19.5.18

- Updated socket handling to prevent connection accumulation in chained proxies.
- Introduced centralized bidirectional forwarding for consistent socket management.
- Enhanced cleanup logic to ensure immediate closure of sockets when one closes.
- Added tests to verify connection behavior under various scenarios, including backend failures and rapid reconnections.

certs/static-route/meta.json

@@ -1,5 +1,5 @@
 {
-  "expiryDate": "2025-08-29T18:29:48.329Z",
-  "issueDate": "2025-05-31T18:29:48.329Z",
-  "savedAt": "2025-05-31T18:29:48.330Z"
+  "expiryDate": "2025-08-30T08:11:10.101Z",
+  "issueDate": "2025-06-01T08:11:10.101Z",
+  "savedAt": "2025-06-01T08:11:10.102Z"
 }

package.json

@@ -1,6 +1,6 @@
 {
   "name": "@push.rocks/smartproxy",
-  "version": "19.5.6",
+  "version": "19.5.18",
   "private": false,
   "description": "A powerful proxy package with unified route-based configuration for high traffic management. Features include SSL/TLS support, flexible routing patterns, WebSocket handling, advanced security options, and automatic ACME certificate management.",
   "main": "dist_ts/index.js",

readme.hints.md

@@ -413,4 +413,231 @@ const routes: IRouteConfig[] = [{
 ### 7. Next Steps (Remaining Work)
 - **Phase 2 (cont)**: Migrate components to use LifecycleComponent
 - **Phase 3**: Add worker threads for CPU-intensive operations  
-- **Phase 4**: Performance monitoring dashboard
+- **Phase 4**: Performance monitoring dashboard
+
+## Socket Error Handling Fix (v19.5.11+)
+
+### Issue
+Server crashed with unhandled 'error' event when backend connections failed (ECONNREFUSED). Also caused memory leak with rising active connection count as failed connections weren't cleaned up properly.
+
+### Root Cause
+1. **Race Condition**: In forwarding handlers, sockets were created with `net.connect()` but error handlers were attached later, creating a window where errors could crash the server
+2. **Incomplete Cleanup**: When server connections failed, client sockets weren't properly cleaned up, leaving connection records in memory
+
+### Solution
+Created `createSocketWithErrorHandler()` utility that attaches error handlers immediately:
+```typescript
+// Before (race condition):
+const socket = net.connect(port, host);
+// ... other code ...
+socket.on('error', handler); // Too late!
+
+// After (safe):
+const socket = createSocketWithErrorHandler({
+  port, host,
+  onError: (error) => {
+    // Handle error immediately
+    clientSocket.destroy();
+  },
+  onConnect: () => {
+    // Set up forwarding
+  }
+});
+```
+
+### Changes Made
+1. **New Utility**: `ts/core/utils/socket-utils.ts` - Added `createSocketWithErrorHandler()`
+2. **Updated Handlers**:
+   - `https-passthrough-handler.ts` - Uses safe socket creation
+   - `https-terminate-to-http-handler.ts` - Uses safe socket creation
+3. **Connection Cleanup**: Client sockets destroyed immediately on server connection failure
+
+### Test Coverage
+- `test/test.socket-error-handling.node.ts` - Verifies server doesn't crash on ECONNREFUSED
+- `test/test.forwarding-error-fix.node.ts` - Tests forwarding handlers handle errors gracefully
+
+### Configuration
+No configuration changes needed. The fix is transparent to users.
+
+### Important Note
+The fix was applied in two places:
+1. **ForwardingHandler classes** (`https-passthrough-handler.ts`, etc.) - These are standalone forwarding utilities
+2. **SmartProxy route-connection-handler** (`route-connection-handler.ts`) - This is where the actual SmartProxy connection handling happens
+
+The critical fix for SmartProxy was in `setupDirectConnection()` method in route-connection-handler.ts, which now uses `createSocketWithErrorHandler()` to properly handle connection failures and clean up connection records.
+
+## Connection Cleanup Improvements (v19.5.12+)
+
+### Issue
+Connections were still counting up during rapid retry scenarios, especially when routing failed or backend connections were refused. This was due to:
+1. **Delayed Cleanup**: Using `initiateCleanupOnce` queued cleanup operations (batch of 100 every 100ms) instead of immediate cleanup
+2. **NFTables Memory Leak**: NFTables connections were never cleaned up, staying in memory forever
+3. **Connection Limit Bypass**: When max connections reached, connection record check happened after creation
+
+### Root Cause Analysis
+1. **Queued vs Immediate Cleanup**:
+   - `initiateCleanupOnce()`: Adds to cleanup queue, processes up to 100 connections every 100ms
+   - `cleanupConnection()`: Immediate synchronous cleanup
+   - Under rapid retries, connections were created faster than the queue could process them
+
+2. **NFTables Connections**: 
+   - Marked with `usingNetworkProxy = true` but never cleaned up
+   - Connection records stayed in memory indefinitely
+
+3. **Error Path Cleanup**:
+   - Many error paths used `socket.end()` (async) followed by cleanup
+   - Created timing windows where connections weren't fully cleaned
+
+### Solution
+1. **Immediate Cleanup**: Changed all error paths from `initiateCleanupOnce()` to `cleanupConnection()` for immediate cleanup
+2. **NFTables Cleanup**: Added socket close listener to clean up connection records when NFTables connections close
+3. **Connection Limit Fix**: Added null check after `createConnection()` to handle rejection properly
+
+### Changes Made in route-connection-handler.ts
+```typescript
+// 1. NFTables cleanup (line 551-553)
+socket.once('close', () => {
+  this.connectionManager.cleanupConnection(record, 'nftables_closed');
+});
+
+// 2. Connection limit check (line 93-96)
+const record = this.connectionManager.createConnection(socket);
+if (!record) {
+  // Connection was rejected due to limit - socket already destroyed
+  return;
+}
+
+// 3. Changed all error paths to use immediate cleanup
+// Before: this.connectionManager.initiateCleanupOnce(record, reason)
+// After: this.connectionManager.cleanupConnection(record, reason)
+```
+
+### Test Coverage
+- `test/test.rapid-retry-cleanup.node.ts` - Verifies connection cleanup under rapid retry scenarios
+- Test shows connection count stays at 0 even with 20 rapid retries with 50ms intervals
+- Confirms both ECONNREFUSED and routing failure scenarios are handled correctly
+
+### Performance Impact
+- **Positive**: No more connection accumulation under load
+- **Positive**: Immediate cleanup reduces memory usage
+- **Consideration**: More frequent cleanup operations, but prevents queue backlog
+
+### Migration Notes
+No configuration changes needed. The improvements are automatic and backward compatible.
+
+## Early Client Disconnect Handling (v19.5.13+)
+
+### Issue
+Connections were accumulating when clients connected but disconnected before sending data or during routing. This occurred in two scenarios:
+1. **TLS Path**: Clients connecting and disconnecting before sending initial TLS handshake data
+2. **Non-TLS Immediate Routing**: Clients disconnecting while backend connection was being established
+
+### Root Cause
+1. **Missing Cleanup Handlers**: During initial data wait and immediate routing, no close/end handlers were attached to catch early disconnections
+2. **Race Condition**: Backend connection attempts continued even after client disconnected, causing unhandled errors
+3. **Timing Window**: Between accepting connection and establishing full bidirectional flow, disconnections weren't properly handled
+
+### Solution
+1. **TLS Path Fix**: Added close/end handlers during initial data wait (lines 224-253 in route-connection-handler.ts)
+2. **Immediate Routing Fix**: Used `setupSocketHandlers` for proper handler attachment (lines 180-205)
+3. **Backend Error Handling**: Check if connection already closed before handling backend errors (line 1144)
+
+### Changes Made
+```typescript
+// 1. TLS path - handle disconnect before initial data
+socket.once('close', () => {
+  if (!initialDataReceived) {
+    this.connectionManager.cleanupConnection(record, 'closed_before_data');
+  }
+});
+
+// 2. Immediate routing path - proper handler setup
+setupSocketHandlers(socket, (reason) => {
+  if (!record.outgoing || record.outgoing.readyState !== 'open') {
+    if (record.outgoing && !record.outgoing.destroyed) {
+      record.outgoing.destroy(); // Abort pending backend connection
+    }
+    this.connectionManager.cleanupConnection(record, reason);
+  }
+}, undefined, 'immediate-route-client');
+
+// 3. Backend connection error handling
+onError: (error) => {
+  if (record.connectionClosed) {
+    logger.log('debug', 'Backend connection failed but client already disconnected');
+    return; // Client already gone, nothing to clean up
+  }
+  // ... normal error handling
+}
+```
+
+### Test Coverage
+- `test/test.connect-disconnect-cleanup.node.ts` - Comprehensive test for early disconnect scenarios
+- Tests verify connection count stays at 0 even with rapid connect/disconnect patterns
+- Covers immediate disconnect, delayed disconnect, and mixed patterns
+
+### Performance Impact
+- **Positive**: No more connection accumulation from early disconnects
+- **Positive**: Immediate cleanup reduces memory usage
+- **Positive**: Prevents resource exhaustion from rapid reconnection attempts
+
+### Migration Notes
+No configuration changes needed. The fix is automatic and backward compatible.
+
+## Proxy Chain Connection Accumulation Fix (v19.5.14+)
+
+### Issue
+When chaining SmartProxies (Client → SmartProxy1 → SmartProxy2 → Backend), connections would accumulate and never be cleaned up. This was particularly severe when the backend was down or closing connections immediately.
+
+### Root Cause
+The half-open connection support was preventing proper cascade cleanup in proxy chains:
+1. Backend closes → SmartProxy2's server socket closes
+2. SmartProxy2 keeps client socket open (half-open support)
+3. SmartProxy1 never gets notified that downstream is closed
+4. Connections accumulate at each proxy in the chain
+
+The issue was in `createIndependentSocketHandlers()` which waited for BOTH sockets to close before cleanup.
+
+### Solution
+1. **Changed default behavior**: When one socket closes, both close immediately
+2. **Made half-open support opt-in**: Only enabled when explicitly requested
+3. **Centralized socket handling**: Created `setupBidirectionalForwarding()` for consistent behavior
+4. **Applied everywhere**: Updated HttpProxyBridge and route-connection-handler to use centralized handling
+
+### Changes Made
+```typescript
+// socket-utils.ts - Default behavior now closes both sockets
+export function createIndependentSocketHandlers(
+  clientSocket, serverSocket, onBothClosed,
+  options: { enableHalfOpen?: boolean } = {} // Half-open is opt-in
+) {
+  // When server closes, immediately close client (unless half-open enabled)
+  if (!clientClosed && !options.enableHalfOpen) {
+    clientSocket.destroy();
+  }
+}
+
+// New centralized function for consistent socket pairing
+export function setupBidirectionalForwarding(
+  clientSocket, serverSocket,
+  handlers: {
+    onClientData?: (chunk) => void;
+    onServerData?: (chunk) => void;
+    onCleanup: (reason) => void;
+    enableHalfOpen?: boolean; // Default: false
+  }
+)
+```
+
+### Test Coverage
+- `test/test.proxy-chain-simple.node.ts` - Verifies proxy chains don't accumulate connections
+- Tests confirm connections stay at 0 even with backend closing immediately
+- Works for any proxy chain configuration (not just localhost)
+
+### Performance Impact
+- **Positive**: No more connection accumulation in proxy chains
+- **Positive**: Immediate cleanup reduces memory usage
+- **Neutral**: Half-open connections still available when needed (opt-in)
+
+### Migration Notes
+No configuration changes needed. The fix applies to all proxy chains automatically.

test/core/utils/test.lifecycle-component.ts

@@ -249,4 +249,4 @@ tap.test('should not create timers when shutting down', async () => {
   expect(intervalFired).toBeFalse();
 });
 
-tap.start();
+export default tap.start();

test/test.connect-disconnect-cleanup.node.ts

@@ -0,0 +1,242 @@
+import { tap, expect } from '@git.zone/tstest/tapbundle';
+import * as net from 'net';
+import * as plugins from '../ts/plugins.js';
+
+// Import SmartProxy and configurations
+import { SmartProxy } from '../ts/index.js';
+
+tap.test('should handle clients that connect and immediately disconnect without sending data', async () => {
+  console.log('\n=== Testing Connect-Disconnect Cleanup ===');
+  
+  // Create a SmartProxy instance
+  const proxy = new SmartProxy({
+    ports: [8560],
+    enableDetailedLogging: false,
+    initialDataTimeout: 5000, // 5 second timeout for initial data
+    routes: [{
+      name: 'test-route',
+      match: { ports: 8560 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 9999  // Non-existent port
+        }
+      }
+    }]
+  });
+  
+  // Start the proxy
+  await proxy.start();
+  console.log('✓ Proxy started on port 8560');
+  
+  // Helper to get active connection count
+  const getActiveConnections = () => {
+    const connectionManager = (proxy as any).connectionManager;
+    return connectionManager ? connectionManager.getConnectionCount() : 0;
+  };
+  
+  const initialCount = getActiveConnections();
+  console.log(`Initial connection count: ${initialCount}`);
+  
+  // Test 1: Connect and immediately disconnect without sending data
+  console.log('\n--- Test 1: Immediate disconnect ---');
+  const connectionCounts: number[] = [];
+  
+  for (let i = 0; i < 10; i++) {
+    const client = new net.Socket();
+    
+    // Connect and immediately destroy
+    client.connect(8560, 'localhost', () => {
+      // Connected - immediately destroy without sending data
+      client.destroy();
+    });
+    
+    // Wait a tiny bit
+    await new Promise(resolve => setTimeout(resolve, 10));
+    
+    const count = getActiveConnections();
+    connectionCounts.push(count);
+    if ((i + 1) % 5 === 0) {
+      console.log(`After ${i + 1} connect/disconnect cycles: ${count} active connections`);
+    }
+  }
+  
+  // Wait a bit for cleanup
+  await new Promise(resolve => setTimeout(resolve, 500));
+  
+  const afterImmediateDisconnect = getActiveConnections();
+  console.log(`After immediate disconnect test: ${afterImmediateDisconnect} active connections`);
+  
+  // Test 2: Connect, wait a bit, then disconnect without sending data
+  console.log('\n--- Test 2: Delayed disconnect ---');
+  
+  for (let i = 0; i < 5; i++) {
+    const client = new net.Socket();
+    
+    client.on('error', () => {
+      // Ignore errors
+    });
+    
+    client.connect(8560, 'localhost', () => {
+      // Wait 100ms then disconnect without sending data
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+      }, 100);
+    });
+  }
+  
+  // Check count immediately
+  const duringDelayed = getActiveConnections();
+  console.log(`During delayed disconnect test: ${duringDelayed} active connections`);
+  
+  // Wait for cleanup
+  await new Promise(resolve => setTimeout(resolve, 1000));
+  
+  const afterDelayedDisconnect = getActiveConnections();
+  console.log(`After delayed disconnect test: ${afterDelayedDisconnect} active connections`);
+  
+  // Test 3: Mix of immediate and delayed disconnects
+  console.log('\n--- Test 3: Mixed disconnect patterns ---');
+  
+  const promises = [];
+  for (let i = 0; i < 20; i++) {
+    promises.push(new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      
+      client.on('error', () => {
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(8560, 'localhost', () => {
+        if (i % 2 === 0) {
+          // Half disconnect immediately
+          client.destroy();
+        } else {
+          // Half wait 50ms
+          setTimeout(() => {
+            if (!client.destroyed) {
+              client.destroy();
+            }
+          }, 50);
+        }
+      });
+      
+      // Failsafe timeout
+      setTimeout(() => resolve(), 200);
+    }));
+  }
+  
+  // Wait for all to complete
+  await Promise.all(promises);
+  
+  const duringMixed = getActiveConnections();
+  console.log(`During mixed test: ${duringMixed} active connections`);
+  
+  // Final cleanup wait
+  await new Promise(resolve => setTimeout(resolve, 1000));
+  
+  const finalCount = getActiveConnections();
+  console.log(`\nFinal connection count: ${finalCount}`);
+  
+  // Stop the proxy
+  await proxy.stop();
+  console.log('✓ Proxy stopped');
+  
+  // Verify all connections were cleaned up
+  expect(finalCount).toEqual(initialCount);
+  expect(afterImmediateDisconnect).toEqual(initialCount);
+  expect(afterDelayedDisconnect).toEqual(initialCount);
+  
+  // Check that connections didn't accumulate during the test
+  const maxCount = Math.max(...connectionCounts);
+  console.log(`\nMax connection count during immediate disconnect test: ${maxCount}`);
+  expect(maxCount).toBeLessThan(3); // Should stay very low
+  
+  console.log('\n✅ PASS: Connect-disconnect cleanup working correctly!');
+});
+
+tap.test('should handle clients that error during connection', async () => {
+  console.log('\n=== Testing Connection Error Cleanup ===');
+  
+  const proxy = new SmartProxy({
+    ports: [8561],
+    enableDetailedLogging: false,
+    routes: [{
+      name: 'test-route',
+      match: { ports: 8561 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 9999
+        }
+      }
+    }]
+  });
+  
+  await proxy.start();
+  console.log('✓ Proxy started on port 8561');
+  
+  const getActiveConnections = () => {
+    const connectionManager = (proxy as any).connectionManager;
+    return connectionManager ? connectionManager.getConnectionCount() : 0;
+  };
+  
+  const initialCount = getActiveConnections();
+  console.log(`Initial connection count: ${initialCount}`);
+  
+  // Create connections that will error
+  const promises = [];
+  for (let i = 0; i < 10; i++) {
+    promises.push(new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      
+      client.on('error', () => {
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      // Connect to proxy
+      client.connect(8561, 'localhost', () => {
+        // Force an error by writing invalid data then destroying
+        try {
+          client.write(Buffer.alloc(1024 * 1024)); // Large write
+          client.destroy();
+        } catch (e) {
+          // Ignore
+        }
+      });
+      
+      // Timeout
+      setTimeout(() => resolve(), 500);
+    }));
+  }
+  
+  await Promise.all(promises);
+  console.log('✓ All error connections completed');
+  
+  // Wait for cleanup
+  await new Promise(resolve => setTimeout(resolve, 500));
+  
+  const finalCount = getActiveConnections();
+  console.log(`Final connection count: ${finalCount}`);
+  
+  await proxy.stop();
+  console.log('✓ Proxy stopped');
+  
+  expect(finalCount).toEqual(initialCount);
+  
+  console.log('\n✅ PASS: Connection error cleanup working correctly!');
+});
+
+tap.start();

test/test.connection-cleanup-comprehensive.node.ts

@@ -0,0 +1,279 @@
+import { tap, expect } from '@git.zone/tstest/tapbundle';
+import * as net from 'net';
+import * as plugins from '../ts/plugins.js';
+
+// Import SmartProxy and configurations
+import { SmartProxy } from '../ts/index.js';
+
+tap.test('comprehensive connection cleanup test - all scenarios', async () => {
+  console.log('\n=== Comprehensive Connection Cleanup Test ===');
+  
+  // Create a SmartProxy instance
+  const proxy = new SmartProxy({
+    ports: [8570, 8571], // One for immediate routing, one for TLS
+    enableDetailedLogging: false,
+    initialDataTimeout: 2000,
+    socketTimeout: 5000,
+    routes: [
+      {
+        name: 'non-tls-route',
+        match: { ports: 8570 },
+        action: {
+          type: 'forward',
+          target: {
+            host: 'localhost',
+            port: 9999  // Non-existent port
+          }
+        }
+      },
+      {
+        name: 'tls-route',
+        match: { ports: 8571 },
+        action: {
+          type: 'forward',
+          target: {
+            host: 'localhost',
+            port: 9999  // Non-existent port
+          },
+          tls: {
+            mode: 'passthrough'
+          }
+        }
+      }
+    ]
+  });
+  
+  // Start the proxy
+  await proxy.start();
+  console.log('✓ Proxy started on ports 8570 (non-TLS) and 8571 (TLS)');
+  
+  // Helper to get active connection count
+  const getActiveConnections = () => {
+    const connectionManager = (proxy as any).connectionManager;
+    return connectionManager ? connectionManager.getConnectionCount() : 0;
+  };
+  
+  const initialCount = getActiveConnections();
+  console.log(`Initial connection count: ${initialCount}`);
+  
+  // Test 1: Rapid ECONNREFUSED retries (from original issue)
+  console.log('\n--- Test 1: Rapid ECONNREFUSED retries ---');
+  for (let i = 0; i < 10; i++) {
+    await new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      
+      client.on('error', () => {
+        client.destroy();
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(8570, 'localhost', () => {
+        // Send data to trigger routing
+        client.write('GET / HTTP/1.1\r\nHost: test.com\r\n\r\n');
+      });
+      
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+        resolve();
+      }, 100);
+    });
+    
+    if ((i + 1) % 5 === 0) {
+      const count = getActiveConnections();
+      console.log(`After ${i + 1} ECONNREFUSED retries: ${count} active connections`);
+    }
+  }
+  
+  // Test 2: Connect without sending data (immediate disconnect)
+  console.log('\n--- Test 2: Connect without sending data ---');
+  for (let i = 0; i < 10; i++) {
+    const client = new net.Socket();
+    
+    client.on('error', () => {
+      // Ignore
+    });
+    
+    // Connect to non-TLS port and immediately disconnect
+    client.connect(8570, 'localhost', () => {
+      client.destroy();
+    });
+    
+    await new Promise(resolve => setTimeout(resolve, 10));
+  }
+  
+  const afterNoData = getActiveConnections();
+  console.log(`After connect-without-data test: ${afterNoData} active connections`);
+  
+  // Test 3: TLS connections that disconnect before handshake
+  console.log('\n--- Test 3: TLS early disconnect ---');
+  for (let i = 0; i < 10; i++) {
+    const client = new net.Socket();
+    
+    client.on('error', () => {
+      // Ignore
+    });
+    
+    // Connect to TLS port but disconnect before sending handshake
+    client.connect(8571, 'localhost', () => {
+      // Wait 50ms then disconnect (before initial data timeout)
+      setTimeout(() => {
+        client.destroy();
+      }, 50);
+    });
+    
+    await new Promise(resolve => setTimeout(resolve, 100));
+  }
+  
+  const afterTlsEarly = getActiveConnections();
+  console.log(`After TLS early disconnect test: ${afterTlsEarly} active connections`);
+  
+  // Test 4: Mixed pattern - simulating real-world chaos
+  console.log('\n--- Test 4: Mixed chaos pattern ---');
+  const promises = [];
+  
+  for (let i = 0; i < 30; i++) {
+    promises.push(new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      const port = i % 2 === 0 ? 8570 : 8571;
+      
+      client.on('error', () => {
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(port, 'localhost', () => {
+        const scenario = i % 5;
+        
+        switch (scenario) {
+          case 0:
+            // Immediate disconnect
+            client.destroy();
+            break;
+          case 1:
+            // Send data then disconnect
+            client.write('GET / HTTP/1.1\r\nHost: test.com\r\n\r\n');
+            setTimeout(() => client.destroy(), 20);
+            break;
+          case 2:
+            // Disconnect after delay
+            setTimeout(() => client.destroy(), 100);
+            break;
+          case 3:
+            // Send partial TLS handshake
+            if (port === 8571) {
+              client.write(Buffer.from([0x16, 0x03, 0x01])); // Partial TLS
+            }
+            setTimeout(() => client.destroy(), 50);
+            break;
+          case 4:
+            // Just let it timeout
+            break;
+        }
+      });
+      
+      // Failsafe
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+        resolve();
+      }, 500);
+    }));
+    
+    // Small delay between connections
+    if (i % 5 === 0) {
+      await new Promise(resolve => setTimeout(resolve, 10));
+    }
+  }
+  
+  await Promise.all(promises);
+  console.log('✓ Chaos test completed');
+  
+  // Wait for any cleanup
+  await new Promise(resolve => setTimeout(resolve, 1000));
+  
+  const afterChaos = getActiveConnections();
+  console.log(`After chaos test: ${afterChaos} active connections`);
+  
+  // Test 5: NFTables route (should cleanup properly)
+  console.log('\n--- Test 5: NFTables route cleanup ---');
+  const nftProxy = new SmartProxy({
+    ports: [8572],
+    enableDetailedLogging: false,
+    routes: [{
+      name: 'nftables-route',
+      match: { ports: 8572 },
+      action: {
+        type: 'forward',
+        forwardingEngine: 'nftables',
+        target: {
+          host: 'localhost',
+          port: 9999
+        }
+      }
+    }]
+  });
+  
+  await nftProxy.start();
+  
+  const getNftConnections = () => {
+    const connectionManager = (nftProxy as any).connectionManager;
+    return connectionManager ? connectionManager.getConnectionCount() : 0;
+  };
+  
+  // Create NFTables connections
+  for (let i = 0; i < 5; i++) {
+    const client = new net.Socket();
+    
+    client.on('error', () => {
+      // Ignore
+    });
+    
+    client.connect(8572, 'localhost', () => {
+      setTimeout(() => client.destroy(), 50);
+    });
+    
+    await new Promise(resolve => setTimeout(resolve, 100));
+  }
+  
+  await new Promise(resolve => setTimeout(resolve, 500));
+  
+  const nftFinal = getNftConnections();
+  console.log(`NFTables connections after test: ${nftFinal}`);
+  
+  await nftProxy.stop();
+  
+  // Final check on main proxy
+  const finalCount = getActiveConnections();
+  console.log(`\nFinal connection count: ${finalCount}`);
+  
+  // Stop the proxy
+  await proxy.stop();
+  console.log('✓ Proxy stopped');
+  
+  // Verify all connections were cleaned up
+  expect(finalCount).toEqual(initialCount);
+  expect(afterNoData).toEqual(initialCount);
+  expect(afterTlsEarly).toEqual(initialCount);
+  expect(afterChaos).toEqual(initialCount);
+  expect(nftFinal).toEqual(0);
+  
+  console.log('\n✅ PASS: Comprehensive connection cleanup test passed!');
+  console.log('All connection scenarios properly cleaned up:');
+  console.log('- ECONNREFUSED rapid retries');
+  console.log('- Connect without sending data');
+  console.log('- TLS early disconnect');
+  console.log('- Mixed chaos patterns');
+  console.log('- NFTables connections');
+});
+
+tap.start();

test/test.long-lived-connections.ts

@@ -0,0 +1,192 @@
+import { tap, expect } from '@git.zone/tstest/tapbundle';
+import * as net from 'net';
+import * as tls from 'tls';
+import { SmartProxy } from '../ts/index.js';
+
+let testProxy: SmartProxy;
+let targetServer: net.Server;
+
+// Create a simple echo server as target
+tap.test('setup test environment', async () => {
+  // Create target server that echoes data back
+  targetServer = net.createServer((socket) => {
+    console.log('Target server: client connected');
+    
+    // Echo data back
+    socket.on('data', (data) => {
+      console.log(`Target server received: ${data.toString().trim()}`);
+      socket.write(data);
+    });
+    
+    socket.on('close', () => {
+      console.log('Target server: client disconnected');
+    });
+  });
+  
+  await new Promise<void>((resolve) => {
+    targetServer.listen(9876, () => {
+      console.log('Target server listening on port 9876');
+      resolve();
+    });
+  });
+  
+  // Create proxy with simple TCP forwarding (no TLS)
+  testProxy = new SmartProxy({
+    routes: [{
+      name: 'tcp-forward-test',
+      match: {
+        ports: 8888  // Plain TCP port
+      },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 9876
+        }
+        // No TLS configuration - just plain TCP forwarding
+      }
+    }],
+    defaults: {
+      target: {
+        host: 'localhost',
+        port: 9876
+      }
+    },
+    enableDetailedLogging: true,
+    keepAliveTreatment: 'extended',  // Allow long-lived connections
+    inactivityTimeout: 3600000,      // 1 hour
+    socketTimeout: 3600000,          // 1 hour
+    keepAlive: true,
+    keepAliveInitialDelay: 1000
+  });
+  
+  await testProxy.start();
+});
+
+tap.test('should keep WebSocket-like connection open for extended period', async (tools) => {
+  tools.timeout(65000); // 65 second test timeout
+  
+  const client = new net.Socket();
+  let messagesReceived = 0;
+  let connectionClosed = false;
+  
+  // Connect to proxy
+  await new Promise<void>((resolve, reject) => {
+    client.connect(8888, 'localhost', () => {
+      console.log('Client connected to proxy');
+      resolve();
+    });
+    
+    client.on('error', reject);
+  });
+  
+  // Set up data handler
+  client.on('data', (data) => {
+    console.log(`Client received: ${data.toString().trim()}`);
+    messagesReceived++;
+  });
+  
+  client.on('close', () => {
+    console.log('Client connection closed');
+    connectionClosed = true;
+  });
+  
+  // Send initial handshake-like data
+  client.write('HELLO\n');
+  
+  // Wait for response
+  await new Promise(resolve => setTimeout(resolve, 100));
+  expect(messagesReceived).toEqual(1);
+  
+  // Simulate WebSocket-like keep-alive pattern
+  // Send periodic messages over 60 seconds
+  const startTime = Date.now();
+  const pingInterval = setInterval(() => {
+    if (!connectionClosed && Date.now() - startTime < 60000) {
+      console.log('Sending ping...');
+      client.write('PING\n');
+    } else {
+      clearInterval(pingInterval);
+    }
+  }, 10000); // Every 10 seconds
+  
+  // Wait for 61 seconds
+  await new Promise(resolve => setTimeout(resolve, 61000));
+  
+  // Clean up interval
+  clearInterval(pingInterval);
+  
+  // Connection should still be open
+  expect(connectionClosed).toEqual(false);
+  
+  // Should have received responses (1 hello + 6 pings)
+  expect(messagesReceived).toBeGreaterThan(5);
+  
+  // Close connection gracefully
+  client.end();
+  
+  // Wait for close
+  await new Promise(resolve => setTimeout(resolve, 100));
+  expect(connectionClosed).toEqual(true);
+});
+
+tap.test('should support half-open connections', async () => {
+  const client = new net.Socket();
+  const serverSocket = await new Promise<net.Socket>((resolve) => {
+    targetServer.once('connection', resolve);
+    client.connect(8888, 'localhost');
+  });
+  
+  let clientClosed = false;
+  let serverClosed = false;
+  let serverReceivedData = false;
+  
+  client.on('close', () => {
+    clientClosed = true;
+  });
+  
+  serverSocket.on('close', () => {
+    serverClosed = true;
+  });
+  
+  serverSocket.on('data', () => {
+    serverReceivedData = true;
+  });
+  
+  // Client sends data then closes write side
+  client.write('HALF-OPEN TEST\n');
+  client.end(); // Close write side only
+  
+  // Wait a bit
+  await new Promise(resolve => setTimeout(resolve, 500));
+  
+  // Server should still be able to send data
+  expect(serverClosed).toEqual(false);
+  serverSocket.write('RESPONSE\n');
+  
+  // Wait for data
+  await new Promise(resolve => setTimeout(resolve, 100));
+  
+  // Now close server side
+  serverSocket.end();
+  
+  // Wait for full close
+  await new Promise(resolve => setTimeout(resolve, 500));
+  
+  expect(clientClosed).toEqual(true);
+  expect(serverClosed).toEqual(true);
+  expect(serverReceivedData).toEqual(true);
+});
+
+tap.test('cleanup', async () => {
+  await testProxy.stop();
+  
+  await new Promise<void>((resolve) => {
+    targetServer.close(() => {
+      console.log('Target server closed');
+      resolve();
+    });
+  });
+});
+
+export default tap.start();

test/test.proxy-chain-simple.node.ts

@@ -0,0 +1,195 @@
+import { tap, expect } from '@git.zone/tstest/tapbundle';
+import * as net from 'net';
+import * as plugins from '../ts/plugins.js';
+
+// Import SmartProxy and configurations
+import { SmartProxy } from '../ts/index.js';
+
+tap.test('simple proxy chain test - identify connection accumulation', async () => {
+  console.log('\n=== Simple Proxy Chain Test ===');
+  console.log('Setup: Client → SmartProxy1 (8590) → SmartProxy2 (8591) → Backend (down)');
+  
+  // Create backend server that accepts and immediately closes connections
+  const backend = net.createServer((socket) => {
+    console.log('Backend: Connection received, closing immediately');
+    socket.destroy();
+  });
+  
+  await new Promise<void>((resolve) => {
+    backend.listen(9998, () => {
+      console.log('✓ Backend server started on port 9998 (closes connections immediately)');
+      resolve();
+    });
+  });
+  
+  // Create SmartProxy2 (downstream)
+  const proxy2 = new SmartProxy({
+    ports: [8591],
+    enableDetailedLogging: true,
+    socketTimeout: 5000,
+    routes: [{
+      name: 'to-backend',
+      match: { ports: 8591 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 9998  // Backend that closes immediately
+        }
+      }
+    }]
+  });
+  
+  // Create SmartProxy1 (upstream)
+  const proxy1 = new SmartProxy({
+    ports: [8590],
+    enableDetailedLogging: true,
+    socketTimeout: 5000,
+    routes: [{
+      name: 'to-proxy2',
+      match: { ports: 8590 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 8591  // Forward to proxy2
+        }
+      }
+    }]
+  });
+  
+  await proxy2.start();
+  console.log('✓ SmartProxy2 started on port 8591');
+  
+  await proxy1.start();
+  console.log('✓ SmartProxy1 started on port 8590');
+  
+  // Helper to get connection counts
+  const getConnectionCounts = () => {
+    const conn1 = (proxy1 as any).connectionManager;
+    const conn2 = (proxy2 as any).connectionManager;
+    return {
+      proxy1: conn1 ? conn1.getConnectionCount() : 0,
+      proxy2: conn2 ? conn2.getConnectionCount() : 0
+    };
+  };
+  
+  console.log('\n--- Making 5 sequential connections ---');
+  
+  for (let i = 0; i < 5; i++) {
+    console.log(`\n=== Connection ${i + 1} ===`);
+    
+    const counts = getConnectionCounts();
+    console.log(`Before: Proxy1=${counts.proxy1}, Proxy2=${counts.proxy2}`);
+    
+    await new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      let dataReceived = false;
+      
+      client.on('data', (data) => {
+        console.log(`Client received data: ${data.toString()}`);
+        dataReceived = true;
+      });
+      
+      client.on('error', (err) => {
+        console.log(`Client error: ${err.code}`);
+        resolve();
+      });
+      
+      client.on('close', () => {
+        console.log(`Client closed (data received: ${dataReceived})`);
+        resolve();
+      });
+      
+      client.connect(8590, 'localhost', () => {
+        console.log('Client connected to Proxy1');
+        // Send HTTP request
+        client.write('GET / HTTP/1.1\r\nHost: test.com\r\n\r\n');
+      });
+      
+      // Timeout
+      setTimeout(() => {
+        if (!client.destroyed) {
+          console.log('Client timeout, destroying');
+          client.destroy();
+        }
+        resolve();
+      }, 2000);
+    });
+    
+    // Wait a bit and check counts
+    await new Promise(resolve => setTimeout(resolve, 500));
+    
+    const afterCounts = getConnectionCounts();
+    console.log(`After: Proxy1=${afterCounts.proxy1}, Proxy2=${afterCounts.proxy2}`);
+    
+    if (afterCounts.proxy1 > 0 || afterCounts.proxy2 > 0) {
+      console.log('⚠️  WARNING: Connections not cleaned up!');
+    }
+  }
+  
+  console.log('\n--- Test with backend completely down ---');
+  
+  // Stop backend
+  backend.close();
+  await new Promise(resolve => setTimeout(resolve, 100));
+  console.log('✓ Backend stopped');
+  
+  // Make more connections with backend down
+  for (let i = 0; i < 3; i++) {
+    console.log(`\n=== Connection ${i + 6} (backend down) ===`);
+    
+    const counts = getConnectionCounts();
+    console.log(`Before: Proxy1=${counts.proxy1}, Proxy2=${counts.proxy2}`);
+    
+    await new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      
+      client.on('error', () => {
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(8590, 'localhost', () => {
+        client.write('GET / HTTP/1.1\r\nHost: test.com\r\n\r\n');
+      });
+      
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+        resolve();
+      }, 1000);
+    });
+    
+    await new Promise(resolve => setTimeout(resolve, 500));
+    
+    const afterCounts = getConnectionCounts();
+    console.log(`After: Proxy1=${afterCounts.proxy1}, Proxy2=${afterCounts.proxy2}`);
+  }
+  
+  // Final check
+  console.log('\n--- Final Check ---');
+  await new Promise(resolve => setTimeout(resolve, 1000));
+  
+  const finalCounts = getConnectionCounts();
+  console.log(`Final counts: Proxy1=${finalCounts.proxy1}, Proxy2=${finalCounts.proxy2}`);
+  
+  await proxy1.stop();
+  await proxy2.stop();
+  
+  // Verify
+  if (finalCounts.proxy1 > 0 || finalCounts.proxy2 > 0) {
+    console.log('\n❌ FAIL: Connections accumulated!');
+  } else {
+    console.log('\n✅ PASS: No connection accumulation');
+  }
+  
+  expect(finalCounts.proxy1).toEqual(0);
+  expect(finalCounts.proxy2).toEqual(0);
+});
+
+tap.start();

test/test.proxy-chaining-accumulation.node.ts

@@ -0,0 +1,368 @@
+import { tap, expect } from '@git.zone/tstest/tapbundle';
+import * as net from 'net';
+import * as plugins from '../ts/plugins.js';
+
+// Import SmartProxy and configurations
+import { SmartProxy } from '../ts/index.js';
+
+tap.test('should handle proxy chaining without connection accumulation', async () => {
+  console.log('\n=== Testing Proxy Chaining Connection Accumulation ===');
+  console.log('Setup: Client → SmartProxy1 → SmartProxy2 → Backend (down)');
+  
+  // Create SmartProxy2 (downstream proxy)
+  const proxy2 = new SmartProxy({
+    ports: [8581],
+    enableDetailedLogging: false,
+    socketTimeout: 5000,
+    routes: [{
+      name: 'backend-route',
+      match: { ports: 8581 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 9999  // Non-existent backend
+        }
+      }
+    }]
+  });
+  
+  // Create SmartProxy1 (upstream proxy)
+  const proxy1 = new SmartProxy({
+    ports: [8580],
+    enableDetailedLogging: false,
+    socketTimeout: 5000,
+    routes: [{
+      name: 'chain-route',
+      match: { ports: 8580 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 8581  // Forward to proxy2
+        }
+      }
+    }]
+  });
+  
+  // Start both proxies
+  await proxy2.start();
+  console.log('✓ SmartProxy2 started on port 8581');
+  
+  await proxy1.start();
+  console.log('✓ SmartProxy1 started on port 8580');
+  
+  // Helper to get connection counts
+  const getConnectionCounts = () => {
+    const conn1 = (proxy1 as any).connectionManager;
+    const conn2 = (proxy2 as any).connectionManager;
+    return {
+      proxy1: conn1 ? conn1.getConnectionCount() : 0,
+      proxy2: conn2 ? conn2.getConnectionCount() : 0
+    };
+  };
+  
+  const initialCounts = getConnectionCounts();
+  console.log(`\nInitial connection counts - Proxy1: ${initialCounts.proxy1}, Proxy2: ${initialCounts.proxy2}`);
+  
+  // Test 1: Single connection attempt
+  console.log('\n--- Test 1: Single connection through chain ---');
+  
+  await new Promise<void>((resolve) => {
+    const client = new net.Socket();
+    
+    client.on('error', (err) => {
+      console.log(`Client received error: ${err.code}`);
+      resolve();
+    });
+    
+    client.on('close', () => {
+      console.log('Client connection closed');
+      resolve();
+    });
+    
+    client.connect(8580, 'localhost', () => {
+      console.log('Client connected to Proxy1');
+      // Send data to trigger routing
+      client.write('GET / HTTP/1.1\r\nHost: test.com\r\n\r\n');
+    });
+    
+    // Timeout
+    setTimeout(() => {
+      if (!client.destroyed) {
+        client.destroy();
+      }
+      resolve();
+    }, 1000);
+  });
+  
+  // Check connections after single attempt
+  await new Promise(resolve => setTimeout(resolve, 500));
+  let counts = getConnectionCounts();
+  console.log(`After single connection - Proxy1: ${counts.proxy1}, Proxy2: ${counts.proxy2}`);
+  
+  // Test 2: Multiple simultaneous connections
+  console.log('\n--- Test 2: Multiple simultaneous connections ---');
+  
+  const promises = [];
+  for (let i = 0; i < 10; i++) {
+    promises.push(new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      
+      client.on('error', () => {
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(8580, 'localhost', () => {
+        // Send data
+        client.write(`GET /test${i} HTTP/1.1\r\nHost: test.com\r\n\r\n`);
+      });
+      
+      // Timeout
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+        resolve();
+      }, 500);
+    }));
+  }
+  
+  await Promise.all(promises);
+  console.log('✓ All simultaneous connections completed');
+  
+  // Check connections
+  counts = getConnectionCounts();
+  console.log(`After simultaneous connections - Proxy1: ${counts.proxy1}, Proxy2: ${counts.proxy2}`);
+  
+  // Test 3: Rapid serial connections (simulating retries)
+  console.log('\n--- Test 3: Rapid serial connections (retries) ---');
+  
+  for (let i = 0; i < 20; i++) {
+    await new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      
+      client.on('error', () => {
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(8580, 'localhost', () => {
+        client.write('GET / HTTP/1.1\r\nHost: test.com\r\n\r\n');
+        // Quick disconnect to simulate retry behavior
+        setTimeout(() => client.destroy(), 50);
+      });
+      
+      // Timeout
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+        resolve();
+      }, 200);
+    });
+    
+    if ((i + 1) % 5 === 0) {
+      counts = getConnectionCounts();
+      console.log(`After ${i + 1} retries - Proxy1: ${counts.proxy1}, Proxy2: ${counts.proxy2}`);
+    }
+    
+    // Small delay between retries
+    await new Promise(resolve => setTimeout(resolve, 50));
+  }
+  
+  // Test 4: Long-lived connection attempt
+  console.log('\n--- Test 4: Long-lived connection attempt ---');
+  
+  await new Promise<void>((resolve) => {
+    const client = new net.Socket();
+    
+    client.on('error', () => {
+      resolve();
+    });
+    
+    client.on('close', () => {
+      console.log('Long-lived client closed');
+      resolve();
+    });
+    
+    client.connect(8580, 'localhost', () => {
+      console.log('Long-lived client connected');
+      // Send data periodically
+      const interval = setInterval(() => {
+        if (!client.destroyed && client.writable) {
+          client.write('PING\r\n');
+        } else {
+          clearInterval(interval);
+        }
+      }, 100);
+      
+      // Close after 2 seconds
+      setTimeout(() => {
+        clearInterval(interval);
+        client.destroy();
+      }, 2000);
+    });
+    
+    // Timeout
+    setTimeout(() => {
+      if (!client.destroyed) {
+        client.destroy();
+      }
+      resolve();
+    }, 3000);
+  });
+  
+  // Final check
+  await new Promise(resolve => setTimeout(resolve, 1000));
+  
+  const finalCounts = getConnectionCounts();
+  console.log(`\nFinal connection counts - Proxy1: ${finalCounts.proxy1}, Proxy2: ${finalCounts.proxy2}`);
+  
+  // Monitor for a bit to see if connections are cleaned up
+  console.log('\nMonitoring connection cleanup...');
+  for (let i = 0; i < 3; i++) {
+    await new Promise(resolve => setTimeout(resolve, 500));
+    counts = getConnectionCounts();
+    console.log(`After ${(i + 1) * 0.5}s - Proxy1: ${counts.proxy1}, Proxy2: ${counts.proxy2}`);
+  }
+  
+  // Stop proxies
+  await proxy1.stop();
+  console.log('\n✓ SmartProxy1 stopped');
+  
+  await proxy2.stop();
+  console.log('✓ SmartProxy2 stopped');
+  
+  // Analysis
+  console.log('\n=== Analysis ===');
+  if (finalCounts.proxy1 > 0 || finalCounts.proxy2 > 0) {
+    console.log('❌ FAIL: Connections accumulated!');
+    console.log(`Proxy1 leaked ${finalCounts.proxy1} connections`);
+    console.log(`Proxy2 leaked ${finalCounts.proxy2} connections`);
+  } else {
+    console.log('✅ PASS: No connection accumulation detected');
+  }
+  
+  // Verify
+  expect(finalCounts.proxy1).toEqual(0);
+  expect(finalCounts.proxy2).toEqual(0);
+});
+
+tap.test('should handle proxy chain with HTTP traffic', async () => {
+  console.log('\n=== Testing Proxy Chain with HTTP Traffic ===');
+  
+  // Create SmartProxy2 with HTTP handling
+  const proxy2 = new SmartProxy({
+    ports: [8583],
+    useHttpProxy: [8583],  // Enable HTTP proxy handling
+    httpProxyPort: 8584,
+    enableDetailedLogging: false,
+    routes: [{
+      name: 'http-backend',
+      match: { ports: 8583 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 9999  // Non-existent backend
+        }
+      }
+    }]
+  });
+  
+  // Create SmartProxy1 with HTTP handling
+  const proxy1 = new SmartProxy({
+    ports: [8582],
+    useHttpProxy: [8582],  // Enable HTTP proxy handling
+    httpProxyPort: 8585,
+    enableDetailedLogging: false,
+    routes: [{
+      name: 'http-chain',
+      match: { ports: 8582 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 8583  // Forward to proxy2
+        }
+      }
+    }]
+  });
+  
+  await proxy2.start();
+  console.log('✓ SmartProxy2 (HTTP) started on port 8583');
+  
+  await proxy1.start();
+  console.log('✓ SmartProxy1 (HTTP) started on port 8582');
+  
+  // Helper to get connection counts
+  const getConnectionCounts = () => {
+    const conn1 = (proxy1 as any).connectionManager;
+    const conn2 = (proxy2 as any).connectionManager;
+    return {
+      proxy1: conn1 ? conn1.getConnectionCount() : 0,
+      proxy2: conn2 ? conn2.getConnectionCount() : 0
+    };
+  };
+  
+  console.log('\nSending HTTP requests through chain...');
+  
+  // Make HTTP requests
+  for (let i = 0; i < 5; i++) {
+    await new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      let responseData = '';
+      
+      client.on('data', (data) => {
+        responseData += data.toString();
+        // Check if we got a complete HTTP response
+        if (responseData.includes('\r\n\r\n')) {
+          console.log(`Response ${i + 1}: ${responseData.split('\r\n')[0]}`);
+          client.destroy();
+        }
+      });
+      
+      client.on('error', () => {
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(8582, 'localhost', () => {
+        client.write(`GET /test${i} HTTP/1.1\r\nHost: test.com\r\nConnection: close\r\n\r\n`);
+      });
+      
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+        resolve();
+      }, 1000);
+    });
+    
+    await new Promise(resolve => setTimeout(resolve, 100));
+  }
+  
+  await new Promise(resolve => setTimeout(resolve, 1000));
+  
+  const finalCounts = getConnectionCounts();
+  console.log(`\nFinal HTTP proxy counts - Proxy1: ${finalCounts.proxy1}, Proxy2: ${finalCounts.proxy2}`);
+  
+  await proxy1.stop();
+  await proxy2.stop();
+  
+  expect(finalCounts.proxy1).toEqual(0);
+  expect(finalCounts.proxy2).toEqual(0);
+});
+
+tap.start();

test/test.rapid-retry-cleanup.node.ts

@@ -0,0 +1,201 @@
+import { tap, expect } from '@git.zone/tstest/tapbundle';
+import * as net from 'net';
+import * as plugins from '../ts/plugins.js';
+
+// Import SmartProxy and configurations
+import { SmartProxy } from '../ts/index.js';
+
+tap.test('should handle rapid connection retries without leaking connections', async () => {
+  console.log('\n=== Testing Rapid Connection Retry Cleanup ===');
+  
+  // Create a SmartProxy instance
+  const proxy = new SmartProxy({
+    ports: [8550],
+    enableDetailedLogging: false,
+    maxConnectionLifetime: 10000,
+    socketTimeout: 5000,
+    routes: [{
+      name: 'test-route',
+      match: { ports: 8550 },
+      action: {
+        type: 'forward',
+        target: {
+          host: 'localhost',
+          port: 9999  // Non-existent port to force connection failures
+        }
+      }
+    }]
+  });
+  
+  // Start the proxy
+  await proxy.start();
+  console.log('✓ Proxy started on port 8550');
+  
+  // Helper to get active connection count
+  const getActiveConnections = () => {
+    const connectionManager = (proxy as any).connectionManager;
+    return connectionManager ? connectionManager.getConnectionCount() : 0;
+  };
+  
+  // Track connection counts
+  const connectionCounts: number[] = [];
+  const initialCount = getActiveConnections();
+  console.log(`Initial connection count: ${initialCount}`);
+  
+  // Simulate rapid retries
+  const retryCount = 20;
+  const retryDelay = 50; // 50ms between retries
+  let successfulConnections = 0;
+  let failedConnections = 0;
+  
+  console.log(`\nSimulating ${retryCount} rapid connection attempts...`);
+  
+  for (let i = 0; i < retryCount; i++) {
+    await new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      
+      client.on('error', () => {
+        failedConnections++;
+        client.destroy();
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(8550, 'localhost', () => {
+        // Send some data to trigger routing
+        client.write('GET / HTTP/1.1\r\nHost: test.com\r\n\r\n');
+        successfulConnections++;
+      });
+      
+      // Force close after a short time
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+      }, 100);
+    });
+    
+    // Small delay between retries
+    await new Promise(resolve => setTimeout(resolve, retryDelay));
+    
+    // Check connection count after each attempt
+    const currentCount = getActiveConnections();
+    connectionCounts.push(currentCount);
+    
+    if ((i + 1) % 5 === 0) {
+      console.log(`After ${i + 1} attempts: ${currentCount} active connections`);
+    }
+  }
+  
+  console.log(`\nConnection attempts complete:`);
+  console.log(`- Successful: ${successfulConnections}`);
+  console.log(`- Failed: ${failedConnections}`);
+  
+  // Wait a bit for any pending cleanups
+  console.log('\nWaiting for cleanup...');
+  await new Promise(resolve => setTimeout(resolve, 1000));
+  
+  // Check final connection count
+  const finalCount = getActiveConnections();
+  console.log(`\nFinal connection count: ${finalCount}`);
+  
+  // Analyze connection count trend
+  const maxCount = Math.max(...connectionCounts);
+  const avgCount = connectionCounts.reduce((a, b) => a + b, 0) / connectionCounts.length;
+  
+  console.log(`\nConnection count statistics:`);
+  console.log(`- Maximum: ${maxCount}`);
+  console.log(`- Average: ${avgCount.toFixed(2)}`);
+  console.log(`- Initial: ${initialCount}`);
+  console.log(`- Final: ${finalCount}`);
+  
+  // Stop the proxy
+  await proxy.stop();
+  console.log('\n✓ Proxy stopped');
+  
+  // Verify results
+  expect(finalCount).toEqual(initialCount);
+  expect(maxCount).toBeLessThan(10); // Should not accumulate many connections
+  
+  console.log('\n✅ PASS: Connection cleanup working correctly under rapid retries!');
+});
+
+tap.test('should handle routing failures without leaking connections', async () => {
+  console.log('\n=== Testing Routing Failure Cleanup ===');
+  
+  // Create a SmartProxy instance with no routes
+  const proxy = new SmartProxy({
+    ports: [8551],
+    enableDetailedLogging: false,
+    maxConnectionLifetime: 10000,
+    socketTimeout: 5000,
+    routes: [] // No routes - all connections will fail routing
+  });
+  
+  // Start the proxy
+  await proxy.start();
+  console.log('✓ Proxy started on port 8551 with no routes');
+  
+  // Helper to get active connection count
+  const getActiveConnections = () => {
+    const connectionManager = (proxy as any).connectionManager;
+    return connectionManager ? connectionManager.getConnectionCount() : 0;
+  };
+  
+  const initialCount = getActiveConnections();
+  console.log(`Initial connection count: ${initialCount}`);
+  
+  // Create multiple connections that will fail routing
+  const connectionPromises = [];
+  for (let i = 0; i < 10; i++) {
+    connectionPromises.push(new Promise<void>((resolve) => {
+      const client = new net.Socket();
+      
+      client.on('error', () => {
+        client.destroy();
+        resolve();
+      });
+      
+      client.on('close', () => {
+        resolve();
+      });
+      
+      client.connect(8551, 'localhost', () => {
+        // Send data to trigger routing (which will fail)
+        client.write('GET / HTTP/1.1\r\nHost: test.com\r\n\r\n');
+      });
+      
+      // Force close after a short time
+      setTimeout(() => {
+        if (!client.destroyed) {
+          client.destroy();
+        }
+        resolve();
+      }, 500);
+    }));
+  }
+  
+  // Wait for all connections to complete
+  await Promise.all(connectionPromises);
+  console.log('✓ All connection attempts completed');
+  
+  // Wait for cleanup
+  await new Promise(resolve => setTimeout(resolve, 500));
+  
+  const finalCount = getActiveConnections();
+  console.log(`Final connection count: ${finalCount}`);
+  
+  // Stop the proxy
+  await proxy.stop();
+  console.log('✓ Proxy stopped');
+  
+  // Verify no connections leaked
+  expect(finalCount).toEqual(initialCount);
+  
+  console.log('\n✅ PASS: Routing failures cleaned up correctly!');
+});
+
+tap.start();

ts/core/utils/enhanced-connection-pool.ts

@@ -403,7 +403,12 @@ export class EnhancedConnectionPool<T> extends LifecycleComponent {
     const startTime = Date.now();
     
     while (this.activeConnections.size > 0 && Date.now() - startTime < timeout) {
-      await new Promise(resolve => setTimeout(resolve, 100));
+      await new Promise(resolve => {
+        const timer = setTimeout(resolve, 100);
+        if (typeof timer.unref === 'function') {
+          timer.unref();
+        }
+      });
     }
     
     // Destroy all connections

ts/core/utils/lifecycle-component.ts

@@ -9,6 +9,7 @@ export abstract class LifecycleComponent {
     target: any; 
     event: string; 
     handler: Function;
+    actualHandler?: Function; // The actual handler registered (may be wrapped)
     once?: boolean;
   }> = [];
   private childComponents: Set<LifecycleComponent> = new Set();
@@ -21,7 +22,11 @@ export abstract class LifecycleComponent {
   protected setTimeout(handler: Function, timeout: number): NodeJS.Timeout {
     if (this.isShuttingDown) {
       // Return a dummy timer if shutting down
-      return setTimeout(() => {}, 0);
+      const dummyTimer = setTimeout(() => {}, 0);
+      if (typeof dummyTimer.unref === 'function') {
+        dummyTimer.unref();
+      }
+      return dummyTimer;
     }
 
     const wrappedHandler = () => {
@@ -33,6 +38,12 @@ export abstract class LifecycleComponent {
 
     const timer = setTimeout(wrappedHandler, timeout);
     this.timers.add(timer);
+    
+    // Allow process to exit even with timer
+    if (typeof timer.unref === 'function') {
+      timer.unref();
+    }
+    
     return timer;
   }
 
@@ -42,7 +53,12 @@ export abstract class LifecycleComponent {
   protected setInterval(handler: Function, interval: number): NodeJS.Timeout {
     if (this.isShuttingDown) {
       // Return a dummy timer if shutting down
-      return setInterval(() => {}, interval);
+      const dummyTimer = setInterval(() => {}, interval);
+      if (typeof dummyTimer.unref === 'function') {
+        dummyTimer.unref();
+      }
+      clearInterval(dummyTimer); // Clear immediately since we don't need it
+      return dummyTimer;
     }
 
     const wrappedHandler = () => {
@@ -121,11 +137,12 @@ export abstract class LifecycleComponent {
       throw new Error('Target must support on() or addEventListener()');
     }
 
-    // Store the original handler in our tracking (not the wrapped one)
+    // Store both the original handler and the actual handler registered
     this.listeners.push({ 
       target, 
       event, 
       handler,
+      actualHandler, // The handler that was actually registered (may be wrapped)
       once: options?.once 
     });
   }
@@ -208,12 +225,15 @@ export abstract class LifecycleComponent {
     this.intervals.clear();
 
     // Remove all event listeners
-    for (const { target, event, handler } of this.listeners) {
+    for (const { target, event, handler, actualHandler } of this.listeners) {
+      // Use actualHandler if available (for wrapped handlers), otherwise use the original handler
+      const handlerToRemove = actualHandler || handler;
+      
       // All listeners need to be removed, including 'once' listeners that might not have fired
       if (typeof target.removeListener === 'function') {
-        target.removeListener(event, handler);
+        target.removeListener(event, handlerToRemove);
       } else if (typeof target.removeEventListener === 'function') {
-        target.removeEventListener(event, handler);
+        target.removeEventListener(event, handlerToRemove);
       }
     }
     this.listeners = [];

ts/core/utils/socket-utils.ts

@@ -1,27 +1,70 @@
 import * as plugins from '../../plugins.js';
 
+export interface CleanupOptions {
+  immediate?: boolean;      // Force immediate destruction
+  allowDrain?: boolean;     // Allow write buffer to drain
+  gracePeriod?: number;     // Ms to wait before force close
+}
+
+export interface SafeSocketOptions {
+  port: number;
+  host: string;
+  onError?: (error: Error) => void;
+  onConnect?: () => void;
+  timeout?: number;
+}
+
 /**
  * Safely cleanup a socket by removing all listeners and destroying it
  * @param socket The socket to cleanup
  * @param socketName Optional name for logging
+ * @param options Cleanup options
  */
-export function cleanupSocket(socket: plugins.net.Socket | plugins.tls.TLSSocket | null, socketName?: string): void {
-  if (!socket) return;
+export function cleanupSocket(
+  socket: plugins.net.Socket | plugins.tls.TLSSocket | null, 
+  socketName?: string,
+  options: CleanupOptions = {}
+): Promise<void> {
+  if (!socket || socket.destroyed) return Promise.resolve();
   
-  try {
-    // Remove all event listeners
-    socket.removeAllListeners();
+  return new Promise<void>((resolve) => {
+    const cleanup = () => {
+      try {
+        // Remove all event listeners
+        socket.removeAllListeners();
+        
+        // Destroy if not already destroyed
+        if (!socket.destroyed) {
+          socket.destroy();
+        }
+      } catch (err) {
+        console.error(`Error cleaning up socket${socketName ? ` (${socketName})` : ''}: ${err}`);
+      }
+      resolve();
+    };
     
-    // Unpipe any streams
-    socket.unpipe();
-    
-    // Destroy if not already destroyed
-    if (!socket.destroyed) {
-      socket.destroy();
+    if (options.immediate) {
+      // Immediate cleanup (old behavior)
+      socket.unpipe();
+      cleanup();
+    } else if (options.allowDrain && socket.writable) {
+      // Allow pending writes to complete
+      socket.end(() => cleanup());
+      
+      // Force cleanup after grace period
+      if (options.gracePeriod) {
+        setTimeout(() => {
+          if (!socket.destroyed) {
+            cleanup();
+          }
+        }, options.gracePeriod);
+      }
+    } else {
+      // Default: immediate cleanup
+      socket.unpipe();
+      cleanup();
     }
-  } catch (err) {
-    console.error(`Error cleaning up socket${socketName ? ` (${socketName})` : ''}: ${err}`);
-  }
+  });
 }
 
 /**
@@ -30,6 +73,7 @@ export function cleanupSocket(socket: plugins.net.Socket | plugins.tls.TLSSocket
  * @param serverSocket The server socket (optional)
  * @param onCleanup Optional callback when cleanup is done
  * @returns A cleanup function that can be called multiple times safely
+ * @deprecated Use createIndependentSocketHandlers for better half-open support
  */
 export function createSocketCleanupHandler(
   clientSocket: plugins.net.Socket | plugins.tls.TLSSocket,
@@ -42,10 +86,10 @@ export function createSocketCleanupHandler(
     if (cleanedUp) return;
     cleanedUp = true;
     
-    // Cleanup both sockets
-    cleanupSocket(clientSocket, 'client');
+    // Cleanup both sockets (old behavior - too aggressive)
+    cleanupSocket(clientSocket, 'client', { immediate: true });
     if (serverSocket) {
-      cleanupSocket(serverSocket, 'server');
+      cleanupSocket(serverSocket, 'server', { immediate: true });
     }
     
     // Call cleanup callback if provided
@@ -55,15 +99,90 @@ export function createSocketCleanupHandler(
   };
 }
 
+/**
+ * Create independent cleanup handlers for paired sockets that support half-open connections
+ * @param clientSocket The client socket
+ * @param serverSocket The server socket
+ * @param onBothClosed Callback when both sockets are closed
+ * @returns Independent cleanup functions for each socket
+ */
+export function createIndependentSocketHandlers(
+  clientSocket: plugins.net.Socket | plugins.tls.TLSSocket,
+  serverSocket: plugins.net.Socket | plugins.tls.TLSSocket,
+  onBothClosed: (reason: string) => void,
+  options: { enableHalfOpen?: boolean } = {}
+): { cleanupClient: (reason: string) => Promise<void>, cleanupServer: (reason: string) => Promise<void> } {
+  let clientClosed = false;
+  let serverClosed = false;
+  let clientReason = '';
+  let serverReason = '';
+  
+  const checkBothClosed = () => {
+    if (clientClosed && serverClosed) {
+      onBothClosed(`client: ${clientReason}, server: ${serverReason}`);
+    }
+  };
+  
+  const cleanupClient = async (reason: string) => {
+    if (clientClosed) return;
+    clientClosed = true;
+    clientReason = reason;
+    
+    // Default behavior: close both sockets when one closes (required for proxy chains)
+    if (!serverClosed && !options.enableHalfOpen) {
+      serverSocket.destroy();
+    }
+    
+    // Half-open support (opt-in only)
+    if (!serverClosed && serverSocket.writable && options.enableHalfOpen) {
+      // Half-close: stop reading from client, let server finish
+      clientSocket.pause();
+      clientSocket.unpipe(serverSocket);
+      await cleanupSocket(clientSocket, 'client', { allowDrain: true, gracePeriod: 5000 });
+    } else {
+      await cleanupSocket(clientSocket, 'client', { immediate: true });
+    }
+    
+    checkBothClosed();
+  };
+  
+  const cleanupServer = async (reason: string) => {
+    if (serverClosed) return;
+    serverClosed = true;
+    serverReason = reason;
+    
+    // Default behavior: close both sockets when one closes (required for proxy chains)
+    if (!clientClosed && !options.enableHalfOpen) {
+      clientSocket.destroy();
+    }
+    
+    // Half-open support (opt-in only)
+    if (!clientClosed && clientSocket.writable && options.enableHalfOpen) {
+      // Half-close: stop reading from server, let client finish
+      serverSocket.pause();
+      serverSocket.unpipe(clientSocket);
+      await cleanupSocket(serverSocket, 'server', { allowDrain: true, gracePeriod: 5000 });
+    } else {
+      await cleanupSocket(serverSocket, 'server', { immediate: true });
+    }
+    
+    checkBothClosed();
+  };
+  
+  return { cleanupClient, cleanupServer };
+}
+
 /**
  * Setup socket error and close handlers with proper cleanup
  * @param socket The socket to setup handlers for
  * @param handleClose The cleanup function to call
+ * @param handleTimeout Optional custom timeout handler
  * @param errorPrefix Optional prefix for error messages
  */
 export function setupSocketHandlers(
   socket: plugins.net.Socket | plugins.tls.TLSSocket,
   handleClose: (reason: string) => void,
+  handleTimeout?: (socket: plugins.net.Socket | plugins.tls.TLSSocket) => void,
   errorPrefix?: string
 ): void {
   socket.on('error', (error) => {
@@ -77,11 +196,88 @@ export function setupSocketHandlers(
   });
   
   socket.on('timeout', () => {
-    const prefix = errorPrefix || 'socket';
-    handleClose(`${prefix}_timeout`);
+    if (handleTimeout) {
+      handleTimeout(socket);  // Custom timeout handling
+    } else {
+      // Default: just log, don't close
+      console.warn(`Socket timeout: ${errorPrefix || 'socket'}`);
+    }
   });
 }
 
+/**
+ * Setup bidirectional data forwarding between two sockets with proper cleanup
+ * @param clientSocket The client/incoming socket
+ * @param serverSocket The server/outgoing socket
+ * @param handlers Object containing optional handlers for data and cleanup
+ * @returns Cleanup functions for both sockets
+ */
+export function setupBidirectionalForwarding(
+  clientSocket: plugins.net.Socket | plugins.tls.TLSSocket,
+  serverSocket: plugins.net.Socket | plugins.tls.TLSSocket,
+  handlers: {
+    onClientData?: (chunk: Buffer) => void;
+    onServerData?: (chunk: Buffer) => void;
+    onCleanup: (reason: string) => void;
+    enableHalfOpen?: boolean;
+  }
+): { cleanupClient: (reason: string) => Promise<void>, cleanupServer: (reason: string) => Promise<void> } {
+  // Set up cleanup handlers
+  const { cleanupClient, cleanupServer } = createIndependentSocketHandlers(
+    clientSocket,
+    serverSocket,
+    handlers.onCleanup,
+    { enableHalfOpen: handlers.enableHalfOpen }
+  );
+  
+  // Set up error and close handlers
+  setupSocketHandlers(clientSocket, cleanupClient, undefined, 'client');
+  setupSocketHandlers(serverSocket, cleanupServer, undefined, 'server');
+  
+  // Set up data forwarding with backpressure handling
+  clientSocket.on('data', (chunk: Buffer) => {
+    if (handlers.onClientData) {
+      handlers.onClientData(chunk);
+    }
+    
+    if (serverSocket.writable) {
+      const flushed = serverSocket.write(chunk);
+      
+      // Handle backpressure
+      if (!flushed) {
+        clientSocket.pause();
+        serverSocket.once('drain', () => {
+          if (!clientSocket.destroyed) {
+            clientSocket.resume();
+          }
+        });
+      }
+    }
+  });
+  
+  serverSocket.on('data', (chunk: Buffer) => {
+    if (handlers.onServerData) {
+      handlers.onServerData(chunk);
+    }
+    
+    if (clientSocket.writable) {
+      const flushed = clientSocket.write(chunk);
+      
+      // Handle backpressure
+      if (!flushed) {
+        serverSocket.pause();
+        clientSocket.once('drain', () => {
+          if (!serverSocket.destroyed) {
+            serverSocket.resume();
+          }
+        });
+      }
+    }
+  });
+  
+  return { cleanupClient, cleanupServer };
+}
+
 /**
  * Pipe two sockets together with proper cleanup on either end
  * @param socket1 First socket
@@ -93,4 +289,39 @@ export function pipeSockets(
 ): void {
   socket1.pipe(socket2);
   socket2.pipe(socket1);
+}
+
+/**
+ * Create a socket with immediate error handling to prevent crashes
+ * @param options Socket creation options
+ * @returns The created socket
+ */
+export function createSocketWithErrorHandler(options: SafeSocketOptions): plugins.net.Socket {
+  const { port, host, onError, onConnect, timeout } = options;
+  
+  // Create socket with immediate error handler attachment
+  const socket = new plugins.net.Socket();
+  
+  // Attach error handler BEFORE connecting to catch immediate errors
+  socket.on('error', (error) => {
+    console.error(`Socket connection error to ${host}:${port}: ${error.message}`);
+    if (onError) {
+      onError(error);
+    }
+  });
+  
+  // Attach connect handler if provided
+  if (onConnect) {
+    socket.on('connect', onConnect);
+  }
+  
+  // Set timeout if provided
+  if (timeout) {
+    socket.setTimeout(timeout);
+  }
+  
+  // Now attempt to connect - any immediate errors will be caught
+  socket.connect(port, host);
+  
+  return socket;
 }

ts/forwarding/handlers/http-handler.ts

@@ -49,7 +49,12 @@ export class HttpForwardingHandler extends ForwardingHandler {
       });
     };
     
-    setupSocketHandlers(socket, handleClose, 'http');
+    // Use custom timeout handler that doesn't close the socket
+    setupSocketHandlers(socket, handleClose, () => {
+      // For HTTP, we can be more aggressive with timeouts since connections are shorter
+      // But still don't close immediately - let the connection finish naturally
+      console.warn(`HTTP socket timeout from ${remoteAddress}`);
+    }, 'http');
     
     socket.on('error', (error) => {
       this.emit(ForwardingHandlerEvents.ERROR, {

ts/forwarding/handlers/https-passthrough-handler.ts

@@ -2,7 +2,7 @@ import * as plugins from '../../plugins.js';
 import { ForwardingHandler } from './base-handler.js';
 import type { IForwardConfig } from '../config/forwarding-types.js';
 import { ForwardingHandlerEvents } from '../config/forwarding-types.js';
-import { createSocketCleanupHandler, setupSocketHandlers, pipeSockets } from '../../core/utils/socket-utils.js';
+import { createIndependentSocketHandlers, setupSocketHandlers, createSocketWithErrorHandler } from '../../core/utils/socket-utils.js';
 
 /**
  * Handler for HTTPS passthrough (SNI forwarding without termination)
@@ -48,79 +48,122 @@ export class HttpsPassthroughHandler extends ForwardingHandler {
       target: `${target.host}:${target.port}`
     });
     
-    // Create a connection to the target server
-    const serverSocket = plugins.net.connect(target.port, target.host);
-    
     // Track data transfer for logging
     let bytesSent = 0;
     let bytesReceived = 0;
+    let serverSocket: plugins.net.Socket | null = null;
+    let cleanupClient: ((reason: string) => Promise<void>) | null = null;
+    let cleanupServer: ((reason: string) => Promise<void>) | null = null;
     
-    // Create cleanup handler with our utility
-    const handleClose = createSocketCleanupHandler(clientSocket, serverSocket, (reason) => {
-      this.emit(ForwardingHandlerEvents.DISCONNECTED, {
-        remoteAddress,
-        bytesSent,
-        bytesReceived,
-        reason
-      });
-    });
-    
-    // Setup error and close handlers for both sockets
-    setupSocketHandlers(serverSocket, handleClose, 'server');
-    setupSocketHandlers(clientSocket, handleClose, 'client');
-    
-    // Forward data from client to server
-    clientSocket.on('data', (data) => {
-      bytesSent += data.length;
-      
-      // Check if server socket is writable
-      if (serverSocket.writable) {
-        const flushed = serverSocket.write(data);
+    // Create a connection to the target server with immediate error handling
+    serverSocket = createSocketWithErrorHandler({
+      port: target.port,
+      host: target.host,
+      onError: async (error) => {
+        // Server connection failed - clean up client socket immediately
+        this.emit(ForwardingHandlerEvents.ERROR, {
+          error: error.message,
+          code: (error as any).code || 'UNKNOWN',
+          remoteAddress,
+          target: `${target.host}:${target.port}`
+        });
         
-        // Handle backpressure
-        if (!flushed) {
-          clientSocket.pause();
-          serverSocket.once('drain', () => {
-            clientSocket.resume();
-          });
+        // Clean up the client socket since we can't forward
+        if (!clientSocket.destroyed) {
+          clientSocket.destroy();
         }
-      }
-      
-      this.emit(ForwardingHandlerEvents.DATA_FORWARDED, {
-        direction: 'outbound',
-        bytes: data.length,
-        total: bytesSent
-      });
-    });
-    
-    // Forward data from server to client
-    serverSocket.on('data', (data) => {
-      bytesReceived += data.length;
-      
-      // Check if client socket is writable
-      if (clientSocket.writable) {
-        const flushed = clientSocket.write(data);
         
-        // Handle backpressure
-        if (!flushed) {
-          serverSocket.pause();
-          clientSocket.once('drain', () => {
-            serverSocket.resume();
+        this.emit(ForwardingHandlerEvents.DISCONNECTED, {
+          remoteAddress,
+          bytesSent: 0,
+          bytesReceived: 0,
+          reason: `server_connection_failed: ${error.message}`
+        });
+      },
+      onConnect: () => {
+        // Connection successful - set up forwarding handlers
+        const handlers = createIndependentSocketHandlers(
+          clientSocket,
+          serverSocket!,
+          (reason) => {
+            this.emit(ForwardingHandlerEvents.DISCONNECTED, {
+              remoteAddress,
+              bytesSent,
+              bytesReceived,
+              reason
+            });
+          }
+        );
+        
+        cleanupClient = handlers.cleanupClient;
+        cleanupServer = handlers.cleanupServer;
+        
+        // Setup handlers with custom timeout handling that doesn't close connections
+        const timeout = this.getTimeout();
+        
+        setupSocketHandlers(clientSocket, cleanupClient, (socket) => {
+          // Just reset timeout, don't close
+          socket.setTimeout(timeout);
+        }, 'client');
+        
+        setupSocketHandlers(serverSocket!, cleanupServer, (socket) => {
+          // Just reset timeout, don't close  
+          socket.setTimeout(timeout);
+        }, 'server');
+        
+        // Forward data from client to server
+        clientSocket.on('data', (data) => {
+          bytesSent += data.length;
+          
+          // Check if server socket is writable
+          if (serverSocket && serverSocket.writable) {
+            const flushed = serverSocket.write(data);
+            
+            // Handle backpressure
+            if (!flushed) {
+              clientSocket.pause();
+              serverSocket.once('drain', () => {
+                clientSocket.resume();
+              });
+            }
+          }
+          
+          this.emit(ForwardingHandlerEvents.DATA_FORWARDED, {
+            direction: 'outbound',
+            bytes: data.length,
+            total: bytesSent
           });
-        }
+        });
+        
+        // Forward data from server to client
+        serverSocket!.on('data', (data) => {
+          bytesReceived += data.length;
+          
+          // Check if client socket is writable
+          if (clientSocket.writable) {
+            const flushed = clientSocket.write(data);
+            
+            // Handle backpressure
+            if (!flushed) {
+              serverSocket!.pause();
+              clientSocket.once('drain', () => {
+                serverSocket!.resume();
+              });
+            }
+          }
+          
+          this.emit(ForwardingHandlerEvents.DATA_FORWARDED, {
+            direction: 'inbound',
+            bytes: data.length,
+            total: bytesReceived
+          });
+        });
+        
+        // Set initial timeouts - they will be reset on each timeout event  
+        clientSocket.setTimeout(timeout);
+        serverSocket!.setTimeout(timeout);
       }
-      
-      this.emit(ForwardingHandlerEvents.DATA_FORWARDED, {
-        direction: 'inbound',
-        bytes: data.length,
-        total: bytesReceived
-      });
     });
-    
-    // Set timeouts
-    const timeout = this.getTimeout();
-    clientSocket.setTimeout(timeout);
-    serverSocket.setTimeout(timeout);
   }
   
   /**
@@ -128,7 +171,7 @@ export class HttpsPassthroughHandler extends ForwardingHandler {
    * @param req The HTTP request
    * @param res The HTTP response
    */
-  public handleHttpRequest(req: plugins.http.IncomingMessage, res: plugins.http.ServerResponse): void {
+  public handleHttpRequest(_req: plugins.http.IncomingMessage, res: plugins.http.ServerResponse): void {
     // HTTPS passthrough doesn't support HTTP requests
     res.writeHead(404, { 'Content-Type': 'text/plain' });
     res.end('HTTP not supported for this domain');

ts/forwarding/handlers/https-terminate-to-http-handler.ts

@@ -2,7 +2,7 @@ import * as plugins from '../../plugins.js';
 import { ForwardingHandler } from './base-handler.js';
 import type { IForwardConfig } from '../config/forwarding-types.js';
 import { ForwardingHandlerEvents } from '../config/forwarding-types.js';
-import { createSocketCleanupHandler, setupSocketHandlers } from '../../core/utils/socket-utils.js';
+import { createSocketCleanupHandler, setupSocketHandlers, createSocketWithErrorHandler } from '../../core/utils/socket-utils.js';
 
 /**
  * Handler for HTTPS termination with HTTP backend
@@ -112,7 +112,7 @@ export class HttpsTerminateToHttpHandler extends ForwardingHandler {
     });
     
     // Set up error handling with our cleanup utility
-    setupSocketHandlers(tlsSocket, handleClose, 'tls');
+    setupSocketHandlers(tlsSocket, handleClose, undefined, 'tls');
     
     // Set timeout
     const timeout = this.getTimeout();
@@ -141,19 +141,41 @@ export class HttpsTerminateToHttpHandler extends ForwardingHandler {
       if (dataBuffer.includes(Buffer.from('\r\n\r\n')) && !connectionEstablished) {
         const target = this.getTargetFromConfig();
         
-        // Create backend connection
-        backendSocket = plugins.net.connect(target.port, target.host, () => {
-          connectionEstablished = true;
-          
-          // Send buffered data
-          if (dataBuffer.length > 0) {
-            backendSocket!.write(dataBuffer);
-            dataBuffer = Buffer.alloc(0);
+        // Create backend connection with immediate error handling
+        backendSocket = createSocketWithErrorHandler({
+          port: target.port,
+          host: target.host,
+          onError: (error) => {
+            this.emit(ForwardingHandlerEvents.ERROR, {
+              error: error.message,
+              code: (error as any).code || 'UNKNOWN',
+              remoteAddress,
+              target: `${target.host}:${target.port}`
+            });
+            
+            // Clean up the TLS socket since we can't forward
+            if (!tlsSocket.destroyed) {
+              tlsSocket.destroy();
+            }
+            
+            this.emit(ForwardingHandlerEvents.DISCONNECTED, {
+              remoteAddress,
+              reason: `backend_connection_failed: ${error.message}`
+            });
+          },
+          onConnect: () => {
+            connectionEstablished = true;
+            
+            // Send buffered data
+            if (dataBuffer.length > 0) {
+              backendSocket!.write(dataBuffer);
+              dataBuffer = Buffer.alloc(0);
+            }
+            
+            // Set up bidirectional data flow
+            tlsSocket.pipe(backendSocket!);
+            backendSocket!.pipe(tlsSocket);
           }
-          
-          // Set up bidirectional data flow
-          tlsSocket.pipe(backendSocket!);
-          backendSocket!.pipe(tlsSocket);
         });
         
         // Update the cleanup handler with the backend socket
@@ -167,7 +189,7 @@ export class HttpsTerminateToHttpHandler extends ForwardingHandler {
         });
         
         // Set up handlers for backend socket
-        setupSocketHandlers(backendSocket, newHandleClose, 'backend');
+        setupSocketHandlers(backendSocket, newHandleClose, undefined, 'backend');
         
         backendSocket.on('error', (error) => {
           this.emit(ForwardingHandlerEvents.ERROR, {

ts/forwarding/handlers/https-terminate-to-https-handler.ts

@@ -2,7 +2,7 @@ import * as plugins from '../../plugins.js';
 import { ForwardingHandler } from './base-handler.js';
 import type { IForwardConfig } from '../config/forwarding-types.js';
 import { ForwardingHandlerEvents } from '../config/forwarding-types.js';
-import { createSocketCleanupHandler, setupSocketHandlers } from '../../core/utils/socket-utils.js';
+import { createSocketCleanupHandler, setupSocketHandlers, createSocketWithErrorHandler } from '../../core/utils/socket-utils.js';
 
 /**
  * Handler for HTTPS termination with HTTPS backend
@@ -106,7 +106,7 @@ export class HttpsTerminateToHttpsHandler extends ForwardingHandler {
     });
     
     // Set up error handling with our cleanup utility
-    setupSocketHandlers(tlsSocket, handleClose, 'tls');
+    setupSocketHandlers(tlsSocket, handleClose, undefined, 'tls');
     
     // Set timeout
     const timeout = this.getTimeout();
@@ -151,7 +151,7 @@ export class HttpsTerminateToHttpsHandler extends ForwardingHandler {
       });
       
       // Set up handlers for backend socket
-      setupSocketHandlers(backendSocket, newHandleClose, 'backend');
+      setupSocketHandlers(backendSocket, newHandleClose, undefined, 'backend');
       
       backendSocket.on('error', (error) => {
         this.emit(ForwardingHandlerEvents.ERROR, {

ts/proxies/http-proxy/connection-pool.ts

@@ -134,7 +134,7 @@ export class ConnectionPool {
         if ((connection.isIdle && now - connection.lastUsed > idleTimeout) ||
             connections.length > (this.options.connectionPoolSize || 50)) {
           
-          cleanupSocket(connection.socket, `pool-${host}-idle`);
+          cleanupSocket(connection.socket, `pool-${host}-idle`, { immediate: true }).catch(() => {});
           
           connections.shift(); // Remove from pool
           removed++;
@@ -164,7 +164,7 @@ export class ConnectionPool {
       this.logger.debug(`Closing ${connections.length} connections to ${host}`);
       
       for (const connection of connections) {
-        cleanupSocket(connection.socket, `pool-${host}-close`);
+        cleanupSocket(connection.socket, `pool-${host}-close`, { immediate: true }).catch(() => {});
       }
     }
     

ts/proxies/http-proxy/http-proxy.ts

@@ -520,9 +520,10 @@ export class HttpProxy implements IMetricsTracker {
     this.webSocketHandler.shutdown();
     
     // Close all tracked sockets
-    for (const socket of this.socketMap.getArray()) {
-      cleanupSocket(socket, 'http-proxy-stop');
-    }
+    const socketCleanupPromises = this.socketMap.getArray().map(socket => 
+      cleanupSocket(socket, 'http-proxy-stop', { immediate: true })
+    );
+    await Promise.all(socketCleanupPromises);
     
     // Close all connection pool connections
     this.connectionPool.closeAllConnections();

ts/proxies/smart-proxy/connection-manager.ts

@@ -278,12 +278,37 @@ export class ConnectionManager extends LifecycleComponent {
         }
       }
 
-      // Handle socket cleanup without delay
-      cleanupSocket(record.incoming, `${record.id}-incoming`);
+      // Handle socket cleanup - check if sockets are still active
+      const cleanupPromises: Promise<void>[] = [];
+      
+      if (record.incoming) {
+        if (!record.incoming.writable || record.incoming.destroyed) {
+          // Socket is not active, clean up immediately
+          cleanupPromises.push(cleanupSocket(record.incoming, `${record.id}-incoming`, { immediate: true }));
+        } else {
+          // Socket is still active, allow graceful cleanup
+          cleanupPromises.push(cleanupSocket(record.incoming, `${record.id}-incoming`, { allowDrain: true, gracePeriod: 5000 }));
+        }
+      }
       
       if (record.outgoing) {
-        cleanupSocket(record.outgoing, `${record.id}-outgoing`);
+        if (!record.outgoing.writable || record.outgoing.destroyed) {
+          // Socket is not active, clean up immediately
+          cleanupPromises.push(cleanupSocket(record.outgoing, `${record.id}-outgoing`, { immediate: true }));
+        } else {
+          // Socket is still active, allow graceful cleanup
+          cleanupPromises.push(cleanupSocket(record.outgoing, `${record.id}-outgoing`, { allowDrain: true, gracePeriod: 5000 }));
+        }
       }
+      
+      // Wait for cleanup to complete
+      Promise.all(cleanupPromises).catch(err => {
+        logger.log('error', `Error during socket cleanup: ${err}`, {
+          connectionId: record.id,
+          error: err,
+          component: 'connection-manager'
+        });
+      });
 
       // Clear pendingData to avoid memory leaks
       record.pendingData = [];
@@ -484,19 +509,24 @@ export class ConnectionManager extends LifecycleComponent {
       }
       
       // Parity check: if outgoing socket closed and incoming remains active
+      // Increased from 2 minutes to 30 minutes for long-lived connections
       if (
         record.outgoingClosedTime &&
         !record.incoming.destroyed &&
         !record.connectionClosed &&
-        now - record.outgoingClosedTime > 120000
+        now - record.outgoingClosedTime > 1800000  // 30 minutes
       ) {
-        logger.log('warn', `Parity check failed: ${record.remoteIP}`, {
-          connectionId,
-          remoteIP: record.remoteIP,
-          timeElapsed: plugins.prettyMs(now - record.outgoingClosedTime),
-          component: 'connection-manager'
-        });
-        this.cleanupConnection(record, 'parity_check');
+        // Only close if no data activity for 10 minutes
+        if (now - record.lastActivity > 600000) {
+          logger.log('warn', `Parity check failed after extended timeout: ${record.remoteIP}`, {
+            connectionId,
+            remoteIP: record.remoteIP,
+            timeElapsed: plugins.prettyMs(now - record.outgoingClosedTime),
+            inactiveFor: plugins.prettyMs(now - record.lastActivity),
+            component: 'connection-manager'
+          });
+          this.cleanupConnection(record, 'parity_check');
+        }
       }
     }
   }
@@ -537,13 +567,18 @@ export class ConnectionManager extends LifecycleComponent {
           }
 
           // Immediate destruction using socket-utils
+          const shutdownPromises: Promise<void>[] = [];
+          
           if (record.incoming) {
-            cleanupSocket(record.incoming, `${record.id}-incoming-shutdown`);
+            shutdownPromises.push(cleanupSocket(record.incoming, `${record.id}-incoming-shutdown`, { immediate: true }));
           }
 
           if (record.outgoing) {
-            cleanupSocket(record.outgoing, `${record.id}-outgoing-shutdown`);
+            shutdownPromises.push(cleanupSocket(record.outgoing, `${record.id}-outgoing-shutdown`, { immediate: true }));
           }
+          
+          // Don't wait for shutdown cleanup in this batch processing
+          Promise.all(shutdownPromises).catch(() => {});
         } catch (err) {
           logger.log('error', `Error during connection cleanup: ${err}`, { 
             connectionId: record.id, 

ts/proxies/smart-proxy/http-proxy-bridge.ts

@@ -1,5 +1,6 @@
 import * as plugins from '../../plugins.js';
 import { HttpProxy } from '../http-proxy/index.js';
+import { setupBidirectionalForwarding } from '../../core/utils/socket-utils.js';
 import type { IConnectionRecord, ISmartProxyOptions } from './models/interfaces.js';
 import type { IRouteConfig } from './models/route-types.js';
 
@@ -123,36 +124,25 @@ export class HttpProxyBridge {
       proxySocket.write(initialChunk);
     }
     
-    // Pipe the sockets together
-    socket.pipe(proxySocket);
-    proxySocket.pipe(socket);
-    
-    // Handle cleanup
-    let cleanedUp = false;
-    const cleanup = (reason: string) => {
-      if (cleanedUp) return;
-      cleanedUp = true;
-      
-      // Remove all event listeners to prevent memory leaks
-      socket.removeAllListeners('end');
-      socket.removeAllListeners('error');
-      proxySocket.removeAllListeners('end');
-      proxySocket.removeAllListeners('error');
-      
-      socket.unpipe(proxySocket);
-      proxySocket.unpipe(socket);
-      
-      if (!proxySocket.destroyed) {
-        proxySocket.destroy();
-      }
-      
-      cleanupCallback(reason);
-    };
-    
-    socket.on('end', () => cleanup('socket_end'));
-    socket.on('error', () => cleanup('socket_error'));
-    proxySocket.on('end', () => cleanup('proxy_end'));
-    proxySocket.on('error', () => cleanup('proxy_error'));
+    // Use centralized bidirectional forwarding
+    setupBidirectionalForwarding(socket, proxySocket, {
+      onClientData: (chunk) => {
+        // Update stats if needed
+        if (record) {
+          record.bytesReceived += chunk.length;
+        }
+      },
+      onServerData: (chunk) => {
+        // Update stats if needed
+        if (record) {
+          record.bytesSent += chunk.length;
+        }
+      },
+      onCleanup: (reason) => {
+        cleanupCallback(reason);
+      },
+      enableHalfOpen: false // Close both when one closes (required for proxy chains)
+    });
   }
   
   /**

ts/proxies/smart-proxy/port-manager.ts

@@ -65,7 +65,7 @@ export class PortManager {
     const server = plugins.net.createServer((socket) => {
       // Check if shutting down
       if (this.isShuttingDown) {
-        cleanupSocket(socket, 'port-manager-shutdown');
+        cleanupSocket(socket, 'port-manager-shutdown', { immediate: true });
         return;
       }
       

ts/proxies/smart-proxy/route-connection-handler.ts

@@ -9,7 +9,7 @@ import { TlsManager } from './tls-manager.js';
 import { HttpProxyBridge } from './http-proxy-bridge.js';
 import { TimeoutManager } from './timeout-manager.js';
 import { RouteManager } from './route-manager.js';
-import { cleanupSocket } from '../../core/utils/socket-utils.js';
+import { cleanupSocket, createIndependentSocketHandlers, setupSocketHandlers, createSocketWithErrorHandler, setupBidirectionalForwarding } from '../../core/utils/socket-utils.js';
 
 /**
  * Handles new connection processing and setup logic with support for route-based configuration
@@ -84,12 +84,16 @@ export class RouteConnectionHandler {
     const ipValidation = this.securityManager.validateIP(remoteIP);
     if (!ipValidation.allowed) {
       logger.log('warn', `Connection rejected`, { remoteIP, reason: ipValidation.reason, component: 'route-handler' });
-      cleanupSocket(socket, `rejected-${ipValidation.reason}`);
+      cleanupSocket(socket, `rejected-${ipValidation.reason}`, { immediate: true });
       return;
     }
 
     // Create a new connection record
     const record = this.connectionManager.createConnection(socket);
+    if (!record) {
+      // Connection was rejected due to limit - socket already destroyed by connection manager
+      return;
+    }
     const connectionId = record.id;
 
     // Apply socket optimizations
@@ -172,8 +176,33 @@ export class RouteConnectionHandler {
 
     // If no routes require TLS handling and it's not port 443, route immediately
     if (!needsTlsHandling && localPort !== 443) {
-      // Set up error handler
-      socket.on('error', this.connectionManager.handleError('incoming', record));
+      // Set up proper socket handlers for immediate routing
+      setupSocketHandlers(
+        socket,
+        (reason) => {
+          // Only cleanup if connection hasn't been fully established
+          // Check if outgoing connection exists and is connected
+          if (!record.outgoing || record.outgoing.readyState !== 'open') {
+            logger.log('debug', `Connection ${connectionId} closed during immediate routing: ${reason}`, {
+              connectionId,
+              remoteIP: record.remoteIP,
+              reason,
+              hasOutgoing: !!record.outgoing,
+              outgoingState: record.outgoing?.readyState,
+              component: 'route-handler'
+            });
+            
+            // If there's a pending outgoing connection, destroy it
+            if (record.outgoing && !record.outgoing.destroyed) {
+              record.outgoing.destroy();
+            }
+            
+            this.connectionManager.cleanupConnection(record, reason);
+          }
+        },
+        undefined, // Use default timeout handler
+        'immediate-route-client'
+      );
       
       // Route immediately for non-TLS connections
       this.routeConnection(socket, record, '', undefined);
@@ -217,6 +246,37 @@ export class RouteConnectionHandler {
     // Set up error handler
     socket.on('error', this.connectionManager.handleError('incoming', record));
 
+    // Add close/end handlers to catch immediate disconnections
+    socket.once('close', () => {
+      if (!initialDataReceived) {
+        logger.log('warn', `Connection ${connectionId} closed before sending initial data`, {
+          connectionId,
+          remoteIP: record.remoteIP,
+          component: 'route-handler'
+        });
+        if (initialTimeout) {
+          clearTimeout(initialTimeout);
+          initialTimeout = null;
+        }
+        this.connectionManager.cleanupConnection(record, 'closed_before_data');
+      }
+    });
+
+    socket.once('end', () => {
+      if (!initialDataReceived) {
+        logger.log('debug', `Connection ${connectionId} ended before sending initial data`, {
+          connectionId,
+          remoteIP: record.remoteIP,
+          component: 'route-handler'
+        });
+        if (initialTimeout) {
+          clearTimeout(initialTimeout);
+          initialTimeout = null;
+        }
+        // Don't cleanup on 'end' - wait for 'close'
+      }
+    });
+
     // First data handler to capture initial TLS handshake
     socket.once('data', (chunk: Buffer) => {
       // Clear the initial timeout since we've received data
@@ -546,6 +606,12 @@ export class RouteConnectionHandler {
       
       // We don't close the socket - just let it remain open
       // The kernel-level NFTables rules will handle the actual forwarding
+      
+      // Set up cleanup when the socket eventually closes
+      socket.once('close', () => {
+        this.connectionManager.cleanupConnection(record, 'nftables_closed');
+      });
+      
       return;
     }
 
@@ -687,7 +753,7 @@ export class RouteConnectionHandler {
                 record,
                 initialChunk,
                 this.settings.httpProxyPort || 8443,
-                (reason) => this.connectionManager.initiateCleanupOnce(record, reason)
+                (reason) => this.connectionManager.cleanupConnection(record, reason)
               );
               return;
             }
@@ -742,7 +808,7 @@ export class RouteConnectionHandler {
           record,
           initialChunk,
           this.settings.httpProxyPort || 8443,
-          (reason) => this.connectionManager.initiateCleanupOnce(record, reason)
+          (reason) => this.connectionManager.cleanupConnection(record, reason)
         );
         return;
       } else {
@@ -917,106 +983,6 @@ export class RouteConnectionHandler {
     }
   }
 
-  /**
-   * Setup improved error handling for the outgoing connection
-   */
-  private setupOutgoingErrorHandler(
-    connectionId: string,
-    targetSocket: plugins.net.Socket, 
-    record: IConnectionRecord,
-    socket: plugins.net.Socket,
-    finalTargetHost: string,
-    finalTargetPort: number
-  ): void {
-    targetSocket.once('error', (err) => {
-      // This handler runs only once during the initial connection phase
-      const code = (err as any).code;
-      logger.log('error', 
-        `Connection setup error for ${connectionId} to ${finalTargetHost}:${finalTargetPort}: ${err.message} (${code})`, 
-        {
-          connectionId,
-          targetHost: finalTargetHost,
-          targetPort: finalTargetPort,
-          errorMessage: err.message,
-          errorCode: code,
-          component: 'route-handler'
-        }
-      );
-
-      // Resume the incoming socket to prevent it from hanging
-      socket.resume();
-
-      // Log specific error types for easier debugging
-      if (code === 'ECONNREFUSED') {
-        logger.log('error', 
-          `Connection ${connectionId}: Target ${finalTargetHost}:${finalTargetPort} refused connection. Check if the target service is running and listening on that port.`, 
-          {
-            connectionId,
-            targetHost: finalTargetHost,
-            targetPort: finalTargetPort,
-            recommendation: 'Check if the target service is running and listening on that port.',
-            component: 'route-handler'
-          }
-        );
-      } else if (code === 'ETIMEDOUT') {
-        logger.log('error', 
-          `Connection ${connectionId} to ${finalTargetHost}:${finalTargetPort} timed out. Check network conditions, firewall rules, or if the target is too far away.`, 
-          {
-            connectionId,
-            targetHost: finalTargetHost,
-            targetPort: finalTargetPort,
-            recommendation: 'Check network conditions, firewall rules, or if the target is too far away.',
-            component: 'route-handler'
-          }
-        );
-      } else if (code === 'ECONNRESET') {
-        logger.log('error', 
-          `Connection ${connectionId} to ${finalTargetHost}:${finalTargetPort} was reset. The target might have closed the connection abruptly.`, 
-          {
-            connectionId,
-            targetHost: finalTargetHost,
-            targetPort: finalTargetPort,
-            recommendation: 'The target might have closed the connection abruptly.',
-            component: 'route-handler'
-          }
-        );
-      } else if (code === 'EHOSTUNREACH') {
-        logger.log('error', 
-          `Connection ${connectionId}: Host ${finalTargetHost} is unreachable. Check DNS settings, network routing, or firewall rules.`, 
-          {
-            connectionId,
-            targetHost: finalTargetHost,
-            recommendation: 'Check DNS settings, network routing, or firewall rules.',
-            component: 'route-handler'
-          }
-        );
-      } else if (code === 'ENOTFOUND') {
-        logger.log('error', 
-          `Connection ${connectionId}: DNS lookup failed for ${finalTargetHost}. Check your DNS settings or if the hostname is correct.`, 
-          {
-            connectionId,
-            targetHost: finalTargetHost,
-            recommendation: 'Check your DNS settings or if the hostname is correct.',
-            component: 'route-handler'
-          }
-        );
-      }
-
-      // Clear any existing error handler after connection phase
-      targetSocket.removeAllListeners('error');
-
-      // Re-add the normal error handler for established connections
-      targetSocket.on('error', this.connectionManager.handleError('outgoing', record));
-
-      if (record.outgoingTerminationReason === null) {
-        record.outgoingTerminationReason = 'connection_failed';
-        this.connectionManager.incrementTerminationStat('outgoing', 'connection_failed');
-      }
-
-      // Clean up the connection
-      this.connectionManager.initiateCleanupOnce(record, `connection_failed_${code}`);
-    });
-  }
 
   /**
    * Sets up a direct connection to the target
@@ -1073,8 +1039,191 @@ export class RouteConnectionHandler {
       record.pendingDataSize = initialChunk.length;
     }
 
-    // Create the target socket
-    const targetSocket = plugins.net.connect(connectionOptions);
+    // Create the target socket with immediate error handling
+    const targetSocket = createSocketWithErrorHandler({
+      port: finalTargetPort,
+      host: finalTargetHost,
+      onError: (error) => {
+        // Connection failed - clean up everything immediately
+        // Check if connection record is still valid (client might have disconnected)
+        if (record.connectionClosed) {
+          logger.log('debug', `Backend connection failed but client already disconnected for ${connectionId}`, {
+            connectionId,
+            errorCode: (error as any).code,
+            component: 'route-handler'
+          });
+          return;
+        }
+        
+        logger.log('error', 
+          `Connection setup error for ${connectionId} to ${finalTargetHost}:${finalTargetPort}: ${error.message} (${(error as any).code})`, 
+          {
+            connectionId,
+            targetHost: finalTargetHost,
+            targetPort: finalTargetPort,
+            errorMessage: error.message,
+            errorCode: (error as any).code,
+            component: 'route-handler'
+          }
+        );
+        
+        // Log specific error types for easier debugging
+        if ((error as any).code === 'ECONNREFUSED') {
+          logger.log('error', 
+            `Connection ${connectionId}: Target ${finalTargetHost}:${finalTargetPort} refused connection. Check if the target service is running and listening on that port.`, 
+            {
+              connectionId,
+              targetHost: finalTargetHost,
+              targetPort: finalTargetPort,
+              recommendation: 'Check if the target service is running and listening on that port.',
+              component: 'route-handler'
+            }
+          );
+        }
+        
+        // Resume the incoming socket to prevent it from hanging
+        if (socket && !socket.destroyed) {
+          socket.resume();
+        }
+        
+        // Clean up the incoming socket
+        if (socket && !socket.destroyed) {
+          socket.destroy();
+        }
+        
+        // Clean up the connection record - this is critical!
+        this.connectionManager.cleanupConnection(record, `connection_failed_${(error as any).code || 'unknown'}`);
+      },
+      onConnect: () => {
+        if (this.settings.enableDetailedLogging) {
+          logger.log('info', `Connection ${connectionId} established to target ${finalTargetHost}:${finalTargetPort}`, {
+            connectionId,
+            targetHost: finalTargetHost,
+            targetPort: finalTargetPort,
+            component: 'route-handler'
+          });
+        }
+        
+        // Clear any error listeners added by createSocketWithErrorHandler
+        targetSocket.removeAllListeners('error');
+        
+        // Add the normal error handler for established connections
+        targetSocket.on('error', this.connectionManager.handleError('outgoing', record));
+        
+        // Flush any pending data to target
+        if (record.pendingData.length > 0) {
+          const combinedData = Buffer.concat(record.pendingData);
+
+          if (this.settings.enableDetailedLogging) {
+            console.log(
+              `[${connectionId}] Forwarding ${combinedData.length} bytes of initial data to target`
+            );
+          }
+
+          // Write pending data immediately
+          targetSocket.write(combinedData, (err) => {
+            if (err) {
+              logger.log('error', `Error writing pending data to target for connection ${connectionId}: ${err.message}`, {
+                connectionId,
+                error: err.message,
+                component: 'route-handler'
+              });
+              return this.connectionManager.cleanupConnection(record, 'write_error');
+            }
+          });
+
+          // Clear the buffer now that we've processed it
+          record.pendingData = [];
+          record.pendingDataSize = 0;
+        }
+
+        // Use centralized bidirectional forwarding setup
+        setupBidirectionalForwarding(socket, targetSocket, {
+          onClientData: (chunk) => {
+            record.bytesReceived += chunk.length;
+            this.timeoutManager.updateActivity(record);
+          },
+          onServerData: (chunk) => {
+            record.bytesSent += chunk.length;
+            this.timeoutManager.updateActivity(record);
+          },
+          onCleanup: (reason) => {
+            this.connectionManager.cleanupConnection(record, reason);
+          },
+          enableHalfOpen: false // Default: close both when one closes (required for proxy chains)
+        });
+        
+        // Apply timeouts if keep-alive is enabled
+        if (record.hasKeepAlive) {
+          socket.setTimeout(this.settings.socketTimeout || 3600000);
+          targetSocket.setTimeout(this.settings.socketTimeout || 3600000);
+        }
+
+        // Log successful connection
+        logger.log('info', 
+          `Connection established: ${record.remoteIP} -> ${finalTargetHost}:${finalTargetPort}` +
+          `${serverName ? ` (SNI: ${serverName})` : record.lockedDomain ? ` (Domain: ${record.lockedDomain})` : ''}`, 
+          {
+            remoteIP: record.remoteIP,
+            targetHost: finalTargetHost,
+            targetPort: finalTargetPort,
+            sni: serverName || undefined,
+            domain: !serverName && record.lockedDomain ? record.lockedDomain : undefined,
+            component: 'route-handler'
+          }
+        );
+
+        // Add TLS renegotiation handler if needed
+        if (serverName) {
+          // Create connection info object for the existing connection
+          const connInfo = {
+            sourceIp: record.remoteIP,
+            sourcePort: record.incoming.remotePort || 0,
+            destIp: record.incoming.localAddress || '',
+            destPort: record.incoming.localPort || 0,
+          };
+
+          // Create a renegotiation handler function
+          const renegotiationHandler = this.tlsManager.createRenegotiationHandler(
+            connectionId,
+            serverName,
+            connInfo,
+            (_connectionId, reason) => this.connectionManager.cleanupConnection(record, reason)
+          );
+
+          // Store the handler in the connection record so we can remove it during cleanup
+          record.renegotiationHandler = renegotiationHandler;
+
+          // Add the handler to the socket
+          socket.on('data', renegotiationHandler);
+
+          if (this.settings.enableDetailedLogging) {
+            logger.log('info', `TLS renegotiation handler installed for connection ${connectionId} with SNI ${serverName}`, {
+              connectionId,
+              serverName,
+              component: 'route-handler'
+            });
+          }
+        }
+
+        // Set connection timeout
+        record.cleanupTimer = this.timeoutManager.setupConnectionTimeout(record, (record, reason) => {
+          logger.log('warn', `Connection ${connectionId} from ${record.remoteIP} exceeded max lifetime, forcing cleanup`, {
+            connectionId,
+            remoteIP: record.remoteIP,
+            component: 'route-handler'
+          });
+          this.connectionManager.cleanupConnection(record, reason);
+        });
+
+        // Mark TLS handshake as complete for TLS connections
+        if (record.isTLS) {
+          record.tlsHandshakeComplete = true;
+        }
+      }
+    });
+    
+    // Set outgoing socket immediately so it can be cleaned up if client disconnects
     record.outgoing = targetSocket;
     record.outgoingStartTime = Date.now();
 
@@ -1107,13 +1256,6 @@ export class RouteConnectionHandler {
       }
     }
 
-    // Setup improved error handling for outgoing connection
-    this.setupOutgoingErrorHandler(connectionId, targetSocket, record, socket, finalTargetHost, finalTargetPort);
-
-    // Setup close handlers
-    targetSocket.on('close', this.connectionManager.handleClose('outgoing', record));
-    socket.on('close', this.connectionManager.handleClose('incoming', record));
-    
     // Setup error handlers for incoming socket
     socket.on('error', this.connectionManager.handleError('incoming', record));
 
@@ -1142,7 +1284,7 @@ export class RouteConnectionHandler {
         record.incomingTerminationReason = 'timeout';
         this.connectionManager.incrementTerminationStat('incoming', 'timeout');
       }
-      this.connectionManager.initiateCleanupOnce(record, 'timeout_incoming');
+      this.connectionManager.cleanupConnection(record, 'timeout_incoming');
     });
 
     targetSocket.on('timeout', () => {
@@ -1169,133 +1311,10 @@ export class RouteConnectionHandler {
         record.outgoingTerminationReason = 'timeout';
         this.connectionManager.incrementTerminationStat('outgoing', 'timeout');
       }
-      this.connectionManager.initiateCleanupOnce(record, 'timeout_outgoing');
+      this.connectionManager.cleanupConnection(record, 'timeout_outgoing');
     });
 
     // Apply socket timeouts
     this.timeoutManager.applySocketTimeouts(record);
-
-    // Track outgoing data for bytes counting
-    targetSocket.on('data', (chunk: Buffer) => {
-      record.bytesSent += chunk.length;
-      this.timeoutManager.updateActivity(record);
-    });
-
-    // Wait for the outgoing connection to be ready before setting up piping
-    targetSocket.once('connect', () => {
-      if (this.settings.enableDetailedLogging) {
-        logger.log('info', `Connection ${connectionId} established to target ${finalTargetHost}:${finalTargetPort}`, {
-          connectionId,
-          targetHost: finalTargetHost,
-          targetPort: finalTargetPort,
-          component: 'route-handler'
-        });
-      }
-
-      // Clear the initial connection error handler
-      targetSocket.removeAllListeners('error');
-
-      // Add the normal error handler for established connections
-      targetSocket.on('error', this.connectionManager.handleError('outgoing', record));
-
-      // Flush any pending data to target
-      if (record.pendingData.length > 0) {
-        const combinedData = Buffer.concat(record.pendingData);
-
-        if (this.settings.enableDetailedLogging) {
-          console.log(
-            `[${connectionId}] Forwarding ${combinedData.length} bytes of initial data to target`
-          );
-        }
-
-        // Write pending data immediately
-        targetSocket.write(combinedData, (err) => {
-          if (err) {
-            logger.log('error', `Error writing pending data to target for connection ${connectionId}: ${err.message}`, {
-              connectionId,
-              error: err.message,
-              component: 'route-handler'
-            });
-            return this.connectionManager.initiateCleanupOnce(record, 'write_error');
-          }
-        });
-
-        // Clear the buffer now that we've processed it
-        record.pendingData = [];
-        record.pendingDataSize = 0;
-      }
-
-      // Immediately setup bidirectional piping - much simpler than manual data management
-      socket.pipe(targetSocket);
-      targetSocket.pipe(socket);
-
-      // Track incoming data for bytes counting - do this after piping is set up
-      socket.on('data', (chunk: Buffer) => {
-        record.bytesReceived += chunk.length;
-        this.timeoutManager.updateActivity(record);
-      });
-
-      // Log successful connection
-      logger.log('info', 
-        `Connection established: ${record.remoteIP} -> ${finalTargetHost}:${finalTargetPort}` +
-        `${serverName ? ` (SNI: ${serverName})` : record.lockedDomain ? ` (Domain: ${record.lockedDomain})` : ''}`, 
-        {
-          remoteIP: record.remoteIP,
-          targetHost: finalTargetHost,
-          targetPort: finalTargetPort,
-          sni: serverName || undefined,
-          domain: !serverName && record.lockedDomain ? record.lockedDomain : undefined,
-          component: 'route-handler'
-        }
-      );
-
-      // Add TLS renegotiation handler if needed
-      if (serverName) {
-        // Create connection info object for the existing connection
-        const connInfo = {
-          sourceIp: record.remoteIP,
-          sourcePort: record.incoming.remotePort || 0,
-          destIp: record.incoming.localAddress || '',
-          destPort: record.incoming.localPort || 0,
-        };
-
-        // Create a renegotiation handler function
-        const renegotiationHandler = this.tlsManager.createRenegotiationHandler(
-          connectionId,
-          serverName,
-          connInfo,
-          (_connectionId, reason) => this.connectionManager.initiateCleanupOnce(record, reason)
-        );
-
-        // Store the handler in the connection record so we can remove it during cleanup
-        record.renegotiationHandler = renegotiationHandler;
-
-        // Add the handler to the socket
-        socket.on('data', renegotiationHandler);
-
-        if (this.settings.enableDetailedLogging) {
-          logger.log('info', `TLS renegotiation handler installed for connection ${connectionId} with SNI ${serverName}`, {
-            connectionId,
-            serverName,
-            component: 'route-handler'
-          });
-        }
-      }
-
-      // Set connection timeout
-      record.cleanupTimer = this.timeoutManager.setupConnectionTimeout(record, (record, reason) => {
-        logger.log('warn', `Connection ${connectionId} from ${record.remoteIP} exceeded max lifetime, forcing cleanup`, {
-          connectionId,
-          remoteIP: record.remoteIP,
-          component: 'route-handler'
-        });
-        this.connectionManager.initiateCleanupOnce(record, reason);
-      });
-
-      // Mark TLS handshake as complete for TLS connections
-      if (record.isTLS) {
-        record.tlsHandshakeComplete = true;
-      }
-    });
   }
 }