diff --git a/src/__tests__/proxy.integration.test.ts b/src/__tests__/proxy.integration.test.ts
index 30b16a66..79a4580f 100644
--- a/src/__tests__/proxy.integration.test.ts
+++ b/src/__tests__/proxy.integration.test.ts
@@ -820,6 +820,38 @@ describe('Proxy usage recording – finish vs premature close', () => {
     void fetchError;
   });
 
+  it('terminates the client stream when upstream fails after headers were flushed', async () => {
+    // Upstream promises 1000 bytes, sends a few, then resets the socket.
+    // Headers have already been flushed to the caller by then, so the error
+    // handler cannot send a 502; it must destroy the response so the caller
+    // sees an aborted stream instead of hanging or accepting a partial body.
+    setUpstreamHandler((_req, res) => {
+      res.writeHead(200, { 'content-type': 'application/json', 'content-length': '1000' });
+      res.write('{"partial":');
+      setTimeout(() => res.socket!.destroy(), 20);
+    });
+
+    const outcome = await Promise.race([
+      (async () => {
+        const res = await fetch(`${proxyUrl}/v1/call/${TEST_API_SLUG}/mid-stream-terminate`, {
+          method: 'GET',
+          headers: { 'x-api-key': TEST_API_KEY },
+        });
+        return res.text().then(
+          () => 'completed' as const,
+          () => 'terminated' as const,
+        );
+      })().catch(() => 'terminated' as const),
+      new Promise<'hung'>((resolve) => setTimeout(() => resolve('hung'), 3000)),
+    ]);
+
+    expect(outcome).toBe('terminated');
+
+    await new Promise((resolve) => setTimeout(resolve, 50));
+    expect(usageStore.getEvents()).toHaveLength(0);
+    expect(billing.getBalance(TEST_DEVELOPER_ID)).toBe(1000);
+  });
+
   it('does NOT double-count when the same requestId is seen twice', async () => {
     // Simulates a retry or duplicate delivery of the same logical request.
     const res1 = await fetch(`${proxyUrl}/v1/call/${TEST_API_SLUG}/idempotency-test`, {
diff --git a/src/middleware/errorHandler.contract.test.ts b/src/middleware/errorHandler.contract.test.ts
index 41f99521..cc6a236c 100644
--- a/src/middleware/errorHandler.contract.test.ts
+++ b/src/middleware/errorHandler.contract.test.ts
@@ -5,9 +5,12 @@ import { ValidationError } from './validate.js';
 import { errorHandler } from './errorHandler.js';
 
 function response() {
-  const result = { statusCode: 200, body: undefined as unknown, sent: false };
+  const result = { statusCode: 200, body: undefined as unknown, sent: false, destroyedWith: undefined as unknown };
   const value = {
     headersSent: false,
+    writableEnded: false,
+    destroyed: false,
+    destroy(err?: unknown) { result.destroyedWith = err; value.destroyed = true; return value; },
     status(code: number) { result.statusCode = code; return value; },
     json(body: unknown) { result.body = body; result.sent = true; return value; },
   } as unknown as Response;
@@ -113,8 +116,11 @@ describe('errorHandler contract', () => {
   it('does not overwrite a response that already sent headers', () => {
     const output = response();
     (output.value as Response).headersSent = true;
-    errorHandler(new Error('already handled'), request(), output.value, jest.fn() as unknown as NextFunction);
+    const failure = new Error('already handled');
+    errorHandler(failure, request(), output.value, jest.fn() as unknown as NextFunction);
     expect(output.result.sent).toBe(false);
+    // Nothing can be written after headers, so the stream is terminated instead.
+    expect(output.result.destroyedWith).toBe(failure);
   });
 
   it('keeps error responses JSON-compatible for null and non-Error throws', () => {
diff --git a/src/middleware/errorHandler.test.ts b/src/middleware/errorHandler.test.ts
index 6409e1a9..20a9ddf5 100644
--- a/src/middleware/errorHandler.test.ts
+++ b/src/middleware/errorHandler.test.ts
@@ -1,4 +1,8 @@
-import { Request, Response, NextFunction } from 'express';import { errorHandler } from '../middleware/errorHandler.js';
+import express, { Request, Response, NextFunction } from 'express';
+import http from 'node:http';
+import type { Server } from 'node:http';
+import type { AddressInfo } from 'node:net';
+import { errorHandler } from '../middleware/errorHandler.js';
 import { 
   BadRequestError, 
   UnauthorizedError,
@@ -8,7 +12,8 @@ import {
   TooManyRequestsError,
   AppError,
 } from '../errors/index.js';
-import { ValidationError } from '../middleware/validate.js';import { logger } from '../logger.js';
+import { ValidationError } from '../middleware/validate.js';
+import { logger } from '../logger.js';
 import type { ErrorEnvelope } from '../types/ResponseEnvelope.js';
 
 jest.mock('../logger.js', () => ({
@@ -62,7 +67,7 @@ describe('Error Handler', () => {
       code: 'BAD_REQUEST',
       message: 'Test bad request',
     });
-    expect(typeof call.timestamp).toBe(typeof 'string');
+    expect(typeof call.timestamp).toBe('string');
 
     expect(logger.error).toHaveBeenCalledWith(
       '[errorHandler]',
@@ -125,19 +130,142 @@ describe('Error Handler', () => {
     expect(call.requestId).toBe('unknown');
   });
 
-  it('should not send response if headers already sent', () => {
-    mockRes.headersSent = true;
-    const error = new BadRequestError('Test error');
-    
-    errorHandler(
-      error,
-      mockReq as Request,
-      mockRes as Response<ErrorEnvelope>,
-      mockNext
-    );
+  describe('when headers were already sent (mid-stream failure)', () => {
+    let destroy: jest.Mock;
 
-    expect(mockRes.status).not.toHaveBeenCalled();
-    expect(mockRes.json).not.toHaveBeenCalled();
+    beforeEach(() => {
+      destroy = jest.fn();
+      Object.assign(mockRes, {
+        headersSent: true,
+        writableEnded: false,
+        destroyed: false,
+        destroy,
+      });
+    });
+
+    it('does not write an envelope and destroys the response with the error', () => {
+      const error = new Error('upstream reset mid-stream');
+
+      errorHandler(error, mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext);
+
+      expect(mockRes.status).not.toHaveBeenCalled();
+      expect(mockRes.json).not.toHaveBeenCalled();
+      expect(destroy).toHaveBeenCalledTimes(1);
+      expect(destroy).toHaveBeenCalledWith(error);
+    });
+
+    it('logs the error exactly once with the requestId', () => {
+      errorHandler(new Error('boom'), mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext);
+
+      expect(logger.error).toHaveBeenCalledTimes(1);
+      expect(logger.error).toHaveBeenCalledWith(
+        '[errorHandler]',
+        expect.objectContaining({ requestId: 'test-request-id', headersSent: true }),
+      );
+    });
+
+    it('does not delegate to next(err), which would log a second time', () => {
+      errorHandler(new Error('boom'), mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext);
+
+      expect(mockNext).not.toHaveBeenCalled();
+    });
+
+    it('wraps non-Error throws so destroy always receives an Error', () => {
+      errorHandler('string failure', mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext);
+
+      expect(destroy).toHaveBeenCalledWith(expect.any(Error));
+      expect((destroy.mock.calls[0][0] as Error).message).toBe('string failure');
+    });
+
+    it('maps AppErrors thrown mid-stream to a destroy, not a status change', () => {
+      errorHandler(new BadRequestError('late'), mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext);
+
+      expect(mockRes.status).not.toHaveBeenCalled();
+      expect(destroy).toHaveBeenCalledTimes(1);
+    });
+
+    it('leaves a cleanly ended response alone but still logs', () => {
+      (mockRes as { writableEnded: boolean }).writableEnded = true;
+
+      errorHandler(new Error('after end'), mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext);
+
+      expect(destroy).not.toHaveBeenCalled();
+      expect(logger.error).toHaveBeenCalledTimes(1);
+    });
+
+    it('does not destroy twice when the client already disconnected', () => {
+      (mockRes as { destroyed: boolean }).destroyed = true;
+
+      errorHandler(new Error('client gone'), mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext);
+
+      expect(destroy).not.toHaveBeenCalled();
+      expect(logger.error).toHaveBeenCalledTimes(1);
+    });
+
+    it('never throws if destroy itself fails', () => {
+      destroy.mockImplementation(() => {
+        throw new Error('destroy failed');
+      });
+
+      expect(() =>
+        errorHandler(new Error('boom'), mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext),
+      ).not.toThrow();
+      expect(logger.error).toHaveBeenCalledTimes(1);
+      expect(logger.warn).toHaveBeenCalledWith(
+        '[errorHandler] failed to destroy response after headers sent',
+        expect.objectContaining({ requestId: 'test-request-id' }),
+      );
+    });
+  });
+
+  it('leaves responses without headers sent unchanged (no destroy)', () => {
+    const destroy = jest.fn();
+    Object.assign(mockRes, { destroy, writableEnded: false, destroyed: false });
+
+    errorHandler(new BadRequestError('Test error'), mockReq as Request, mockRes as Response<ErrorEnvelope>, mockNext);
+
+    expect(mockRes.status).toHaveBeenCalledWith(400);
+    expect(mockRes.json).toHaveBeenCalledTimes(1);
+    expect(destroy).not.toHaveBeenCalled();
+  });
+
+  it('terminates a real socket when a handler throws after res.write', async () => {
+    const app = express();
+    app.use((req, _res, next) => {
+      (req as Request & { id?: string }).id = 'real-socket-id';
+      next();
+    });
+    app.get('/stream', (_req, res, next) => {
+      res.status(200).set('content-length', '1000');
+      res.write('{"partial":');
+      setImmediate(() => next(new Error('failed after first chunk')));
+    });
+    app.use(errorHandler);
+
+    const server: Server = await new Promise((resolve) => {
+      const s = app.listen(0, () => resolve(s));
+    });
+
+    try {
+      const { port } = server.address() as AddressInfo;
+      const outcome = await new Promise<'aborted' | 'completed'>((resolve) => {
+        const timeout = setTimeout(() => resolve('completed'), 2000);
+        http
+          .get({ port, path: '/stream', agent: false }, (res) => {
+            res.on('data', () => undefined);
+            res.on('end', () => { clearTimeout(timeout); resolve('completed'); });
+            res.on('aborted', () => { clearTimeout(timeout); resolve('aborted'); });
+            res.on('error', () => { clearTimeout(timeout); resolve('aborted'); });
+            res.on('close', () => { clearTimeout(timeout); resolve(res.complete ? 'completed' : 'aborted'); });
+          })
+          .on('error', () => { clearTimeout(timeout); resolve('aborted'); });
+      });
+
+      expect(outcome).toBe('aborted');
+      expect(logger.error).toHaveBeenCalledTimes(1);
+    } finally {
+      await new Promise<void>((resolve) => server.close(() => resolve()));
+    }
   });
 
   it('should destroy the socket when headers are already sent', () => {
diff --git a/src/middleware/errorHandler.ts b/src/middleware/errorHandler.ts
index 23257ef3..83b07187 100644
--- a/src/middleware/errorHandler.ts
+++ b/src/middleware/errorHandler.ts
@@ -25,14 +25,44 @@ function extractValidationDetails(err: unknown): ValidationErrorDetail[] | undef
   return undefined;
 }
 
+/**
+ * Terminate a response whose headers were already flushed.
+ *
+ * Once headers are out we can no longer send a JSON error envelope: writing one
+ * would corrupt the in-flight body, and simply returning leaves the client with
+ * a truncated stream that looks complete (or hangs until its own timeout) while
+ * the socket leaks. Destroying the response makes the client observe an aborted
+ * stream instead.
+ *
+ * - No-op if the response already ended cleanly or was already destroyed
+ *   (e.g. the client disconnected first), so we never double-destroy or kill a
+ *   keep-alive socket that completed successfully.
+ * - Never throws: an error handler must not raise a second error.
+ */
+function terminateAfterHeadersSent(res: Response<ErrorEnvelope>, err: unknown, requestId: string): void {
+  if (res.writableEnded || res.destroyed) {
+    return;
+  }
+
+  try {
+    res.destroy(err instanceof Error ? err : new Error(typeof err === 'string' ? err : 'Response aborted after headers were sent'));
+  } catch (destroyErr) {
+    logger.warn('[errorHandler] failed to destroy response after headers sent', {
+      requestId,
+      message: destroyErr instanceof Error ? destroyErr.message : String(destroyErr),
+    });
+  }
+}
+
 /**
  * Global error-handling middleware (4-arg form).
  * - Catches errors thrown in routes/services
  * - Maps known AppError subclasses to HTTP status codes
  * - Returns consistent JSON envelope: { success: false, error: { code, message }, requestId, timestamp }
  * - Never sends stack traces to the client in production
- * - Logs full error server-side
- * - When headers are already sent, destroys the socket so the client sees a terminated stream
+ * - Logs full error server-side (exactly once, with requestId)
+ * - If headers were already sent (mid-stream failure), the error is logged and
+ *   the response/socket is destroyed so the client sees a terminated stream
  */
 export function errorHandler(
   err: unknown,
@@ -77,20 +107,16 @@ export function errorHandler(
     normalized.simulationDetails,
   );
 
-  if (!res.headersSent) {
+  const headersAlreadySent = res.headersSent;
+
+  if (!headersAlreadySent) {
     res.status(statusCode).json(body);
-  } else {
-    // Headers already flushed: we cannot write a JSON envelope.
-    // Terminate the socket so the client observes a truncated stream
-    // instead of hanging until its own timeout.
-    if (typeof res.destroy === 'function') {
-      res.destroy(err instanceof Error ? err : undefined);
-    }
   }
 
   const logData = {
     requestId,
     statusCode,
+    ...(headersAlreadySent ? { headersSent: true } : {}),
     message: rawMessage,
     ...(isProduction ? {} : { err }),
   };
@@ -104,4 +130,10 @@ export function errorHandler(
   } else {
     logger.error("[errorHandler]", logData);
   }
+
+  // Log first, then terminate, so the error is recorded exactly once even if
+  // teardown fails.
+  if (headersAlreadySent) {
+    terminateAfterHeadersSent(res, err, requestId);
+  }
 }
diff --git a/src/routes/proxyRoutes.ts b/src/routes/proxyRoutes.ts
index 6916059b..cafcf43d 100644
--- a/src/routes/proxyRoutes.ts
+++ b/src/routes/proxyRoutes.ts
@@ -268,6 +268,14 @@ export function createProxyRouter(deps: ProxyDeps): Router {
         res.status(upstreamStatus);
         if (upstreamRes.body) {
           const reader = upstreamRes.body.getReader();
+          // Release the upstream connection if the client goes away before the
+          // body has been fully delivered.
+          const onClientClose = (): void => {
+            if (!res.writableFinished) {
+              void reader.cancel().catch(() => undefined);
+            }
+          };
+          res.once('close', onClientClose);
           const pump = async (): Promise<void> => {
             while (true) {
               const { done, value } = await reader.read();
@@ -276,7 +284,18 @@ export function createProxyRouter(deps: ProxyDeps): Router {
             }
             res.end();
           };
-          await pump();
+          try {
+            await pump();
+          } catch (streamErr) {
+            // Mid-stream failure: headers are already flushed, so the error
+            // handler cannot send an envelope. Cancel the upstream body so its
+            // socket is freed; errorHandler then destroys the client response
+            // so the caller sees a terminated stream instead of a hang.
+            void reader.cancel(streamErr).catch(() => undefined);
+            throw streamErr;
+          } finally {
+            res.removeListener('close', onClientClose);
+          }
         } else {
           const text = await upstreamRes.text();
           res.send(text);