Literally nothing looks wrong in caddy's access and error logs, mastodon-web, or mastodon-streaming. I see the request for /api/v1/instance when my bot's reply script starts and then one for /api/v1/streaming/user when it times out. All with a 200 response.
@izaliamae does caddy support websocket proxying?
@ben Yep. I need to do some more poking around though because I'm only getting websocket errors on this account. The other 3 are fine.