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 I've recently started experimenting with holesail and setup a forward proxy to expose self-hosted holesail services to the broader internet.

Have you experienced issues when you stop the holesail server then try to restart it? I'm using holesail-manager, and when I stop the server then restart, I am unable to connect from the client until I make a new server session. Seems like it creates a new connection string...

Where is the best place to stay up to date on development? 
 this may be my problem... from the docs: "Note: If you did not set a custom connection string, stopping and restarting a session will reset it's connection string."
Do you have any content around how you manage your holesail connections? 
 You can setup a custom connection string to avoid that, holesail --live <port> --connector "any random stuff that is secure"

Future version will have a --preserve flag to keep the connection string same when the server restarts. 
 As @supersu said, this is purely a consequence of persistence not yet built in across sessions. The manager for multiple connections itself is actually only like a couple weeks old 😆

This is all pretty brand new, so expect updates that keep making it better. I’ll keep doing what I can to push it along as well. I know lots of people who are working to make this all much easier and more ubiquitous. I think there will be a point in the coming year where enough has finally reached a stable production level that this starts to proliferate really quickly. Then comes the time where we can easily connect any and all of our devices together for any reason, and it seems weird that it didn’t just always work like this.