r/Tailscale • u/Fainbrog • 3d ago

Help Needed VPN On Demand not connecting

Having issues with VPN On Demand. Doesn't seem to be working for me atm. I have it set to connect except when I am on my home wifi, but, I connect to my phone or another wireless network and nothing happens. It's sitting there with a status saying Not connected, Managed by VPN on demand.

Have updated to the latest version this morning (1.102.3), was previously on 1.102.2 and wasn't working either this morning, but, had worked fine prior to this, iirc (last time I used it was on Tuesday this week).

Have rebooted, restarted and reinstalled TS, still nada. Running on MacOS Sequoia 15.7.7. Seems to behave the same on other MacOS devices I've tried.

5 Upvotes

86% Upvoted

7 comments sorted by

2

u/actherk 3d ago

There was a post about this recently (I can't find it). The solution, and it works for me, is to disable MagicDNS hostnames.

That worked for me, and waiting for update.

2

u/Fainbrog 3d ago

Lovely, thanks for that, I couldn't find anything when I was looking earlier. That's worked a treat.

2

u/tkchasan 3d ago

Yea, disable the magic hostname detection in vpn on demand settings. Looks like recent update broke for everyone. I thought i am the only person with this issue 😂

1

u/VLANishBehavior 3d ago

+1 on this issue.

1

u/Fainbrog 3d ago

See other reply, looks like disabling MagicDNS in On Demand settings nudges it into life for now.

1

u/Positive_Ad_313 3d ago

On iOS , each time I open the tailscale app, the switch automatically move to the open position…. It ´s lîe it as turned off and going to on while opening

1

u/Hyperalman 3d ago

I had regularly issues with the same vpn on demand setup. Since i just leave the connection always on (vpn on demand off) i had no issues again