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Root cause: when ngrok dies externally (pkill, crash, timeout), the server still reports tunnelActive=true with a dead URL. pair-agent prints an instruction block pointing at a dead tunnel. The remote agent gets "endpoint offline" and the user has to manually restart everything. Three-layer fix: - Server /pair endpoint: probes tunnel URL before returning it. If dead, resets tunnelActive/tunnelUrl and returns null (triggers CLI restart). - Server /tunnel/start: probes cached tunnel before returning already_active. If dead, falls through to restart ngrok automatically. - CLI pair-agent: double-checks tunnel URL from server before printing instruction block. Falls through to auto-start on failure. 4 regression tests verify all three probe points + CLI verification. Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>