Problem
I wanted to test changing my login, but had a lot of difficulty figure out how to do so. Eventually I got it to happen by deleting tag:homeassistant in the Home Assistant Tailscale Configuration. I'm not sure why that triggered login and whether I had to do other steps as well, but at least I got it eventually. Since tag:homeassistant is the default per https://github.com/hassio-addons/app-tailscale/blob/main/tailscale/DOCS.md#configuration and thus presumably recommended, I added it back into the config and restarted the app before actually logging into my new tailnet -- but then I got the error described in #642, so I disabled it again.
Taildrop is only supported between devices in the same tailnet, which is one reason why I do not want to simply share the existing device with a new tailnet. Another reason is I do not want to continue managing two different tailnets, so I want all devices migrated to the new tailnet.
Attempt to log out using key expiry
From the Tailscale login console, I attempted reactivating key expiry for the homeassistant device. However while it initially showed expiry in 30 minutes, after that amount of time it jumped to expiration in 4 months. https://tailscale.com/docs/features/tags#key-expiry says "the device's key expiry will not change unless you re-authenticate", so perhaps this was messing with it somehow. In any case, using key expiry is still not ideal since the minimum setting is 1 day in Tailscale device management.
Attempt to log out using Web UI
As noted in #314, the Home Assistant Tailscale Web UI is read-only due to being an iframe, and as of recent versions http://<device's TS IP>:5252/ is completely disabled. This means I cannot manage my login there. Here is the Synology web UI showing logging in for read-write access, then going to details page for logout button:

Attempt to log out by changing login server configuration
In the Home Assistant Tailscale config, I attempted changing the Login server setting to https://controlplane.tailscale.commmm to hopefully force reauth. However after restarting the app, this prevented Tailscale from booting with error can't change --login-server without --force-reauth.
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App: Tailscale
Zero config VPN for building secure networks
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App version: 0.27.1
You are running the latest version of this app.
System: Home Assistant OS 17.1 (amd64 / qemux86-64)
Home Assistant Core: 2026.3.1
Home Assistant Supervisor: 2026.02.3
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can't change --login-server without --force-reauth
[15:43:41] FATAL: Unable to start up Tailscale
s6-rc: warning: unable to start service post-tailscaled: command exited 1
/run/s6/basedir/scripts/rc.init: warning: s6-rc failed to properly bring all the services up! Check your logs (in /run/uncaught-logs/current if you have in-container logging) for more information.
/run/s6/basedir/scripts/rc.init: fatal: stopping the container.
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Attempt to log out with --force-reauth
I tried figuring out how to send the --force-reauth flag via SSH or otherwise, and found #546 and #594 showing it requires additional experience tunneling into the Tailscale container versus just the regular Home Assistant container. So I gave up on this method after reading that ticket.
Problem
I wanted to test changing my login, but had a lot of difficulty figure out how to do so. Eventually I got it to happen by deleting
tag:homeassistantin the Home Assistant Tailscale Configuration. I'm not sure why that triggered login and whether I had to do other steps as well, but at least I got it eventually. Sincetag:homeassistantis the default per https://github.com/hassio-addons/app-tailscale/blob/main/tailscale/DOCS.md#configuration and thus presumably recommended, I added it back into the config and restarted the app before actually logging into my new tailnet -- but then I got the error described in #642, so I disabled it again.Taildrop is only supported between devices in the same tailnet, which is one reason why I do not want to simply share the existing device with a new tailnet. Another reason is I do not want to continue managing two different tailnets, so I want all devices migrated to the new tailnet.
Attempt to log out using key expiry
From the Tailscale login console, I attempted reactivating key expiry for the
homeassistantdevice. However while it initially showed expiry in 30 minutes, after that amount of time it jumped to expiration in 4 months. https://tailscale.com/docs/features/tags#key-expiry says "the device's key expiry will not change unless you re-authenticate", so perhaps this was messing with it somehow. In any case, using key expiry is still not ideal since the minimum setting is 1 day in Tailscale device management.Attempt to log out using Web UI
As noted in #314, the Home Assistant Tailscale Web UI is read-only due to being an iframe, and as of recent versions
http://<device's TS IP>:5252/is completely disabled. This means I cannot manage my login there. Here is the Synology web UI showing logging in for read-write access, then going to details page for logout button:Attempt to log out by changing login server configuration
In the Home Assistant Tailscale config, I attempted changing the
Login serversetting tohttps://controlplane.tailscale.commmmto hopefully force reauth. However after restarting the app, this prevented Tailscale from booting with errorcan't change --login-server without --force-reauth.Attempt to log out with
--force-reauthI tried figuring out how to send the --force-reauth flag via SSH or otherwise, and found #546 and #594 showing it requires additional experience tunneling into the Tailscale container versus just the regular Home Assistant container. So I gave up on this method after reading that ticket.