Hey @kentcdodds - That error generally indicates an issue with your local wireguard agent. Can you try the following:
Reset your wireguard connection using fly wireguard reset
Restart the flyctl agent with fly agent restart (or fly agent stop and fly agent start)
If you’re still seeing issues after the above, setting the the wireguard connection to use websockets with fly wireguard websockets enable may also help.
We had a bug with v0.1.28 where any command that relied on user mode wg would fail when the wire_guard_websockets key was missing from ~/.fly/config.yml. We reverted the change that caused this and are releasing v0.1.29 shortly with the fix.
The issue can be mitigated with v0.1.28 by calling fly wg websocket disable or fly wg websocket enable—both will set the wire_guard_websockets key in ~/.fly/config.yml`.