diff --git a/docs/chat-chain-changes/2026-10-22-bridge-bootstrap-before-ready.md b/docs/chat-chain-changes/2026-10-22-bridge-bootstrap-before-ready.md
new file mode 100644
index 0000000..6ee493d
--- /dev/null
+++ b/docs/chat-chain-changes/2026-10-22-bridge-bootstrap-before-ready.md
@@ -0,0 +1,19 @@
+---
+date: 2026-10-22
+feature: Agent Bridge startup
+impact: Prevent first-turn connection loss during Hermes interpreter relaunch
+commit: pending
+---
+# Initialize Hermes before Bridge readiness
+
+- Commit: pending local validation.
+- Feature: Agent Bridge process startup, first chat/context estimate.
+- Cause: importing run_agent after the worker socket was ready invoked Hermes bootstrap, which execed from the selected dependency venv into managed Python and dropped the in-flight request.
+- Change: run Hermes bootstrap in the manager launch command before starting the broker. Workers inherit the selected interpreter; vendored Python and Socket.IO contracts remain unchanged.
+- Validation: focused manager and bridge tests, cold-worker context estimates and first chat, production build.
+
+## Results
+- Harness and full production build passed.
+- Focused manager/concurrency suite: 54 passed; two pre-existing no-source tests also fail unchanged on this host because a global Hermes checkout exists.
+- Cold magic-conch and snowy-owl context estimates succeeded; the first snowy-owl chat completed with OK.
+- Focused browser chat streaming test passed with one worker. Broad parallel browser run: 3 passed, 8 input-locator failures; no client code changed.
diff --git a/packages/server/src/services/hermes/agent-bridge/manager.ts b/packages/server/src/services/hermes/agent-bridge/manager.ts
index f8c056d..bd63ec4 100644
--- a/packages/server/src/services/hermes/agent-bridge/manager.ts
+++ b/packages/server/src/services/hermes/agent-bridge/manager.ts
@@ -312,6 +312,24 @@ export function resolveAgentBridgeCommand(options: AgentBridgeManagerOptions = {
   return { command: fallback, argsPrefix: [], agentRoot, hermesHome }
 }
 
+export function buildAgentBridgeLaunchArgs(command: BridgeCommand, script: string): string[] {
+  const root = command.agentRoot
+  if (!root || !existsSync(join(root, 'hermes_bootstrap.py'))) {
+    return [...command.argsPrefix, script]
+  }
+  // Bootstrap may exec into Hermes's managed Python. Do that before the broker
+  // forks workers or opens sockets, so the first request survives initialization.
+  // Keep sys.argv[0] as -c until bootstrap returns so its relaunch replays this code.
+  const bootstrap = [
+    'import sys, runpy',
+    'sys.path.insert(0, ' + JSON.stringify(root) + ')',
+    'import hermes_bootstrap',
+    'sys.argv = sys.argv[1:]',
+    "runpy.run_path(sys.argv[0], run_name='__main__')",
+  ].join('; ')
+  return [...command.argsPrefix, '-c', bootstrap, script]
+}
+
 function bridgeScriptPath(): string {
   const candidates = [
     // Built server: dist/server/index.js -> dist/server/agent-bridge/python/hermes_bridge.py
@@ -922,7 +940,7 @@ export class AgentBridgeManager {
     const script = bridgeScriptPath()
     const command = resolveAgentBridgeCommand(this.options)
     await this.prepareEndpoint()
-    const args = [...command.argsPrefix, script, '--endpoint', this.endpoint]
+    const args = [...buildAgentBridgeLaunchArgs(command, script), '--endpoint', this.endpoint]
     const agentRoot = command.agentRoot
     const hermesHome = command.hermesHome
     if (agentRoot) args.push('--agent-root', agentRoot)
diff --git a/tests/server/agent-bridge-manager.test.ts b/tests/server/agent-bridge-manager.test.ts
index 1288504..e5d2316 100644
--- a/tests/server/agent-bridge-manager.test.ts
+++ b/tests/server/agent-bridge-manager.test.ts
@@ -1,3 +1,4 @@
+import { execFileSync } from 'child_process'
 import { EventEmitter } from 'events'
 import { chmodSync, mkdirSync, mkdtempSync, rmSync, writeFileSync } from 'fs'
 import { createServer, type Server } from 'net'
@@ -113,6 +114,35 @@ describe('agent bridge manager command resolution', () => {
     })
   })
 
+  it('bootstraps before the bridge starts even when bootstrap replaces the interpreter', async () => {
+    const root = join(tempDir, 'agent root')
+    const script = join(tempDir, 'bridge.py')
+    mkdirSync(root, { recursive: true })
+    writeFileSync(join(root, 'hermes_bootstrap.py'), [
+      'import os, sys',
+      "if os.environ.get('TEST_BRIDGE_BOOTSTRAPPED') != 'yes':",
+      "    os.environ['TEST_BRIDGE_BOOTSTRAPPED'] = 'yes'",
+      '    os.execv(sys.executable, [sys.executable, *sys.orig_argv[1:]])',
+    ].join('\n'))
+    writeFileSync(script, [
+      'import json, os, sys',
+      "assert os.environ.get('TEST_BRIDGE_BOOTSTRAPPED') == 'yes'",
+      'print(json.dumps(sys.argv))',
+    ].join('\n'))
+    const { buildAgentBridgeLaunchArgs } = await import('../../packages/server/src/services/hermes/agent-bridge/manager')
+    const args = buildAgentBridgeLaunchArgs({ command: 'python3', argsPrefix: [], agentRoot: root, hermesHome: tempDir }, script)
+    const env = { ...process.env }
+    delete env.TEST_BRIDGE_BOOTSTRAPPED
+    const output = execFileSync(process.platform === 'win32' ? 'python' : 'python3', [...args, '--endpoint', 'ipc:///test.sock'], { env, encoding: 'utf8', timeout: 10000 })
+    expect(JSON.parse(output.trim())).toEqual([script, '--endpoint', 'ipc:///test.sock'])
+  })
+
+  it('preserves legacy launch arguments when Hermes has no bootstrap module', async () => {
+    const { buildAgentBridgeLaunchArgs } = await import('../../packages/server/src/services/hermes/agent-bridge/manager')
+    expect(buildAgentBridgeLaunchArgs({ command: 'uv', argsPrefix: ['run', 'python'], agentRoot: tempDir, hermesHome: tempDir }, 'bridge.py'))
+      .toEqual(['run', 'python', 'bridge.py'])
+  })
+
   it('injects Web UI OpenRouter attribution into the bridge process env by default', async () => {
     const { buildAgentBridgeProcessEnv } = await import('../../packages/server/src/services/hermes/agent-bridge/manager')
     const env = buildAgentBridgeProcessEnv('ipc:///tmp/test.sock', '/tmp/hermes-home', '/tmp/hermes-agent')