diff --git a/.env.example b/.env.example
index 4726805b..97e8dba8 100644
--- a/.env.example
+++ b/.env.example
@@ -142,6 +142,13 @@ MCP_DOCMOST_PASSWORD=
 # provider is eventually broken instead of leaking forever. Default 900000 (15 min).
 # AI_STREAM_TIMEOUT_MS=900000
 
+# Keep-alive recycle window (ms) for streaming chat/agent AI + external-MCP calls.
+# A pooled connection idle longer than this is closed instead of reused, so a
+# NAT / egress firewall / reverse proxy that silently drops idle connections
+# cannot poison a reused socket into a PRE-RESPONSE `read ECONNRESET`. Lower it if
+# your egress drops idle connections faster than ~10s. Default 10000 (10 s).
+# AI_STREAM_KEEPALIVE_MS=10000
+
 # --- Anonymous public-share AI assistant ---
 # Opt-in per workspace (AI settings -> "public share assistant"; off by default).
 # When enabled, anonymous visitors of a published share can ask an AI about that
diff --git a/apps/server/src/integrations/ai/ai-streaming-fetch.spec.ts b/apps/server/src/integrations/ai/ai-streaming-fetch.spec.ts
index b28ecf51..07c8ec40 100644
--- a/apps/server/src/integrations/ai/ai-streaming-fetch.spec.ts
+++ b/apps/server/src/integrations/ai/ai-streaming-fetch.spec.ts
@@ -1,8 +1,11 @@
 import * as http from 'node:http';
 import {
   createStreamingFetch,
+  withPreResponseRetry,
   streamTimeoutMs,
+  streamKeepAliveMs,
   streamingDispatcherOptions,
+  isRetryableConnectError,
 } from './ai-streaming-fetch';
 
 /**
@@ -38,15 +41,54 @@ describe('streamTimeoutMs', () => {
     }
   });
 
-  it('applies the timeout to BOTH undici stream timeouts', () => {
+  it('applies the silence timeout + keep-alive recycle window to the dispatcher', () => {
     delete process.env.AI_STREAM_TIMEOUT_MS;
+    delete process.env.AI_STREAM_KEEPALIVE_MS;
     expect(streamingDispatcherOptions()).toEqual({
       headersTimeout: 900_000,
       bodyTimeout: 900_000,
+      keepAliveTimeout: 10_000,
+      keepAliveMaxTimeout: 10_000,
     });
   });
 });
 
+describe('streamKeepAliveMs', () => {
+  const ORIG = process.env.AI_STREAM_KEEPALIVE_MS;
+  afterEach(() => {
+    if (ORIG === undefined) delete process.env.AI_STREAM_KEEPALIVE_MS;
+    else process.env.AI_STREAM_KEEPALIVE_MS = ORIG;
+  });
+
+  it('defaults to 10s (recycle idle sockets so a NAT/proxy drop cannot poison reuse)', () => {
+    delete process.env.AI_STREAM_KEEPALIVE_MS;
+    expect(streamKeepAliveMs()).toBe(10_000);
+  });
+
+  it('honours a positive override and ignores invalid/non-positive', () => {
+    process.env.AI_STREAM_KEEPALIVE_MS = '4000';
+    expect(streamKeepAliveMs()).toBe(4000);
+    for (const bad of ['0', '-1', 'x', '']) {
+      process.env.AI_STREAM_KEEPALIVE_MS = bad;
+      expect(streamKeepAliveMs()).toBe(10_000);
+    }
+  });
+});
+
+describe('isRetryableConnectError', () => {
+  it('matches connection-level codes on the error or its cause', () => {
+    expect(isRetryableConnectError({ cause: { code: 'ECONNRESET' } })).toBe(true);
+    expect(isRetryableConnectError({ cause: { code: 'UND_ERR_SOCKET' } })).toBe(true);
+    expect(isRetryableConnectError({ code: 'ECONNREFUSED' })).toBe(true);
+  });
+  it('does NOT match aborts / unrelated errors', () => {
+    expect(isRetryableConnectError({ name: 'AbortError', cause: { code: 'ABORT_ERR' } })).toBe(false);
+    expect(isRetryableConnectError({ cause: { code: 'UND_ERR_HEADERS_TIMEOUT' } })).toBe(false);
+    expect(isRetryableConnectError(new Error('plain'))).toBe(false);
+    expect(isRetryableConnectError(undefined)).toBe(false);
+  });
+});
+
 describe('createStreamingFetch — against a delayed server', () => {
   const ORIG = process.env.AI_STREAM_TIMEOUT_MS;
   let server: http.Server;
@@ -110,3 +152,84 @@ describe('createStreamingFetch — against a delayed server', () => {
     if (code) expect(code).toBe('UND_ERR_HEADERS_TIMEOUT');
   });
 });
+
+describe('withPreResponseRetry', () => {
+  // The retry is the OUTERMOST layer (over the dispatcher-bound streaming fetch),
+  // matching ai.service's withPreResponseRetry(instrument(createStreamingFetch())).
+  // PRE_RESPONSE_CONNECT_RETRIES is 2 -> at most 3 total attempts.
+  const MAX_ATTEMPTS = 3;
+  let server: http.Server;
+  let url: string;
+  let requests = 0;
+  // 'first' resets only the first connection; 'all' resets every connection.
+  let resetMode: 'first' | 'all' = 'first';
+
+  const retryingFetch = () => withPreResponseRetry(createStreamingFetch());
+
+  beforeAll(async () => {
+    server = http.createServer((req, res) => {
+      requests += 1;
+      const shouldReset = resetMode === 'all' || requests === 1;
+      if (shouldReset) {
+        // Reset before any response byte (a poisoned/stale keep-alive socket).
+        const sock = req.socket as import('node:net').Socket & {
+          resetAndDestroy?: () => void;
+        };
+        if (typeof sock.resetAndDestroy === 'function') sock.resetAndDestroy();
+        else sock.destroy();
+        return;
+      }
+      res.writeHead(200, { 'Content-Type': 'text/plain' });
+      res.end('ok');
+    });
+    await new Promise<void>((resolve) => server.listen(0, '127.0.0.1', resolve));
+    const addr = server.address() as import('node:net').AddressInfo;
+    url = `http://127.0.0.1:${addr.port}/`;
+  });
+
+  afterAll(async () => {
+    await new Promise<void>((resolve) => server.close(() => resolve()));
+  });
+
+  beforeEach(() => {
+    requests = 0;
+    resetMode = 'first';
+  });
+
+  it('retries a pre-response reset on a fresh connection and succeeds', async () => {
+    resetMode = 'first';
+    const res = await retryingFetch()(url);
+    expect(res.status).toBe(200);
+    expect(await res.text()).toBe('ok');
+    // first request reset -> retry -> second request served.
+    expect(requests).toBe(2);
+  });
+
+  it('gives up after the retry bound and rethrows the original reset', async () => {
+    resetMode = 'all'; // every attempt resets -> retries exhaust
+    let caught: unknown;
+    try {
+      await retryingFetch()(url);
+    } catch (e) {
+      caught = e;
+    }
+    expect(caught).toBeDefined();
+    // A retryable connection error reached the caller (not swallowed).
+    expect(isRetryableConnectError(caught)).toBe(true);
+    // Bounded: exactly PRE_RESPONSE_CONNECT_RETRIES + 1 attempts hit the server
+    // (pins both the limit and that the final error propagates — guards an
+    // off-by-one or an infinite loop).
+    expect(requests).toBe(MAX_ATTEMPTS);
+  });
+
+  it('does NOT retry an aborted request (no retry storm)', async () => {
+    resetMode = 'all';
+    const ctrl = new AbortController();
+    ctrl.abort();
+    await expect(
+      retryingFetch()(url, { signal: ctrl.signal }),
+    ).rejects.toBeDefined();
+    // Pre-aborted: the request never reached the server, so nothing was retried.
+    expect(requests).toBe(0);
+  });
+});
diff --git a/apps/server/src/integrations/ai/ai-streaming-fetch.ts b/apps/server/src/integrations/ai/ai-streaming-fetch.ts
index f257fe4e..b781df9a 100644
--- a/apps/server/src/integrations/ai/ai-streaming-fetch.ts
+++ b/apps/server/src/integrations/ai/ai-streaming-fetch.ts
@@ -18,41 +18,139 @@ import { Agent } from 'undici';
  */
 const DEFAULT_STREAM_TIMEOUT_MS = 900_000;
 
+/**
+ * Default keep-alive recycle window (10s). A pooled connection idle longer than
+ * this is CLOSED rather than reused.
+ *
+ * Long agent turns leave gaps of tens of seconds between provider calls (one
+ * call per step; a crawl/search tool runs in between). A NAT / reverse proxy /
+ * conntrack in front of the deployment silently drops an idle connection after
+ * its own timeout; undici, not knowing, then reuses that dead socket and the
+ * next request fails PRE-RESPONSE with `read ECONNRESET` (#175 prod telemetry:
+ * the resets correlate with idleSincePrevCall ~42s, while a direct path to the
+ * provider does NOT reset). Recycling idle sockets well below such a drop window
+ * means a long-gap call opens a fresh connection instead of reusing a stale one.
+ * `keepAliveMaxTimeout` also caps a server-advertised keep-alive so the provider
+ * cannot push the reuse window back up.
+ */
+const DEFAULT_STREAM_KEEPALIVE_MS = 10_000;
+
+/**
+ * How many times to retry a PRE-RESPONSE connection failure (a reset/timeout
+ * before ANY response byte) on a fresh connection. Safe because `fetch()` only
+ * rejects before the Response resolves — a started stream is never replayed.
+ */
+const PRE_RESPONSE_CONNECT_RETRIES = 2;
+
+/** undici cause codes for a connection-level failure that occurred PRE-RESPONSE. */
+const RETRYABLE_CONNECT_CODES = new Set([
+  'ECONNRESET',
+  'ECONNREFUSED',
+  'EPIPE',
+  'ETIMEDOUT',
+  'UND_ERR_SOCKET',
+  'UND_ERR_CONNECT_TIMEOUT',
+]);
+
+function positiveEnv(name: string, fallback: number): number {
+  const raw = Number(process.env[name]);
+  return Number.isFinite(raw) && raw > 0 ? raw : fallback;
+}
+
 /**
  * The configured silence timeout (ms). Override with `AI_STREAM_TIMEOUT_MS`; a
  * missing/invalid/non-positive value falls back to {@link DEFAULT_STREAM_TIMEOUT_MS}.
  */
 export function streamTimeoutMs(): number {
-  const raw = Number(process.env.AI_STREAM_TIMEOUT_MS);
-  return Number.isFinite(raw) && raw > 0 ? raw : DEFAULT_STREAM_TIMEOUT_MS;
+  return positiveEnv('AI_STREAM_TIMEOUT_MS', DEFAULT_STREAM_TIMEOUT_MS);
+}
+
+/** Keep-alive recycle window (ms). Override with `AI_STREAM_KEEPALIVE_MS`. */
+export function streamKeepAliveMs(): number {
+  return positiveEnv('AI_STREAM_KEEPALIVE_MS', DEFAULT_STREAM_KEEPALIVE_MS);
 }
 
 /**
- * undici `Agent` timeout options for streaming AI traffic — both stream timeouts
- * set to the (generous, finite) silence timeout. Shared by the chat provider
- * fetch and the external-MCP dispatcher so they behave identically (#175).
+ * undici `Agent` options for streaming AI traffic — the (generous, finite)
+ * silence timeouts plus the keep-alive recycle window. Shared by the chat
+ * provider fetch and the external-MCP dispatcher so they behave identically.
  */
 export function streamingDispatcherOptions(): {
   headersTimeout: number;
   bodyTimeout: number;
+  keepAliveTimeout: number;
+  keepAliveMaxTimeout: number;
 } {
   const t = streamTimeoutMs();
-  return { headersTimeout: t, bodyTimeout: t };
+  const ka = streamKeepAliveMs();
+  return {
+    headersTimeout: t,
+    bodyTimeout: t,
+    keepAliveTimeout: ka,
+    keepAliveMaxTimeout: ka,
+  };
+}
+
+/** True for a connection-level error worth retrying on a fresh connection. */
+export function isRetryableConnectError(err: unknown): boolean {
+  const e = err as { code?: string; cause?: { code?: string } } | undefined;
+  const code = e?.cause?.code ?? e?.code;
+  return typeof code === 'string' && RETRYABLE_CONNECT_CODES.has(code);
 }
 
 /**
  * Build a `fetch` for long-lived streaming AI calls (the agent chat turn) backed
- * by a dedicated undici dispatcher whose stream timeouts are the generous-but-
- * finite silence timeout above (#175). A single shared dispatcher is returned
- * (callers hold it for the service lifetime) so its connection pool is reused.
+ * by a dedicated undici dispatcher (finite silence timeouts + keep-alive
+ * recycling, #175). A single shared dispatcher is returned (callers hold it for
+ * the service lifetime) so its connection pool is reused.
+ *
+ * This is the BASE transport — no retry. The chat path wraps it as
+ * `withPreResponseRetry(createInstrumentedFetch(ctx, createStreamingFetch()))`
+ * so the retry is the OUTERMOST layer and the instrumentation observes EVERY
+ * attempt (a recovered reset is still logged — see withPreResponseRetry).
  */
 export function createStreamingFetch(): typeof fetch {
   const dispatcher = new Agent(streamingDispatcherOptions());
   return ((input: Parameters<typeof fetch>[0], init?: RequestInit) =>
     fetch(input, {
       ...(init ?? {}),
-      // `dispatcher` is an undici-specific init field (not in the DOM RequestInit
-      // type); Node's global fetch reads it. Cast to satisfy the type.
+      // `dispatcher` is an undici-specific init field (not in the DOM
+      // RequestInit type); Node's global fetch reads it. Cast to satisfy it.
       dispatcher,
     } as RequestInit & { dispatcher: Agent })) as typeof fetch;
 }
+
+/**
+ * Wrap a fetch so a PRE-RESPONSE connection reset (`baseFetch` rejects before the
+ * Response resolves — so nothing has streamed) is retried a few times on a fresh
+ * connection (#175). A poisoned keep-alive socket is destroyed by undici on the
+ * reset, so the retry lands on a new connection. An abort (client disconnect) is
+ * never retried.
+ *
+ * This is the OUTERMOST transport layer by design: composing it as
+ * `withPreResponseRetry(instrumentedFetch)` means every attempt — including the
+ * resets that the retry recovers from — flows through the instrumentation, so the
+ * "PRE-RESPONSE FAILED ... ECONNRESET ... idleSincePrevCall" telemetry stays
+ * visible precisely when the fix is working (and AI_STREAM_KEEPALIVE_MS can be
+ * tuned from real data). A retry INSIDE the transport would hide it.
+ */
+export function withPreResponseRetry(baseFetch: typeof fetch): typeof fetch {
+  return (async (input: Parameters<typeof fetch>[0], init?: RequestInit) => {
+    for (let attempt = 0; ; attempt++) {
+      try {
+        return await baseFetch(input, init);
+      } catch (err) {
+        const aborted = init?.signal?.aborted === true;
+        if (
+          aborted ||
+          attempt >= PRE_RESPONSE_CONNECT_RETRIES ||
+          !isRetryableConnectError(err)
+        ) {
+          throw err;
+        }
+        // Brief backoff before the fresh-connection retry.
+        await new Promise((resolve) => setTimeout(resolve, 150 * (attempt + 1)));
+      }
+    }
+  }) as typeof fetch;
+}
diff --git a/apps/server/src/integrations/ai/ai.service.ts b/apps/server/src/integrations/ai/ai.service.ts
index 18f15b5d..16aa6997 100644
--- a/apps/server/src/integrations/ai/ai.service.ts
+++ b/apps/server/src/integrations/ai/ai.service.ts
@@ -16,7 +16,10 @@ import { AiEmbeddingNotConfiguredException } from './ai-embedding-not-configured
 import { AiSttNotConfiguredException } from './ai-stt-not-configured.exception';
 import { describeProviderError } from './ai-error.util';
 import { createInstrumentedFetch } from './ai-provider-http';
-import { createStreamingFetch } from './ai-streaming-fetch';
+import {
+  createStreamingFetch,
+  withPreResponseRetry,
+} from './ai-streaming-fetch';
 import { AiProviderCredentialsRepo } from '@docmost/db/repos/ai-chat/ai-provider-credentials.repo';
 import { SecretBoxService } from '../crypto/secret-box';
 import { AiDriver } from './ai.types';
@@ -46,14 +49,15 @@ export interface ChatModelOverride {
 export class AiService {
   private readonly logger = new Logger(AiService.name);
 
-  // Provider HTTP fetch for the chat path: the streaming fetch — which RAISES
-  // undici's 300s headers/body timeouts to a generous-but-finite silence timeout
-  // so a long agent turn is not severed mid-stream (#175) — wrapped with the
-  // provider-HTTP instrumentation so the logs observe that exact transport. Held
-  // for the service lifetime to reuse the streaming dispatcher's connection pool.
-  private readonly aiProviderFetch = createInstrumentedFetch(
-    'AiService:provider-http',
-    createStreamingFetch(),
+  // Provider HTTP fetch for the chat path, layered so each transport concern is
+  // observed (#175). Inside-out: the streaming fetch (finite silence timeouts +
+  // keep-alive recycling) → provider-HTTP instrumentation (logs every attempt) →
+  // pre-response connection-reset retry as the OUTERMOST layer. Retry-outer means
+  // a reset the retry recovers from is still logged with its idle-gap, instead of
+  // collapsing into a clean "OK". Held for the service lifetime to reuse the
+  // streaming dispatcher's connection pool.
+  private readonly aiProviderFetch = withPreResponseRetry(
+    createInstrumentedFetch('AiService:provider-http', createStreamingFetch()),
   );
 
   constructor(