From 7c38d6d1b042b149a003e9291d1b83900be05f8f Mon Sep 17 00:00:00 2001
From: Dustin Healy <54083382+dustinhealy@users.noreply.github.com>
Date: Tue, 9 Dec 2025 07:01:37 -0800
Subject: [PATCH] fix: attempt reconnection on token expiry

---
 .../oauth/OAuthReconnectionManager.test.ts    | 35 ++++++++++++++++---
 .../src/mcp/oauth/OAuthReconnectionManager.ts |  6 ----
 2 files changed, 31 insertions(+), 10 deletions(-)

diff --git a/packages/api/src/mcp/oauth/OAuthReconnectionManager.test.ts b/packages/api/src/mcp/oauth/OAuthReconnectionManager.test.ts
index f9a3c7ab73..f8f17bd54c 100644
--- a/packages/api/src/mcp/oauth/OAuthReconnectionManager.test.ts
+++ b/packages/api/src/mcp/oauth/OAuthReconnectionManager.test.ts
@@ -250,23 +250,50 @@ describe('OAuthReconnectionManager', () => {
       expect(mockMCPManager.disconnectUserConnection).toHaveBeenCalledWith(userId, 'server1');
     });
 
-    it('should not reconnect servers with expired tokens', async () => {
+    it('should attempt to reconnect servers with expired tokens (refresh will be attempted)', async () => {
       const userId = 'user-123';
       const oauthServers = new Set(['server1']);
       (mcpServersRegistry.getOAuthServers as jest.Mock).mockResolvedValue(oauthServers);
 
-      // server1: has expired token
+      // server1: has expired token (but refresh token should still work)
       tokenMethods.findToken.mockResolvedValue({
         userId,
         identifier: 'mcp:server1',
         expiresAt: new Date(Date.now() - 3600000), // 1 hour ago
       } as unknown as MCPOAuthTokens);
 
+      // Mock successful reconnection (token refresh happens internally)
+      const mockConnection = {
+        isConnected: jest.fn().mockResolvedValue(true),
+      };
+      mockMCPManager.getUserConnection.mockResolvedValue(
+        mockConnection as unknown as MCPConnection,
+      );
+      (mcpServersRegistry.getServerConfig as jest.Mock).mockResolvedValue(
+        {} as unknown as MCPOptions,
+      );
+
       await reconnectionManager.reconnectServers(userId);
 
-      // Verify no reconnection attempt was made
+      // Verify reconnection attempt was made (token refresh will happen during getUserConnection)
+      expect(reconnectionTracker.isActive(userId, 'server1')).toBe(true);
+
+      // Wait for async tryReconnect to complete
+      await new Promise((resolve) => setTimeout(resolve, 100));
+
+      expect(mockMCPManager.getUserConnection).toHaveBeenCalledWith({
+        serverName: 'server1',
+        user: { id: userId },
+        flowManager,
+        tokenMethods,
+        forceNew: false,
+        connectionTimeout: 10000, // DEFAULT_CONNECTION_TIMEOUT_MS
+        returnOnOAuth: true,
+      });
+
+      // Verify successful reconnection cleared the states
+      expect(reconnectionTracker.isFailed(userId, 'server1')).toBe(false);
       expect(reconnectionTracker.isActive(userId, 'server1')).toBe(false);
-      expect(mockMCPManager.getUserConnection).not.toHaveBeenCalled();
     });
 
     it('should handle connection that returns but is not connected', async () => {
diff --git a/packages/api/src/mcp/oauth/OAuthReconnectionManager.ts b/packages/api/src/mcp/oauth/OAuthReconnectionManager.ts
index db81a2ffae..3130e9cc43 100644
--- a/packages/api/src/mcp/oauth/OAuthReconnectionManager.ts
+++ b/packages/api/src/mcp/oauth/OAuthReconnectionManager.ts
@@ -174,12 +174,6 @@ export class OAuthReconnectionManager {
       return false;
     }
 
-    // if the token has expired, don't attempt to reconnect
-    const now = new Date();
-    if (accessToken.expiresAt && accessToken.expiresAt < now) {
-      return false;
-    }
-
     // …otherwise, we're good to go with the reconnect attempt
     return true;
   }