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 I’m going to be pressuring Start9 on this too, but right now I can do it manually without needing explicit integration. It would be really nice to have it though so I’m going to push for it over there too. 
 I'd like that (and contribute to a bounty) too.

Zeus connected to Start9 using Lightning Node Connect works ok-ish, but is still kinda slow and crashes a lot.
I've no idea how to install Tailscale on start9 to even try if it would work any better,
so some easy solution like direct integration in apps and a Start9 package (at least while there's no clearnet-support) would be much appreciated. 
 Here’s how to do it manually

nostr:nevent1qqsrjjfa6r0k5r2a2fpsk45st55hl0pvc04u94c0ggfrhy420lpwmpgzyqpkz2cwhtswerfsqvwygzaqslleh5tzjckllwjtdcppa3906ufpvcwmkhm 
 Thanks, I'll look into that later,
running LND though, can't make much of a difference, right? 
 Should be quite similar 
 The difference is the macaroon hex which you can get easily. Sorry i never pushed an official tailscale package for start9. Was told next version is coming soon and packaging would be easier so waiting... 
 I'm a newly minted Start9 runner. I bought a Server One from them in Nashville this year, nostr:nprofile1qqstnem9g6aqv3tw6vqaneftcj06frns56lj9q470gdww228vysz8hqpz4mhxue69uhk2er9dchxummnw3ezumrpdejqzrthwden5te0dehhxtnvdakqz9rhwden5te0wfjkccte9ejxzmt4wvhxjmcjgxv3n, and I'd be very grateful if you're able to motivate getting holesail and other Pear and related packages into the Start9 Marketplace ecosystem.🙏🏻😆💖 
 It’s happening. We are waiting on just a few things for the Start9 side to be done. They’ve just been working hard on the new mobile version, which they want to finish before launching on Start9 so it can be used out the gate. In other words, it’s basically done on the start9 side, but not releasing until theres a way to really make use of it 👏🏻 
 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. 
 It is in the works 👀