Keeping Tailscale alive in OpenAI's Dots cloud computer: lessons and an open-source recovery script
CH_CGV · reddit · 2026-10-21
Reddit user CHCGV uses OpenAI's Dots cloud computer as a dev environment and shares hard-won lessons on keeping Tailscale connected: the hard part isn't connecting once, it's surviving environment restarts. His open-source dots-tailscale project keeps install files, Tailscale state, and SSH setup under /workspace, so one command (bash /workspace/.dots-tailscale/start.sh) restores the connection without re-login, using Tailscale userspace mode via relays. Verified scenarios include recovery after fresh boot with host-key verification, updates preserving node identity, rollback on failed updates, and a watchdog reviving SSH within a live environment. Key limitation: after an environment is replaced, recovery still requires manually running the command in the Dots terminal — the watchdog can't resurrect itself — and /workspace records shouldn't be trusted as a guaranteed backup.
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