iOS connection does not restart


In the following scenario the only way to reconnect to an endpoint is to swipe-kill the iOS app and restart it.

Basically I connect via Tailscale to my NAS. Then in order to connect to another VPN I have to stop tailscale (make it inactive) and I connect via PIA. After exiting my PIA connection if I re-enable the tailscale connection via the app, the connection does not come up and I cannot ping the endpoint. I have to kill and restart the app and then the connection works.

This is true even if I never make the connection inactive and just connect to a second VPN

Is it that iOS doesn’t allow you to be connected to two VPNs at the same time?

No. The issue is not that I cannot connect to two VPNs at the same time - as I know that is a limitation of the iOS VPN service.

The issue is that switching away from tailscale to a different connection and disabling tailscale does not allow for tailscale to be re-enabled without restarting the iOS app. The active/disable switch no longer works in this scenario.

Hi @narensankar,
I wonder if you can recreate this and let us know the specific steps.
Would you also let us know the specific Tailscale IP address/ time of incident?

Start Tailscale app - make sure the switch is active.
ping to node on the network
It works.
Then switch app to stopped mode.
Go to iOS VPN settings and enable some other VPN connection. In my example I use PIA.
Connected to PIA VPN, so ping to node on Tailscale network will fail
Now disconnect from other VPN
Switch to Tailscale app and re-enable network
Network will not change to Active and the connection will fail.
If you kill and restart the tailscale app - Then the connection will be allowed to switch from Stopped to Active and ping will work again.

my node is at and I just tried it at around 8:52 am NYC time on Nov 18th.

Hi @narensankar
Any hints in the logs? Can you post them? Thanks!