The Tailscale magic ✨ is starting to wear off. I gave positive opinions on Tailscale back in August 2022:
Basically Tailscale does one thing extremely well and the accompanying features aren’t bad either. The free tier suits me very well too!
Tailscale used to work flawlessly but as the features have expanded the issues are creeping in. I have multiple email conversations open trying to establish the cause of my issues. One issue — iOS unable to access subnet routes — was recently confirmed as a possible bug:
I spotted another report of this exact issue come in. It sounds like something indeed changed with the iOS behavior.
Tailscale Support
I am reluctant to call these issues “bugs” because I’m well aware that as a tinkerer of a self-hosted LAN network I may well be the problem. However, when the only change I’ve made is updating Tailscale, I’m inclined to point the finger.
Networking is complicated to say the least. There are many 3rd parties involved so stuff working 100% of the time would be a miracle — but that was the magic of Tailscale! It worked flawlessly for a long time.
Recently there was the containers issue; the result of a breaking change in v1.66. That change was reverted in v1.66.4. I still don’t fully understand the security issue that resulted in this flip-flopping. All I know is my setup was broken for two weeks. The side effect — “inadvertently broke DNS resolution from containers” — was presumably missed in testing. Not a great start. Then the U-turn by deciding it wasn’t a security concern after all makes the whole issue a farce. I shouldn’t be questioning whether or not to apply security updates.
Just Worked
I keep thinking of those early days with Tailscale where it “just worked”. Now I’m getting Dropbox vibes, which is disconcerting. Dropbox went from “just works” to literally failing to do the one thing it was designed to do. There was a time I would install Dropbox on every machine I could. Then the bugs and bloat crept in. Dropbox pivoted to who-knows-what and the primary feature stopped working. I uninstalled Dropbox everywhere and deleted my account.
Tailscale is a long way from Dropbox levels of failure but the magic is wearing off. I’m still optimistic about Tailscale though. Bugs are fixed and the technical support is exceptional. Even free-tier email support has technical nous. They are keen to get issues fixed. Let’s hope this continues.
If Tailscale does go full-Dropbox there is plenty of competition in ZeroTier, etc. Tailscale even has a handy Tailscale vs. alternatives page. That comparison page is basically a canary. If it 404s in future I’ll know it’s time to jump ship.
PS, if anyone else is getting latency spikes and intermittent freezes with Tailscale SSH on a local direct connection — please report it!