LibreChat/packages/api/src/mcp/connection.ts

import { EventEmitter } from 'events';
import { logger } from '@librechat/data-schemas';
import { fetch as undiciFetch, Agent } from 'undici';
import {
  StdioClientTransport,
  getDefaultEnvironment,
} from '@modelcontextprotocol/sdk/client/stdio.js';
import { Client } from '@modelcontextprotocol/sdk/client/index.js';
import { SSEClientTransport } from '@modelcontextprotocol/sdk/client/sse.js';
import { WebSocketClientTransport } from '@modelcontextprotocol/sdk/client/websocket.js';
import { ResourceListChangedNotificationSchema } from '@modelcontextprotocol/sdk/types.js';
import { StreamableHTTPClientTransport } from '@modelcontextprotocol/sdk/client/streamableHttp.js';
import type { Transport } from '@modelcontextprotocol/sdk/shared/transport.js';
import type { JSONRPCMessage } from '@modelcontextprotocol/sdk/types.js';
import type {
  RequestInit as UndiciRequestInit,
  RequestInfo as UndiciRequestInfo,
  Response as UndiciResponse,
} from 'undici';
import type { MCPOAuthTokens } from './oauth/types';
import { withTimeout } from '~/utils/promise';
import type * as t from './types';
import { createSSRFSafeUndiciConnect, resolveHostnameSSRF } from '~/auth';
import { sanitizeUrlForLogging } from './utils';
import { mcpConfig } from './mcpConfig';

type FetchLike = (url: string | URL, init?: RequestInit) => Promise<Response>;

function isStdioOptions(options: t.MCPOptions): options is t.StdioOptions {
  return 'command' in options;
}

function isWebSocketOptions(options: t.MCPOptions): options is t.WebSocketOptions {
  if ('url' in options) {
    const protocol = new URL(options.url).protocol;
    return protocol === 'ws:' || protocol === 'wss:';
  }
  return false;
}

function isSSEOptions(options: t.MCPOptions): options is t.SSEOptions {
  if ('url' in options) {
    const protocol = new URL(options.url).protocol;
    return protocol !== 'ws:' && protocol !== 'wss:';
  }
  return false;
}

/**
 * Checks if the provided options are for a Streamable HTTP transport.
 *
 * Streamable HTTP is an MCP transport that uses HTTP POST for sending messages
 * and supports streaming responses. It provides better performance than
 * SSE transport while maintaining compatibility with most network environments.
 *
 * @param options MCP connection options to check
 * @returns True if options are for a streamable HTTP transport
 */
function isStreamableHTTPOptions(options: t.MCPOptions): options is t.StreamableHTTPOptions {
  if ('url' in options && 'type' in options) {
    const optionType = options.type as string;
    if (optionType === 'streamable-http' || optionType === 'http') {
      const protocol = new URL(options.url).protocol;
      return protocol !== 'ws:' && protocol !== 'wss:';
    }
  }
  return false;
}

const FIVE_MINUTES = 5 * 60 * 1000;
const DEFAULT_TIMEOUT = 60000;
/** SSE connections through proxies may need longer initial handshake time */
const SSE_CONNECT_TIMEOUT = 120000;

/**
 * Headers for SSE connections.
 *
 * Headers we intentionally DO NOT include:
 * - Accept: text/event-stream - Already set by eventsource library AND MCP SDK
 * - X-Accel-Buffering: This is a RESPONSE header for Nginx, not a request header.
 *   The upstream MCP server must send this header for Nginx to respect it.
 * - Connection: keep-alive: Forbidden in HTTP/2 (RFC 7540 §8.1.2.2).
 *   HTTP/2 manages connection persistence differently.
 */
const SSE_REQUEST_HEADERS = {
  'Cache-Control': 'no-cache',
};

/**
 * Extracts a meaningful error message from SSE transport errors.
 * The MCP SDK's SSEClientTransport can produce "SSE error: undefined" when the
 * underlying eventsource library encounters connection issues without a specific message.
 *
 * @returns Object containing:
 *   - message: Human-readable error description
 *   - code: HTTP status code if available
 *   - isProxyHint: Whether this error suggests proxy misconfiguration
 *   - isTransient: Whether this is likely a transient error that will auto-reconnect
 */
function extractSSEErrorMessage(error: unknown): {
  message: string;
  code?: number;
  isProxyHint: boolean;
  isTransient: boolean;
} {
  if (!error || typeof error !== 'object') {
    return {
      message: 'Unknown SSE transport error',
      isProxyHint: true,
      isTransient: true,
    };
  }

  const errorObj = error as { message?: string; code?: number; event?: unknown };
  const rawMessage = errorObj.message ?? '';
  const code = errorObj.code;

  /**
   * Handle the common "SSE error: undefined" case.
   * This typically occurs when:
   * 1. A reverse proxy buffers the SSE stream (proxy issue)
   * 2. The server closes an idle connection (normal SSE behavior)
   * 3. Network interruption without specific error details
   *
   * In all cases, the eventsource library will attempt to reconnect automatically.
   */
  if (rawMessage === 'SSE error: undefined' || rawMessage === 'undefined' || !rawMessage) {
    return {
      message:
        'SSE connection closed. This can occur due to: (1) idle connection timeout (normal), ' +
        '(2) reverse proxy buffering (check proxy_buffering config), or (3) network interruption.',
      code,
      isProxyHint: true,
      isTransient: true,
    };
  }

  /**
   * Check for timeout patterns. Use case-insensitive matching for common timeout error codes:
   * - ETIMEDOUT: TCP connection timeout
   * - ESOCKETTIMEDOUT: Socket timeout
   * - "timed out" / "timeout": Generic timeout messages
   */
  const lowerMessage = rawMessage.toLowerCase();
  if (
    rawMessage.includes('ETIMEDOUT') ||
    rawMessage.includes('ESOCKETTIMEDOUT') ||
    lowerMessage.includes('timed out') ||
    lowerMessage.includes('timeout after') ||
    lowerMessage.includes('request timeout')
  ) {
    return {
      message: `SSE connection timed out: ${rawMessage}. If behind a reverse proxy, increase proxy_read_timeout.`,
      code,
      isProxyHint: true,
      isTransient: true,
    };
  }

  // Connection reset is often transient (server restart, proxy reload)
  if (rawMessage.includes('ECONNRESET')) {
    return {
      message: `SSE connection reset: ${rawMessage}. The server or proxy may have restarted.`,
      code,
      isProxyHint: false,
      isTransient: true,
    };
  }

  // Connection refused is more serious - server may be down
  if (rawMessage.includes('ECONNREFUSED')) {
    return {
      message: `SSE connection refused: ${rawMessage}. Verify the MCP server is running and accessible.`,
      code,
      isProxyHint: false,
      isTransient: false,
    };
  }

  // DNS failure is usually a configuration issue, not transient
  if (rawMessage.includes('ENOTFOUND') || rawMessage.includes('getaddrinfo')) {
    return {
      message: `SSE DNS resolution failed: ${rawMessage}. Check the server URL is correct.`,
      code,
      isProxyHint: false,
      isTransient: false,
    };
  }

  // Check for HTTP status codes in the message
  const statusMatch = rawMessage.match(/\b(4\d{2}|5\d{2})\b/);
  if (statusMatch) {
    const statusCode = parseInt(statusMatch[1], 10);
    // 5xx errors are often transient, 4xx are usually not
    const isServerError = statusCode >= 500 && statusCode < 600;
    return {
      message: rawMessage,
      code: statusCode,
      isProxyHint: statusCode === 502 || statusCode === 503 || statusCode === 504,
      isTransient: isServerError,
    };
  }

  /**
   * "fetch failed" is a generic undici TypeError that occurs when an in-flight HTTP request
   * is aborted (e.g. after an MCP protocol-level timeout fires). The transport itself is still
   * functional — only the individual request was lost — so treat this as transient.
   */
  if (rawMessage === 'fetch failed') {
    return {
      message:
        'fetch failed (request aborted, likely after a timeout — connection may still be usable)',
      code,
      isProxyHint: false,
      isTransient: true,
    };
  }

  return {
    message: rawMessage,
    code,
    isProxyHint: false,
    isTransient: false,
  };
}

interface MCPConnectionParams {
  serverName: string;
  serverConfig: t.MCPOptions;
  userId?: string;
  oauthTokens?: MCPOAuthTokens | null;
  useSSRFProtection?: boolean;
}

export class MCPConnection extends EventEmitter {
  public client: Client;
  private options: t.MCPOptions;
  private transport: Transport | null = null; // Make this nullable
  private connectionState: t.ConnectionState = 'disconnected';
  private connectPromise: Promise<void> | null = null;
  private readonly MAX_RECONNECT_ATTEMPTS = 3;
  public readonly serverName: string;
  private shouldStopReconnecting = false;
  private isReconnecting = false;
  private isInitializing = false;
  private reconnectAttempts = 0;
  private agents: Agent[] = [];
  private readonly userId?: string;
  private lastPingTime: number;
  private lastConnectionCheckAt: number = 0;
  private oauthTokens?: MCPOAuthTokens | null;
  private requestHeaders?: Record<string, string> | null;
  private oauthRequired = false;
  private readonly useSSRFProtection: boolean;
  iconPath?: string;
  timeout?: number;
  url?: string;

  /**
   * Timestamp when this connection was created.
   * Used to detect if connection is stale compared to updated config.
   */
  public readonly createdAt: number;

  setRequestHeaders(headers: Record<string, string> | null): void {
    if (!headers) {
      return;
    }
    const normalizedHeaders: Record<string, string> = {};
    for (const [key, value] of Object.entries(headers)) {
      normalizedHeaders[key.toLowerCase()] = value;
    }
    this.requestHeaders = normalizedHeaders;
  }

  getRequestHeaders(): Record<string, string> | null | undefined {
    return this.requestHeaders;
  }

  constructor(params: MCPConnectionParams) {
    super();
    this.options = params.serverConfig;
    this.serverName = params.serverName;
    this.userId = params.userId;
    this.useSSRFProtection = params.useSSRFProtection === true;
    this.iconPath = params.serverConfig.iconPath;
    this.timeout = params.serverConfig.timeout;
    this.lastPingTime = Date.now();
    this.createdAt = Date.now(); // Record creation timestamp for staleness detection
    if (params.oauthTokens) {
      this.oauthTokens = params.oauthTokens;
    }
    this.client = new Client(
      {
        name: '@librechat/api-client',
        version: '1.2.3',
      },
      {
        capabilities: {},
      },
    );

    this.setupEventListeners();
  }

  /** Helper to generate consistent log prefixes */
  private getLogPrefix(): string {
    const userPart = this.userId ? `[User: ${this.userId}]` : '';
    return `[MCP]${userPart}[${this.serverName}]`;
  }

  /**
   * Factory function to create fetch functions without capturing the entire `this` context.
   * This helps prevent memory leaks by only passing necessary dependencies.
   *
   * @param getHeaders Function to retrieve request headers
   * @param timeout Timeout value for the agent (in milliseconds)
   * @returns A fetch function that merges headers appropriately
   */
  private createFetchFunction(
    getHeaders: () => Record<string, string> | null | undefined,
    timeout?: number,
  ): (input: UndiciRequestInfo, init?: UndiciRequestInit) => Promise<UndiciResponse> {
    const ssrfConnect = this.useSSRFProtection ? createSSRFSafeUndiciConnect() : undefined;
    const effectiveTimeout = timeout || DEFAULT_TIMEOUT;
    const agent = new Agent({
      bodyTimeout: effectiveTimeout,
      headersTimeout: effectiveTimeout,
      ...(ssrfConnect != null ? { connect: ssrfConnect } : {}),
    });
    this.agents.push(agent);

    return function customFetch(
      input: UndiciRequestInfo,
      init?: UndiciRequestInit,
    ): Promise<UndiciResponse> {
      const requestHeaders = getHeaders();
      if (!requestHeaders) {
        return undiciFetch(input, { ...init, dispatcher: agent });
      }

      let initHeaders: Record<string, string> = {};
      if (init?.headers) {
        if (init.headers instanceof Headers) {
          initHeaders = Object.fromEntries(init.headers.entries());
        } else if (Array.isArray(init.headers)) {
          initHeaders = Object.fromEntries(init.headers);
        } else {
          initHeaders = init.headers as Record<string, string>;
        }
      }

      return undiciFetch(input, {
        ...init,
        headers: {
          ...initHeaders,
          ...requestHeaders,
        },
        dispatcher: agent,
      });
    };
  }

  private emitError(error: unknown, errorContext: string): void {
    const errorMessage = error instanceof Error ? error.message : String(error);
    logger.error(`${this.getLogPrefix()} ${errorContext}: ${errorMessage}`);
  }

  private async constructTransport(options: t.MCPOptions): Promise<Transport> {
    try {
      let type: t.MCPOptions['type'];
      if (isStdioOptions(options)) {
        type = 'stdio';
      } else if (isWebSocketOptions(options)) {
        type = 'websocket';
      } else if (isStreamableHTTPOptions(options)) {
        // Could be either 'streamable-http' or 'http', normalize to 'streamable-http'
        type = 'streamable-http';
      } else if (isSSEOptions(options)) {
        type = 'sse';
      } else {
        throw new Error(
          'Cannot infer transport type: options.type is not provided and cannot be inferred from other properties.',
        );
      }

      switch (type) {
        case 'stdio':
          if (!isStdioOptions(options)) {
            throw new Error('Invalid options for stdio transport.');
          }
          return new StdioClientTransport({
            command: options.command,
            args: options.args,
            // workaround bug of mcp sdk that can't pass env:
            // https://github.com/modelcontextprotocol/typescript-sdk/issues/216
            env: { ...getDefaultEnvironment(), ...(options.env ?? {}) },
          });

        case 'websocket':
          if (!isWebSocketOptions(options)) {
            throw new Error('Invalid options for websocket transport.');
          }
          this.url = options.url;
          if (this.useSSRFProtection) {
            const wsHostname = new URL(options.url).hostname;
            const isSSRF = await resolveHostnameSSRF(wsHostname);
            if (isSSRF) {
              throw new Error(
                `SSRF protection: WebSocket host "${wsHostname}" resolved to a private/reserved IP address`,
              );
            }
          }
          return new WebSocketClientTransport(new URL(options.url));

        case 'sse': {
          if (!isSSEOptions(options)) {
            throw new Error('Invalid options for sse transport.');
          }
          this.url = options.url;
          const url = new URL(options.url);
          logger.info(
            `${this.getLogPrefix()} Creating SSE transport: ${sanitizeUrlForLogging(url)}`,
          );
          const abortController = new AbortController();

          /** Add OAuth token to headers if available */
          const headers = { ...options.headers };
          if (this.oauthTokens?.access_token) {
            headers['Authorization'] = `Bearer ${this.oauthTokens.access_token}`;
          }

          /**
           * SSE connections need longer timeouts for reliability.
           * The connect timeout is extended because proxies may delay initial response.
           */
          const sseTimeout = this.timeout || SSE_CONNECT_TIMEOUT;
          const ssrfConnect = this.useSSRFProtection ? createSSRFSafeUndiciConnect() : undefined;
          const sseAgent = new Agent({
            bodyTimeout: sseTimeout,
            headersTimeout: sseTimeout,
            keepAliveTimeout: sseTimeout,
            keepAliveMaxTimeout: sseTimeout * 2,
            ...(ssrfConnect != null ? { connect: ssrfConnect } : {}),
          });
          this.agents.push(sseAgent);
          const transport = new SSEClientTransport(url, {
            requestInit: {
              /** User/OAuth headers override SSE defaults */
              headers: { ...SSE_REQUEST_HEADERS, ...headers },
              signal: abortController.signal,
            },
            eventSourceInit: {
              fetch: (url, init) => {
                /** Merge headers: SSE defaults < init headers < user headers (user wins) */
                const fetchHeaders = new Headers(
                  Object.assign({}, SSE_REQUEST_HEADERS, init?.headers, headers),
                );
                return undiciFetch(url, {
                  ...init,
                  dispatcher: sseAgent,
                  headers: fetchHeaders,
                });
              },
            },
            fetch: this.createFetchFunction(
              this.getRequestHeaders.bind(this),
              sseTimeout,
            ) as unknown as FetchLike,
          });

          transport.onclose = () => {
            logger.info(`${this.getLogPrefix()} SSE transport closed`);
            this.emit('connectionChange', 'disconnected');
          };

          transport.onmessage = (message) => {
            logger.info(`${this.getLogPrefix()} Message received: ${JSON.stringify(message)}`);
          };

          this.setupTransportErrorHandlers(transport);
          return transport;
        }

        case 'streamable-http': {
          if (!isStreamableHTTPOptions(options)) {
            throw new Error('Invalid options for streamable-http transport.');
          }
          this.url = options.url;
          const url = new URL(options.url);
          logger.info(
            `${this.getLogPrefix()} Creating streamable-http transport: ${sanitizeUrlForLogging(url)}`,
          );
          const abortController = new AbortController();

          /** Add OAuth token to headers if available */
          const headers = { ...options.headers };
          if (this.oauthTokens?.access_token) {
            headers['Authorization'] = `Bearer ${this.oauthTokens.access_token}`;
          }

          const transport = new StreamableHTTPClientTransport(url, {
            requestInit: {
              headers,
              signal: abortController.signal,
            },
            fetch: this.createFetchFunction(
              this.getRequestHeaders.bind(this),
              this.timeout,
            ) as unknown as FetchLike,
          });

          transport.onclose = () => {
            logger.info(`${this.getLogPrefix()} Streamable-http transport closed`);
            this.emit('connectionChange', 'disconnected');
          };

          transport.onmessage = (message: JSONRPCMessage) => {
            logger.info(`${this.getLogPrefix()} Message received: ${JSON.stringify(message)}`);
          };

          this.setupTransportErrorHandlers(transport);
          return transport;
        }

        default: {
          throw new Error(`Unsupported transport type: ${type}`);
        }
      }
    } catch (error) {
      this.emitError(error, 'Failed to construct transport');
      throw error;
    }
  }

  private setupEventListeners(): void {
    this.isInitializing = true;
    this.on('connectionChange', (state: t.ConnectionState) => {
      this.connectionState = state;
      if (state === 'connected') {
        this.isReconnecting = false;
        this.isInitializing = false;
        this.shouldStopReconnecting = false;
        this.reconnectAttempts = 0;
        /**
         * // FOR DEBUGGING
         * // this.client.setRequestHandler(PingRequestSchema, async (request, extra) => {
         * //    logger.info(`[MCP][${this.serverName}] PingRequest: ${JSON.stringify(request)}`);
         * //    if (getEventListeners && extra.signal) {
         * //      const listenerCount = getEventListeners(extra.signal, 'abort').length;
         * //      logger.debug(`Signal has ${listenerCount} abort listeners`);
         * //    }
         * //    return {};
         * //  });
         */
      } else if (state === 'error' && !this.isReconnecting && !this.isInitializing) {
        this.handleReconnection().catch((error) => {
          logger.error(`${this.getLogPrefix()} Reconnection handler failed:`, error);
        });
      }
    });

    this.subscribeToResources();
  }

  private async handleReconnection(): Promise<void> {
    if (
      this.isReconnecting ||
      this.shouldStopReconnecting ||
      this.isInitializing ||
      this.oauthRequired
    ) {
      if (this.oauthRequired) {
        logger.info(`${this.getLogPrefix()} OAuth required, skipping reconnection attempts`);
      }
      return;
    }

    this.isReconnecting = true;
    const backoffDelay = (attempt: number) => {
      const base = Math.min(1000 * Math.pow(2, attempt), 30000);
      const jitter = Math.floor(Math.random() * 1000); // up to 1s of random jitter
      return base + jitter;
    };

    try {
      while (
        this.reconnectAttempts < this.MAX_RECONNECT_ATTEMPTS &&
        !(this.shouldStopReconnecting as boolean)
      ) {
        this.reconnectAttempts++;
        const delay = backoffDelay(this.reconnectAttempts);

        logger.info(
          `${this.getLogPrefix()} Reconnecting ${this.reconnectAttempts}/${this.MAX_RECONNECT_ATTEMPTS} (delay: ${delay}ms)`,
        );

        await new Promise((resolve) => setTimeout(resolve, delay));

        try {
          await this.connect();
          this.reconnectAttempts = 0;
          return;
        } catch (error) {
          logger.error(`${this.getLogPrefix()} Reconnection attempt failed:`, error);

          // Stop immediately if rate limited - retrying will only make it worse
          if (this.isRateLimitError(error)) {
            /**
             * Rate limiting sets shouldStopReconnecting to prevent hammering the server.
             * Silent return here (vs throw in connectClient) because we're already in
             * error recovery mode - throwing would just add noise. The connection
             * must be recreated to retry after rate limit lifts.
             */
            logger.warn(
              `${this.getLogPrefix()} Rate limited (429), stopping reconnection attempts`,
            );
            logger.debug(
              `${this.getLogPrefix()} Rate limit block is permanent for this connection instance`,
            );
            this.shouldStopReconnecting = true;
            return;
          }

          if (
            this.reconnectAttempts === this.MAX_RECONNECT_ATTEMPTS ||
            (this.shouldStopReconnecting as boolean)
          ) {
            logger.error(`${this.getLogPrefix()} Stopping reconnection attempts`);
            return;
          }
        }
      }
    } finally {
      this.isReconnecting = false;
    }
  }

  private subscribeToResources(): void {
    this.client.setNotificationHandler(ResourceListChangedNotificationSchema, async () => {
      this.emit('resourcesChanged');
    });
  }

  async connectClient(): Promise<void> {
    if (this.connectionState === 'connected') {
      return;
    }

    if (this.connectPromise) {
      return this.connectPromise;
    }

    if (this.shouldStopReconnecting) {
      return;
    }

    this.emit('connectionChange', 'connecting');

    this.connectPromise = (async () => {
      try {
        if (this.transport) {
          try {
            await this.client.close();
          } catch (error) {
            logger.warn(`${this.getLogPrefix()} Error closing connection:`, error);
          }
          this.transport = null;
          await this.closeAgents();
        }

        this.transport = await this.constructTransport(this.options);
        this.setupTransportDebugHandlers();

        const connectTimeout = this.options.initTimeout ?? 120000;
        await withTimeout(
          this.client.connect(this.transport),
          connectTimeout,
          `Connection timeout after ${connectTimeout}ms`,
        );

        this.connectionState = 'connected';
        this.emit('connectionChange', 'connected');
        this.reconnectAttempts = 0;
      } catch (error) {
        // Check if it's a rate limit error - stop immediately to avoid making it worse
        if (this.isRateLimitError(error)) {
          /**
           * Rate limiting sets shouldStopReconnecting to prevent hammering the server.
           * This is a permanent block for this connection instance - the connection
           * must be recreated (e.g., by user re-initiating) to retry after rate limit lifts.
           *
           * We throw here (unlike handleReconnection which returns silently) because:
           * - connectClient() is a public API - callers expect async errors to throw
           * - Other errors in this catch block also throw for consistency
           * - handleReconnection is private/internal error recovery, different context
           */
          logger.warn(`${this.getLogPrefix()} Rate limited (429), stopping connection attempts`);
          this.shouldStopReconnecting = true;
          this.connectionState = 'error';
          this.emit('connectionChange', 'error');
          throw error;
        }

        // Check if it's an OAuth authentication error
        if (this.isOAuthError(error)) {
          logger.warn(`${this.getLogPrefix()} OAuth authentication required`);
          this.oauthRequired = true;
          const serverUrl = this.url;
          logger.debug(
            `${this.getLogPrefix()} Server URL for OAuth: ${serverUrl ? sanitizeUrlForLogging(serverUrl) : 'undefined'}`,
          );

          const oauthTimeout = this.options.initTimeout ?? 60000 * 2;
          /** Promise that will resolve when OAuth is handled */
          const oauthHandledPromise = new Promise<void>((resolve, reject) => {
            let timeoutId: NodeJS.Timeout | null = null;
            let oauthHandledListener: (() => void) | null = null;
            let oauthFailedListener: ((error: Error) => void) | null = null;

            /** Cleanup function to remove listeners and clear timeout */
            const cleanup = () => {
              if (timeoutId) {
                clearTimeout(timeoutId);
              }
              if (oauthHandledListener) {
                this.off('oauthHandled', oauthHandledListener);
              }
              if (oauthFailedListener) {
                this.off('oauthFailed', oauthFailedListener);
              }
            };

            // Success handler
            oauthHandledListener = () => {
              cleanup();
              resolve();
            };

            // Failure handler
            oauthFailedListener = (error: Error) => {
              cleanup();
              reject(error);
            };

            // Timeout handler
            timeoutId = setTimeout(() => {
              cleanup();
              reject(new Error(`OAuth handling timeout after ${oauthTimeout}ms`));
            }, oauthTimeout);

            // Listen for both success and failure events
            this.once('oauthHandled', oauthHandledListener);
            this.once('oauthFailed', oauthFailedListener);
          });

          // Emit the event
          this.emit('oauthRequired', {
            serverName: this.serverName,
            error,
            serverUrl,
            userId: this.userId,
          });

          try {
            // Wait for OAuth to be handled
            await oauthHandledPromise;
            // Reset the oauthRequired flag
            this.oauthRequired = false;
            // Don't throw the error - just return so connection can be retried
            logger.info(
              `${this.getLogPrefix()} OAuth handled successfully, connection will be retried`,
            );
            return;
          } catch (oauthError) {
            // OAuth failed or timed out
            this.oauthRequired = false;
            logger.error(`${this.getLogPrefix()} OAuth handling failed:`, oauthError);
            // Re-throw the original authentication error
            throw error;
          }
        }

        this.connectionState = 'error';
        this.emit('connectionChange', 'error');
        throw error;
      } finally {
        this.connectPromise = null;
      }
    })();

    return this.connectPromise;
  }

  private setupTransportDebugHandlers(): void {
    if (!this.transport) {
      return;
    }

    this.transport.onmessage = (msg) => {
      logger.debug(`${this.getLogPrefix()} Transport received: ${JSON.stringify(msg)}`);
    };

    const originalSend = this.transport.send.bind(this.transport);
    this.transport.send = async (msg) => {
      if ('result' in msg && !('method' in msg) && Object.keys(msg.result ?? {}).length === 0) {
        if (Date.now() - this.lastPingTime < FIVE_MINUTES) {
          throw new Error('Empty result');
        }
        this.lastPingTime = Date.now();
      }
      logger.debug(`${this.getLogPrefix()} Transport sending: ${JSON.stringify(msg)}`);
      return originalSend(msg);
    };
  }

  async connect(): Promise<void> {
    try {
      await this.disconnect();
      await this.connectClient();
      if (!(await this.isConnected())) {
        throw new Error('Connection not established');
      }
    } catch (error) {
      logger.error(`${this.getLogPrefix()} Connection failed:`, error);
      throw error;
    }
  }

  private setupTransportErrorHandlers(transport: Transport): void {
    transport.onerror = (error) => {
      // Extract meaningful error information (handles "SSE error: undefined" cases)
      const {
        message: errorMessage,
        code: errorCode,
        isProxyHint,
        isTransient,
      } = extractSSEErrorMessage(error);

      if (errorCode === 404) {
        const hasSession =
          'sessionId' in transport &&
          (transport as { sessionId?: string }).sessionId != null &&
          (transport as { sessionId?: string }).sessionId !== '';

        if (!hasSession && errorMessage.toLowerCase().includes('failed to open sse stream')) {
          logger.warn(
            `${this.getLogPrefix()} SSE stream not available (404), no session. Ignoring.`,
          );
          return;
        }

        if (hasSession) {
          logger.warn(
            `${this.getLogPrefix()} 404 with active session — session lost, triggering reconnection.`,
          );
        }
      }

      // Check if it's an OAuth authentication error
      if (this.isOAuthError(error)) {
        logger.warn(`${this.getLogPrefix()} OAuth authentication error detected`);
        this.emit('oauthError', error);
      }

      /**
       * Log with enhanced context for debugging.
       * All transport.onerror events are logged as errors to preserve stack traces.
       * isTransient indicates whether auto-reconnection is expected to succeed.
       *
       * The MCP SDK's SseError extends Error and includes:
       * - code: HTTP status code or eventsource error code
       * - event: The original eventsource ErrorEvent
       * - stack: Full stack trace
       */
      const errorContext: Record<string, unknown> = {
        code: errorCode,
        isTransient,
      };

      if (isProxyHint) {
        errorContext.hint = 'Check Nginx/proxy configuration for SSE endpoints';
      }

      // Extract additional debug info from SseError if available
      if (error && typeof error === 'object') {
        const sseError = error as { event?: unknown; stack?: string };

        // Include the original eventsource event for debugging
        if (sseError.event && typeof sseError.event === 'object') {
          const event = sseError.event as { code?: number; message?: string; type?: string };
          errorContext.eventDetails = {
            type: event.type,
            code: event.code,
            message: event.message,
          };
        }

        // Include stack trace if available
        if (sseError.stack) {
          errorContext.stack = sseError.stack;
        }
      }

      const errorLabel = isTransient
        ? 'Transport error (transient, will reconnect)'
        : 'Transport error (may require manual intervention)';

      logger.error(`${this.getLogPrefix()} ${errorLabel}: ${errorMessage}`, errorContext);

      this.emit('connectionChange', 'error');
    };
  }

  private async closeAgents(): Promise<void> {
    const logPrefix = this.getLogPrefix();
    const closing = this.agents.map((agent) =>
      agent.close().catch((err: unknown) => {
        logger.debug(`${logPrefix} Agent close error (non-fatal):`, err);
      }),
    );
    this.agents = [];
    await Promise.all(closing);
  }

  public async disconnect(): Promise<void> {
    try {
      if (this.transport) {
        await this.client.close();
        this.transport = null;
      }
      await this.closeAgents();
      if (this.connectionState === 'disconnected') {
        return;
      }
      this.connectionState = 'disconnected';
      this.emit('connectionChange', 'disconnected');
    } finally {
      this.connectPromise = null;
    }
  }

  async fetchResources(): Promise<t.MCPResource[]> {
    try {
      const { resources } = await this.client.listResources();
      return resources;
    } catch (error) {
      this.emitError(error, 'Failed to fetch resources');
      return [];
    }
  }

  async fetchTools() {
    try {
      const { tools } = await this.client.listTools();
      return tools;
    } catch (error) {
      this.emitError(error, 'Failed to fetch tools');
      return [];
    }
  }

  async fetchPrompts(): Promise<t.MCPPrompt[]> {
    try {
      const { prompts } = await this.client.listPrompts();
      return prompts;
    } catch (error) {
      this.emitError(error, 'Failed to fetch prompts');
      return [];
    }
  }

  public async isConnected(): Promise<boolean> {
    // First check if we're in a connected state
    if (this.connectionState !== 'connected') {
      return false;
    }

    // If we recently checked, skip expensive verification
    const now = Date.now();
    if (now - this.lastConnectionCheckAt < mcpConfig.CONNECTION_CHECK_TTL) {
      return true;
    }
    this.lastConnectionCheckAt = now;

    try {
      // Try ping first as it's the lightest check
      await this.client.ping();
      return this.connectionState === 'connected';
    } catch (error) {
      // Check if the error is because ping is not supported (method not found)
      const pingUnsupported =
        error instanceof Error &&
        ((error as Error)?.message.includes('-32601') ||
          (error as Error)?.message.includes('-32602') ||
          (error as Error)?.message.includes('invalid method ping') ||
          (error as Error)?.message.includes('Unsupported method: ping') ||
          (error as Error)?.message.includes('method not found'));

      if (!pingUnsupported) {
        logger.error(`${this.getLogPrefix()} Ping failed:`, error);
        return false;
      }

      // Ping is not supported by this server, try an alternative verification
      logger.debug(
        `${this.getLogPrefix()} Server does not support ping method, verifying connection with capabilities`,
      );

      try {
        // Get server capabilities to verify connection is truly active
        const capabilities = this.client.getServerCapabilities();

        // If we have capabilities, try calling a supported method to verify connection
        if (capabilities?.tools) {
          await this.client.listTools();
          return this.connectionState === 'connected';
        } else if (capabilities?.resources) {
          await this.client.listResources();
          return this.connectionState === 'connected';
        } else if (capabilities?.prompts) {
          await this.client.listPrompts();
          return this.connectionState === 'connected';
        } else {
          // No capabilities to test, but we're in connected state and initialization succeeded
          logger.debug(
            `${this.getLogPrefix()} No capabilities to test, assuming connected based on state`,
          );
          return this.connectionState === 'connected';
        }
      } catch (capabilityError) {
        // If capability check fails, the connection is likely broken
        logger.error(`${this.getLogPrefix()} Connection verification failed:`, capabilityError);
        return false;
      }
    }
  }

  public setOAuthTokens(tokens: MCPOAuthTokens): void {
    this.oauthTokens = tokens;
  }

  /**
   * Check if this connection is stale compared to config update time.
   * A connection is stale if it was created before the config was updated.
   *
   * @param configUpdatedAt - Unix timestamp (ms) when config was last updated
   * @returns true if connection was created before config update, false otherwise
   */
  public isStale(configUpdatedAt: number): boolean {
    return this.createdAt < configUpdatedAt;
  }

  private isOAuthError(error: unknown): boolean {
    if (!error || typeof error !== 'object') {
      return false;
    }

    // Check for error code
    if ('code' in error) {
      const code = (error as { code?: number }).code;
      if (code === 401 || code === 403) {
        return true;
      }
    }

    // Check message for various auth error indicators
    if ('message' in error && typeof error.message === 'string') {
      const message = error.message.toLowerCase();
      // Check for 401 status
      if (message.includes('401') || message.includes('non-200 status code (401)')) {
        return true;
      }
      // Check for invalid_token (OAuth servers return this for expired/revoked tokens)
      if (message.includes('invalid_token')) {
        return true;
      }
      // Check for invalid_grant (OAuth servers return this for expired/revoked grants)
      if (message.includes('invalid_grant')) {
        return true;
      }
      // Check for authentication required
      if (message.includes('authentication required') || message.includes('unauthorized')) {
        return true;
      }
    }

    return false;
  }

  /**
   * Checks if an error indicates rate limiting (HTTP 429).
   * Rate limited requests should stop reconnection attempts to avoid making the situation worse.
   */
  private isRateLimitError(error: unknown): boolean {
    if (!error || typeof error !== 'object') {
      return false;
    }

    // Check for error code
    if ('code' in error) {
      const code = (error as { code?: number }).code;
      if (code === 429) {
        return true;
      }
    }

    // Check message for rate limit indicators
    if ('message' in error && typeof error.message === 'string') {
      const message = error.message.toLowerCase();
      if (
        message.includes('429') ||
        message.includes('rate limit') ||
        message.includes('too many requests')
      ) {
        return true;
      }
    }

    return false;
  }
}