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Deploy Fly.io Proxy / deploy (push) Successful in 34s
Bluegreen kept timing out — the new green machine couldn't reach "started" within Fly's 5-minute deploy budget. The cold-start sequence (tailscaled → tailscale up → wait-for-MagicDNS → nginx startup) eats most of that, leaving no headroom for healthcheck propagation. For a single-machine proxy, bluegreen offers little benefit anyway: no warm second instance, so trading 5-10s of downtime for predictable completion is the right call.
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Switch the Fly proxy deploy strategy from bluegreen to immediate in fly/fly.toml. With a single proxy machine, bluegreen offers little benefit — the green machine routinely failed to reach "started" inside Fly's default 5-minute deploy timeout (the cold-start sequence of tailscaled → tailscale up → wait-for-MagicDNS → nginx startup eats most of the budget), and the failed deploys would roll back. immediate replaces the machine in place with a brief downtime (~5–10s) but actually completes.