feat(PortProxy): Enhancements to connection management in PortProxy

changelog.md

@@ -1,5 +1,15 @@
 # Changelog
 
+## 2025-03-03 - 3.21.0 - feat(PortProxy)
+Enhancements to connection management in PortProxy
+
+- Introduced a unique ID for each connection record for improved tracking.
+- Enhanced cleanup mechanism for connections with dual states: initiated and executed.
+- Implemented shutdown process handling to ensure graceful connection closure.
+- Added logging for better tracing of connection activities and states.
+- Improved connection setup with explicit timeouts and data flow management.
+- Integrated inactivity and parity checks to monitor connection health.
+
 ## 2025-03-01 - 3.20.2 - fix(PortProxy)
 Enhance connection cleanup handling in PortProxy
 

ts/00_commitinfo_data.ts

@@ -3,6 +3,6 @@
  */
 export const commitinfo = {
   name: '@push.rocks/smartproxy',
-  version: '3.20.2',
+  version: '3.21.0',
   description: 'A powerful proxy package that effectively handles high traffic, with features such as SSL/TLS support, port proxying, WebSocket handling, and dynamic routing with authentication options.'
 }

ts/classes.portproxy.ts

@@ -22,6 +22,7 @@ export interface IPortProxySettings extends plugins.tls.TlsOptions {
   maxConnectionLifetime?: number; // (ms) force cleanup of long-lived connections
   globalPortRanges: Array<{ from: number; to: number }>; // Global allowed port ranges
   forwardAllGlobalRanges?: boolean; // When true, forwards all connections on global port ranges to the global targetIP
+  gracefulShutdownTimeout?: number; // (ms) maximum time to wait for connections to close during shutdown
 }
 
 /**
@@ -93,9 +94,12 @@ interface IConnectionRecord {
   incomingStartTime: number;
   outgoingStartTime?: number;
   outgoingClosedTime?: number;
-  lockedDomain?: string; // New field to lock this connection to the initial SNI
+  lockedDomain?: string; // Field to lock this connection to the initial SNI
   connectionClosed: boolean;
   cleanupTimer?: NodeJS.Timeout; // Timer to force cleanup after max lifetime/inactivity
+  cleanupInitiated: boolean; // Flag to track if cleanup has been initiated but not completed
+  id: string; // Unique identifier for the connection
+  lastActivity: number; // Timestamp of last activity on either socket
 }
 
 // Helper: Check if a port falls within any of the given port ranges.
@@ -128,12 +132,18 @@ const isGlobIPAllowed = (ip: string, allowed: string[], blocked: string[] = []):
   return isAllowed(ip, allowed);
 };
 
+// Helper: Generate a unique ID for a connection
+const generateConnectionId = (): string => {
+  return Math.random().toString(36).substring(2, 15) + Math.random().toString(36).substring(2, 15);
+};
+
 export class PortProxy {
   private netServers: plugins.net.Server[] = [];
   settings: IPortProxySettings;
   // Unified record tracking each connection pair.
-  private connectionRecords: Set<IConnectionRecord> = new Set();
+  private connectionRecords: Map<string, IConnectionRecord> = new Map();
   private connectionLogger: NodeJS.Timeout | null = null;
+  private isShuttingDown: boolean = false;
 
   // Map to track round robin indices for each domain config.
   private domainTargetIndices: Map<IDomainConfig, number> = new Map();
@@ -151,6 +161,7 @@ export class PortProxy {
       ...settingsArg,
       targetIP: settingsArg.targetIP || 'localhost',
       maxConnectionLifetime: settingsArg.maxConnectionLifetime || 600000,
+      gracefulShutdownTimeout: settingsArg.gracefulShutdownTimeout || 30000,
     };
   }
 
@@ -159,30 +170,77 @@ export class PortProxy {
   }
 
   /**
-   * Cleans up a connection record if not already cleaned up.
+   * Initiates the cleanup process for a connection.
-   * Destroys both incoming and outgoing sockets, clears timers, and removes the record.
+   * Sets the flag to prevent duplicate cleanup attempts and schedules actual cleanup.
-   * Logs the cleanup event.
    */
-  private cleanupConnection(record: IConnectionRecord, special: boolean = false): void {
+  private initiateCleanup(record: IConnectionRecord, reason: string = 'normal'): void {
-    if (!record.connectionClosed) {
+    if (record.cleanupInitiated) return;
+    
+    record.cleanupInitiated = true;
+    const remoteIP = record.incoming.remoteAddress || 'unknown';
+    console.log(`Initiating cleanup for connection ${record.id} from ${remoteIP} (reason: ${reason})`);
+    
+    // Execute cleanup immediately to prevent lingering connections
+    this.executeCleanup(record);
+  }
+
+  /**
+   * Executes the actual cleanup of a connection.
+   * Destroys sockets, clears timers, and removes the record.
+   */
+  private executeCleanup(record: IConnectionRecord): void {
+    if (record.connectionClosed) return;
+    
     record.connectionClosed = true;
+    const remoteIP = record.incoming.remoteAddress || 'unknown';
+    
     if (record.cleanupTimer) {
       clearTimeout(record.cleanupTimer);
+      record.cleanupTimer = undefined;
     }
+    
+    // End the sockets first to allow for graceful closure
+    try {
+      if (!record.incoming.destroyed) {
+        record.incoming.end();
+        // Set a safety timeout to force destroy if end doesn't complete
+        setTimeout(() => {
+          if (!record.incoming.destroyed) {
+            console.log(`Forcing destruction of incoming socket for ${remoteIP}`);
+            record.incoming.destroy();
+          }
+        }, 1000);
+      }
+    } catch (err) {
+      console.error(`Error ending incoming socket for ${remoteIP}:`, err);
       if (!record.incoming.destroyed) {
         record.incoming.destroy();
       }
+    }
+
+    try {
+      if (record.outgoing && !record.outgoing.destroyed) {
+        record.outgoing.end();
+        // Set a safety timeout to force destroy if end doesn't complete
+        setTimeout(() => {
+          if (record.outgoing && !record.outgoing.destroyed) {
+            console.log(`Forcing destruction of outgoing socket for ${remoteIP}`);
+            record.outgoing.destroy();
+          }
+        }, 1000);
+      }
+    } catch (err) {
+      console.error(`Error ending outgoing socket for ${remoteIP}:`, err);
       if (record.outgoing && !record.outgoing.destroyed) {
         record.outgoing.destroy();
       }
-      this.connectionRecords.delete(record);
-      const remoteIP = record.incoming.remoteAddress || 'unknown';
-      if (special) {
-        console.log(`Special parity cleanup: Connection from ${remoteIP} cleaned up due to duration difference.`);
-      } else {
-        console.log(`Connection from ${remoteIP} terminated. Active connections: ${this.connectionRecords.size}`);
-      }
     }
+
+    // Remove the record after a delay to ensure all events have propagated
+    setTimeout(() => {
+      this.connectionRecords.delete(record.id);
+      console.log(`Connection ${record.id} from ${remoteIP} fully cleaned up. Active connections: ${this.connectionRecords.size}`);
+    }, 2000);
   }
 
   private getTargetIP(domainConfig: IDomainConfig): string {
@@ -195,27 +253,60 @@ export class PortProxy {
     return this.settings.targetIP!;
   }
 
+  /**
+   * Updates the last activity timestamp for a connection record
+   */
+  private updateActivity(record: IConnectionRecord): void {
+    record.lastActivity = Date.now();
+    
+    // Reset the inactivity timer if one is set
+    if (this.settings.maxConnectionLifetime && record.cleanupTimer) {
+      clearTimeout(record.cleanupTimer);
+      
+      // Set a new cleanup timer
+      record.cleanupTimer = setTimeout(() => {
+        const now = Date.now();
+        const inactivityTime = now - record.lastActivity;
+        const remoteIP = record.incoming.remoteAddress || 'unknown';
+        console.log(`Connection ${record.id} from ${remoteIP} exceeded max lifetime or inactivity period (${inactivityTime}ms), forcing cleanup.`);
+        this.initiateCleanup(record, 'timeout');
+      }, this.settings.maxConnectionLifetime);
+    }
+  }
+
   public async start() {
     // Define a unified connection handler for all listening ports.
     const connectionHandler = (socket: plugins.net.Socket) => {
+      if (this.isShuttingDown) {
+        socket.end();
+        socket.destroy();
+        return;
+      }
+
       const remoteIP = socket.remoteAddress || '';
       const localPort = socket.localPort; // The port on which this connection was accepted.
+      
+      const connectionId = generateConnectionId();
       const connectionRecord: IConnectionRecord = {
+        id: connectionId,
         incoming: socket,
         outgoing: null,
         incomingStartTime: Date.now(),
+        lastActivity: Date.now(),
         connectionClosed: false,
+        cleanupInitiated: false
       };
-      this.connectionRecords.add(connectionRecord);
+
-      console.log(`New connection from ${remoteIP} on port ${localPort}. Active connections: ${this.connectionRecords.size}`);
+      this.connectionRecords.set(connectionId, connectionRecord);
+      console.log(`New connection ${connectionId} from ${remoteIP} on port ${localPort}. Active connections: ${this.connectionRecords.size}`);
 
       let initialDataReceived = false;
       let incomingTerminationReason: string | null = null;
       let outgoingTerminationReason: string | null = null;
 
       // Local cleanup function that delegates to the class method.
-      const cleanupOnce = () => {
+      const initiateCleanupOnce = (reason: string = 'normal') => {
-        this.cleanupConnection(connectionRecord);
+        this.initiateCleanup(connectionRecord, reason);
       };
 
       // Helper to reject an incoming connection.
@@ -226,14 +317,31 @@ export class PortProxy {
           incomingTerminationReason = reason;
           this.incrementTerminationStat('incoming', reason);
         }
-        cleanupOnce();
+        initiateCleanupOnce(reason);
       };
 
+      // Set an initial timeout immediately
+      const initialTimeout = setTimeout(() => {
+        if (!initialDataReceived) {
+          console.log(`Initial connection timeout for ${remoteIP} (no data received)`);
+          if (incomingTerminationReason === null) {
+            incomingTerminationReason = 'initial_timeout';
+            this.incrementTerminationStat('incoming', 'initial_timeout');
+          }
+          initiateCleanupOnce('initial_timeout');
+        }
+      }, 5000);
+
       socket.on('error', (err: Error) => {
         const errorMessage = initialDataReceived
           ? `(Immediate) Incoming socket error from ${remoteIP}: ${err.message}`
           : `(Premature) Incoming socket error from ${remoteIP} before data received: ${err.message}`;
         console.log(errorMessage);
+        
+        // Clear the initial timeout if it exists
+        if (initialTimeout) {
+          clearTimeout(initialTimeout);
+        }
       });
 
       const handleError = (side: 'incoming' | 'outgoing') => (err: Error) => {
@@ -242,9 +350,13 @@ export class PortProxy {
         if (code === 'ECONNRESET') {
           reason = 'econnreset';
           console.log(`ECONNRESET on ${side} side from ${remoteIP}: ${err.message}`);
+        } else if (code === 'ECONNREFUSED') {
+          reason = 'econnrefused';
+          console.log(`ECONNREFUSED on ${side} side from ${remoteIP}: ${err.message}`);
         } else {
           console.log(`Error on ${side} side from ${remoteIP}: ${err.message}`);
         }
+        
         if (side === 'incoming' && incomingTerminationReason === null) {
           incomingTerminationReason = reason;
           this.incrementTerminationStat('incoming', reason);
@@ -252,11 +364,13 @@ export class PortProxy {
           outgoingTerminationReason = reason;
           this.incrementTerminationStat('outgoing', reason);
         }
-        cleanupOnce();
+        
+        initiateCleanupOnce(reason);
       };
 
       const handleClose = (side: 'incoming' | 'outgoing') => () => {
         console.log(`Connection closed on ${side} side from ${remoteIP}`);
+        
         if (side === 'incoming' && incomingTerminationReason === null) {
           incomingTerminationReason = 'normal';
           this.incrementTerminationStat('incoming', 'normal');
@@ -265,8 +379,24 @@ export class PortProxy {
           this.incrementTerminationStat('outgoing', 'normal');
           // Record the time when outgoing socket closed.
           connectionRecord.outgoingClosedTime = Date.now();
+          
+          // If incoming is still active but outgoing closed, set a shorter timeout
+          if (!connectionRecord.incoming.destroyed) {
+            console.log(`Outgoing socket closed but incoming still active for ${remoteIP}. Setting cleanup timeout.`);
+            setTimeout(() => {
+              if (!connectionRecord.connectionClosed && !connectionRecord.incoming.destroyed) {
+                console.log(`Incoming socket still active ${Date.now() - connectionRecord.outgoingClosedTime!}ms after outgoing closed for ${remoteIP}. Cleaning up.`);
+                initiateCleanupOnce('outgoing_closed_timeout');
+              }
+            }, 10000); // 10 second timeout instead of waiting for the next parity check
+          }
+        }
+        
+        // If both sides are closed/destroyed, clean up
+        if ((side === 'incoming' && connectionRecord.outgoing?.destroyed) || 
+            (side === 'outgoing' && connectionRecord.incoming.destroyed)) {
+          initiateCleanupOnce('both_closed');
         }
-        cleanupOnce();
       };
 
       /**
@@ -274,9 +404,14 @@ export class PortProxy {
        * @param serverName - The SNI hostname (unused when forcedDomain is provided).
        * @param initialChunk - Optional initial data chunk.
        * @param forcedDomain - If provided, overrides SNI/domain lookup (used for port-based routing).
-       * @param overridePort - If provided, use this port for the outgoing connection (typically the same as the incoming port).
+       * @param overridePort - If provided, use this port for the outgoing connection.
        */
       const setupConnection = (serverName: string, initialChunk?: Buffer, forcedDomain?: IDomainConfig, overridePort?: number) => {
+        // Clear the initial timeout since we've received data
+        if (initialTimeout) {
+          clearTimeout(initialTimeout);
+        }
+        
         // If a forcedDomain is provided (port-based routing), use it; otherwise, use SNI-based lookup.
         const domainConfig = forcedDomain
           ? forcedDomain
@@ -297,10 +432,13 @@ export class PortProxy {
           if (!isGlobIPAllowed(remoteIP, effectiveAllowedIPs, effectiveBlockedIPs)) {
             return rejectIncomingConnection('rejected', `Connection rejected: IP ${remoteIP} not allowed for domain ${domainConfig.domains.join(', ')}`);
           }
-        } else if (this.settings.defaultAllowedIPs) {
+        } else if (this.settings.defaultAllowedIPs && this.settings.defaultAllowedIPs.length > 0) {
           if (!isGlobIPAllowed(remoteIP, this.settings.defaultAllowedIPs, this.settings.defaultBlockedIPs || [])) {
             return rejectIncomingConnection('rejected', `Connection rejected: IP ${remoteIP} not allowed by default allowed list`);
           }
+        } else {
+          // No domain config and no default allowed IPs - reject the connection
+          return rejectIncomingConnection('no_config', `Connection rejected: No matching domain configuration or default allowed IPs for ${remoteIP}`);
         }
 
         const targetHost = domainConfig ? this.getTargetIP(domainConfig) : this.settings.targetIP!;
@@ -312,88 +450,127 @@ export class PortProxy {
           connectionOptions.localAddress = remoteIP.replace('::ffff:', '');
         }
 
+        // Add explicit connection timeout and error handling
+        let connectionTimeout: NodeJS.Timeout | null = null;
+        let connectionSucceeded = false;
+        
+        // Set connection timeout
+        connectionTimeout = setTimeout(() => {
+          if (!connectionSucceeded) {
+            console.log(`Connection timeout connecting to ${targetHost}:${connectionOptions.port} for ${remoteIP}`);
+            if (outgoingTerminationReason === null) {
+              outgoingTerminationReason = 'connection_timeout';
+              this.incrementTerminationStat('outgoing', 'connection_timeout');
+            }
+            initiateCleanupOnce('connection_timeout');
+          }
+        }, 5000);
+
+        console.log(`Attempting to connect to ${targetHost}:${connectionOptions.port} for client ${remoteIP}...`);
+        
+        // Create the target socket
         const targetSocket = plugins.net.connect(connectionOptions);
         connectionRecord.outgoing = targetSocket;
-        connectionRecord.outgoingStartTime = Date.now();
         
+        // Handle successful connection
+        targetSocket.once('connect', () => {
+          connectionSucceeded = true;
+          if (connectionTimeout) {
+            clearTimeout(connectionTimeout);
+            connectionTimeout = null;
+          }
+          
+          connectionRecord.outgoingStartTime = Date.now();
           console.log(
             `Connection established: ${remoteIP} -> ${targetHost}:${connectionOptions.port}` +
             `${serverName ? ` (SNI: ${serverName})` : forcedDomain ? ` (Port-based for domain: ${forcedDomain.domains.join(', ')})` : ''}`
           );
 
+          // Setup data flow after confirmed connection
+          setupDataFlow(targetSocket, initialChunk);
+        });
+
+        // Handle connection errors early
+        targetSocket.once('error', (err) => {
+          if (!connectionSucceeded) {
+            // This is an initial connection error
+            console.log(`Failed to connect to ${targetHost}:${connectionOptions.port} for ${remoteIP}: ${err.message}`);
+            if (connectionTimeout) {
+              clearTimeout(connectionTimeout);
+              connectionTimeout = null;
+            }
+            if (outgoingTerminationReason === null) {
+              outgoingTerminationReason = 'connection_failed';
+              this.incrementTerminationStat('outgoing', 'connection_failed');
+            }
+            initiateCleanupOnce('connection_failed');
+          }
+          // Other errors will be handled by the main error handler
+        });
+      };
+
+      /**
+       * Sets up the data flow between sockets after successful connection
+       */
+      const setupDataFlow = (targetSocket: plugins.net.Socket, initialChunk?: Buffer) => {
         if (initialChunk) {
           socket.unshift(initialChunk);
         }
+        
+        // Set appropriate timeouts for both sockets
         socket.setTimeout(120000);
+        targetSocket.setTimeout(120000);
+        
+        // Set up the pipe in both directions
         socket.pipe(targetSocket);
         targetSocket.pipe(socket);
 
-        // Attach error and close handlers.
+        // Attach error and close handlers
         socket.on('error', handleError('incoming'));
         targetSocket.on('error', handleError('outgoing'));
         socket.on('close', handleClose('incoming'));
         targetSocket.on('close', handleClose('outgoing'));
+        
+        // Handle timeout events
         socket.on('timeout', () => {
           console.log(`Timeout on incoming side from ${remoteIP}`);
           if (incomingTerminationReason === null) {
             incomingTerminationReason = 'timeout';
             this.incrementTerminationStat('incoming', 'timeout');
           }
-          cleanupOnce();
+          initiateCleanupOnce('timeout');
         });
+        
         targetSocket.on('timeout', () => {
           console.log(`Timeout on outgoing side from ${remoteIP}`);
           if (outgoingTerminationReason === null) {
             outgoingTerminationReason = 'timeout';
             this.incrementTerminationStat('outgoing', 'timeout');
           }
-          cleanupOnce();
+          initiateCleanupOnce('timeout');
         });
+        
         socket.on('end', handleClose('incoming'));
         targetSocket.on('end', handleClose('outgoing'));
 
-        // Initialize a cleanup timer for max connection lifetime.
+        // Track activity for both sockets to reset inactivity timers
+        socket.on('data', (data) => {
+          this.updateActivity(connectionRecord);
+        });
+        
+        targetSocket.on('data', (data) => {
+          this.updateActivity(connectionRecord);
+        });
+
+        // Initialize a cleanup timer for max connection lifetime
         if (this.settings.maxConnectionLifetime) {
-          // Flags to track if data was seen from each side.
-          let incomingActive = false;
-          let outgoingActive = false;
-          const resetCleanupTimer = () => {
-            if (this.settings.maxConnectionLifetime) {
-              if (connectionRecord.cleanupTimer) {
-                clearTimeout(connectionRecord.cleanupTimer);
-              }
           connectionRecord.cleanupTimer = setTimeout(() => {
-                console.log(`Connection from ${remoteIP} exceeded max lifetime with inactivity (${this.settings.maxConnectionLifetime}ms), forcing cleanup.`);
+            console.log(`Connection from ${remoteIP} exceeded max lifetime (${this.settings.maxConnectionLifetime}ms), forcing cleanup.`);
-                cleanupOnce();
+            initiateCleanupOnce('max_lifetime');
           }, this.settings.maxConnectionLifetime);
         }
       };
 
-          resetCleanupTimer();
-
-          // Only reset the timer if outgoing socket is still active.
-          socket.on('data', () => {
-            incomingActive = true;
-            // Check if outgoing has not been closed before resetting timer.
-            if (!connectionRecord.outgoingClosedTime && incomingActive && outgoingActive) {
-              resetCleanupTimer();
-              incomingActive = false;
-              outgoingActive = false;
-            }
-          });
-          targetSocket.on('data', () => {
-            // If outgoing is closed, do not set outgoingActive.
-            if (connectionRecord.outgoingClosedTime) return;
-            outgoingActive = true;
-            if (incomingActive && outgoingActive) {
-              resetCleanupTimer();
-              incomingActive = false;
-              outgoingActive = false;
-            }
-          });
-        }
-      };
-
       // --- PORT RANGE-BASED HANDLING ---
       // Only apply port-based rules if the incoming port is within one of the global port ranges.
       if (this.settings.globalPortRanges && isPortInRanges(localPort, this.settings.globalPortRanges)) {
@@ -401,6 +578,7 @@ export class PortProxy {
           if (this.settings.defaultAllowedIPs && !isAllowed(remoteIP, this.settings.defaultAllowedIPs)) {
             console.log(`Connection from ${remoteIP} rejected: IP ${remoteIP} not allowed in global default allowed list.`);
             socket.end();
+            initiateCleanupOnce('rejected');
             return;
           }
           console.log(`Port-based connection from ${remoteIP} on port ${localPort} forwarded to global target IP ${this.settings.targetIP}.`);
@@ -429,6 +607,7 @@ export class PortProxy {
             if (!isGlobIPAllowed(remoteIP, effectiveAllowedIPs, effectiveBlockedIPs)) {
               console.log(`Connection from ${remoteIP} rejected: IP not allowed for domain ${forcedDomain.domains.join(', ')} on port ${localPort}.`);
               socket.end();
+              initiateCleanupOnce('rejected');
               return;
             }
             console.log(`Port-based connection from ${remoteIP} on port ${localPort} matched domain ${forcedDomain.domains.join(', ')}.`);
@@ -441,32 +620,36 @@ export class PortProxy {
 
       // --- FALLBACK: SNI-BASED HANDLING (or default when SNI is disabled) ---
       if (this.settings.sniEnabled) {
-        socket.setTimeout(5000, () => {
+        initialDataReceived = false;
-          console.log(`Initial data timeout for ${remoteIP}`);
-          socket.end();
-          cleanupOnce();
-        });
 
         socket.once('data', (chunk: Buffer) => {
-          socket.setTimeout(0);
           initialDataReceived = true;
           const serverName = extractSNI(chunk) || '';
           // Lock the connection to the negotiated SNI.
           connectionRecord.lockedDomain = serverName;
           console.log(`Received connection from ${remoteIP} with SNI: ${serverName}`);
+          
           // Delay adding the renegotiation listener until the next tick,
           // so the initial ClientHello is not reprocessed.
           setImmediate(() => {
             socket.on('data', (renegChunk: Buffer) => {
               if (renegChunk.length > 0 && renegChunk.readUInt8(0) === 22) {
+                try {
+                  // Try to extract SNI from potential renegotiation
                   const newSNI = extractSNI(renegChunk);
                   if (newSNI && newSNI !== connectionRecord.lockedDomain) {
                     console.log(`Rehandshake detected with different SNI: ${newSNI} vs locked ${connectionRecord.lockedDomain}. Terminating connection.`);
-                  cleanupOnce();
+                    initiateCleanupOnce('sni_mismatch');
+                  } else if (newSNI) {
+                    console.log(`Rehandshake detected with same SNI: ${newSNI}. Allowing.`);
+                  }
+                } catch (err) {
+                  console.log(`Error processing potential renegotiation: ${err}. Allowing connection to continue.`);
                 }
               }
             });
           });
+          
           setupConnection(serverName, chunk);
         });
       } else {
@@ -507,23 +690,48 @@ export class PortProxy {
       this.netServers.push(server);
     }
 
-    // Log active connection count, longest running durations, and run parity checks every 10 seconds.
+    // Log active connection count, run parity checks, and check for connection issues every 10 seconds.
     this.connectionLogger = setInterval(() => {
+      if (this.isShuttingDown) return;
+      
       const now = Date.now();
       let maxIncoming = 0;
       let maxOutgoing = 0;
-      for (const record of this.connectionRecords) {
+      
+      // Create a copy of the keys to avoid modification during iteration
+      const connectionIds = [...this.connectionRecords.keys()];
+      
+      for (const id of connectionIds) {
+        const record = this.connectionRecords.get(id);
+        if (!record) continue;
+        
         maxIncoming = Math.max(maxIncoming, now - record.incomingStartTime);
         if (record.outgoingStartTime) {
           maxOutgoing = Math.max(maxOutgoing, now - record.outgoingStartTime);
         }
-        // Parity check: if outgoing socket closed and incoming remains active for >1 minute, trigger special cleanup.
+        
-        if (record.outgoingClosedTime && !record.incoming.destroyed && (now - record.outgoingClosedTime > 60000)) {
+        // Parity check: if outgoing socket closed and incoming remains active for >30 seconds, trigger cleanup
+        if (record.outgoingClosedTime && 
+            !record.incoming.destroyed && 
+            !record.connectionClosed && 
+            !record.cleanupInitiated && 
+            (now - record.outgoingClosedTime > 30000)) {
           const remoteIP = record.incoming.remoteAddress || 'unknown';
-          console.log(`Parity check triggered: Incoming socket for ${remoteIP} has been active >1 minute after outgoing closed.`);
+          console.log(`Parity check triggered: Incoming socket for ${remoteIP} has been active >30s after outgoing closed.`);
-          this.cleanupConnection(record, true);
+          this.initiateCleanup(record, 'parity_check');
+        }
+        
+        // Inactivity check: if no activity for a long time but sockets still open
+        const inactivityTime = now - record.lastActivity;
+        if (inactivityTime > 180000 && // 3 minutes
+            !record.connectionClosed && 
+            !record.cleanupInitiated) {
+          const remoteIP = record.incoming.remoteAddress || 'unknown';
+          console.log(`Inactivity check triggered: No activity on connection from ${remoteIP} for ${plugins.prettyMs(inactivityTime)}.`);
+          this.initiateCleanup(record, 'inactivity');
         }
       }
+      
       console.log(
         `(Interval Log) Active connections: ${this.connectionRecords.size}. ` +
         `Longest running incoming: ${plugins.prettyMs(maxIncoming)}, outgoing: ${plugins.prettyMs(maxOutgoing)}. ` +
@@ -534,17 +742,69 @@ export class PortProxy {
   }
 
   public async stop() {
-    // Close all servers.
+    console.log("PortProxy shutting down...");
-    const closePromises: Promise<void>[] = this.netServers.map(
+    this.isShuttingDown = true;
+    
+    // Stop accepting new connections
+    const closeServerPromises: Promise<void>[] = this.netServers.map(
       server =>
         new Promise<void>((resolve) => {
           server.close(() => resolve());
         })
     );
+    
+    // Stop the connection logger
     if (this.connectionLogger) {
       clearInterval(this.connectionLogger);
       this.connectionLogger = null;
     }
-    await Promise.all(closePromises);
+
+    // Wait for servers to close
+    await Promise.all(closeServerPromises);
+    console.log("All servers closed. Cleaning up active connections...");
+    
+    // Gracefully close active connections
+    const connectionIds = [...this.connectionRecords.keys()];
+    console.log(`Cleaning up ${connectionIds.length} active connections...`);
+    
+    for (const id of connectionIds) {
+      const record = this.connectionRecords.get(id);
+      if (record && !record.connectionClosed && !record.cleanupInitiated) {
+        this.initiateCleanup(record, 'shutdown');
+      }
+    }
+    
+    // Wait for graceful shutdown or timeout
+    const shutdownTimeout = this.settings.gracefulShutdownTimeout || 30000;
+    await new Promise<void>((resolve) => {
+      const checkInterval = setInterval(() => {
+        if (this.connectionRecords.size === 0) {
+          clearInterval(checkInterval);
+          resolve();
+        }
+      }, 1000);
+      
+      // Force resolve after timeout
+      setTimeout(() => {
+        clearInterval(checkInterval);
+        if (this.connectionRecords.size > 0) {
+          console.log(`Forcing shutdown with ${this.connectionRecords.size} connections still active`);
+          
+          // Force destroy any remaining connections
+          for (const record of this.connectionRecords.values()) {
+            if (!record.incoming.destroyed) {
+              record.incoming.destroy();
+            }
+            if (record.outgoing && !record.outgoing.destroyed) {
+              record.outgoing.destroy();
+            }
+          }
+          this.connectionRecords.clear();
+        }
+        resolve();
+      }, shutdownTimeout);
+    });
+    
+    console.log("PortProxy shutdown complete.");
   }
 }