diff --git a/src/servers/sidecar/claude/claude-manager.ts b/src/servers/sidecar/claude/claude-manager.ts
index 155c2dfa..232b17b6 100644
--- a/src/servers/sidecar/claude/claude-manager.ts
+++ b/src/servers/sidecar/claude/claude-manager.ts
@@ -1,3 +1,5 @@
+import { existsSync } from 'node:fs';
+import { homedir } from 'node:os';
 import { join } from 'node:path';
 import { query, type Query } from '@anthropic-ai/claude-agent-sdk';
 import type { ChatEvent } from '../../api/chat/types';
@@ -7,9 +9,27 @@ import { createParseState, processMessage } from './stream-parser';
 
 const SEND_TIMEOUT_MS = 30 * 60 * 1000;
 
-// Use /usr/local/bin/claude so it's visible inside bwrap sandbox (which ro-binds /usr).
-// The actual binary lives at ~/.local/bin/claude, symlinked from /usr/local/bin/claude.
-const CLAUDE_BIN = '/usr/local/bin/claude';
+// Where the Claude Code CLI lives. This was hardcoded to /usr/local/bin/claude, which dated from the
+// bwrap-sandboxed architecture: the jail ro-bound /usr and saw nothing else, so the installer's real
+// target (~/.local/bin/claude) had to be symlinked into a path the sandbox could reach. That sandbox
+// is gone, and the hardcoded path made the sidecar unrunnable anywhere it does not exist — a stock
+// macOS host has no /usr/local/bin at all.
+//
+// Resolution order mirrors OPENCODE_BIN in the opencode sidecar: an explicit pin, then PATH, then the
+// locations Anthropic's installer actually writes to.
+function resolveClaudeBin(): string {
+  const pinned = process.env.CLAUDE_BIN;
+  if (pinned) return pinned;
+
+  const onPath = Bun.which('claude');
+  if (onPath) return onPath;
+
+  const candidates = [join(homedir(), '.local', 'bin', 'claude'), '/usr/local/bin/claude', '/opt/homebrew/bin/claude'];
+  return candidates.find((candidate) => existsSync(candidate)) ?? 'claude';
+}
+
+const CLAUDE_BIN = resolveClaudeBin();
+console.log(`[claude] CLI resolved to ${CLAUDE_BIN}`);
 
 // Capture original HOME before user-instance overrides it
 const HOST_HOME = process.env.HOME!;