a hack i've been thinking of i also want to try someday.

When your instance goes down, you get annoying 500 errors, right. But what if you can set a retry in the http proxy and tell it to retry for several seconds. You could basically restart while it looks like you still have uptime, hehe (just bigger latency).

And a quick glance tells me something like that may be possible in Caddy by using the load balancers lb_try_duration and lb_try_interval. And yes, this is load balancing settings, but who's to say you can't have a load balancing setup with only one node :blobfoxcomfysmirk: