () => {
+    expect(buildWellKnownUrlOriginOnly('https://eschat.microsoft.com/mcp', 'oauth-protected-resource'))
+      .toBe('https://eschat.microsoft.com/.well-known/oauth-protected-resource');
+  });
+
+  test('handles multi-level path', () => {
+    expect(buildWellKnownUrlOriginOnly('https://example.com/v1/mcp/api', 'oauth-protected-resource'))
+      .toBe('https://example.com/.well-known/oauth-protected-resource');
+  });
+
+  test('matches RFC URL when base has no path', () => {
+    expect(buildWellKnownUrlOriginOnly('https://auth.example.com/', 'oauth-authorization-server'))
+      .toBe('https://auth.example.com/.well-known/oauth-authorization-server');
+  });
+
+  test('handles URL with port', () => {
+    expect(buildWellKnownUrlOriginOnly('https://mcp.example.com:8443/v1/', 'oauth-protected-resource'))
+      .toBe('https://mcp.example.com:8443/.well-known/oauth-protected-resource');
+  });
+});