After macOS login, I have to manually log in to Tailscale

Tailscale version: Version 1.40.0 (App Store)
Your operating system & version: macOS Ventura (13.4)

I am using Tailscale on a few macOS machines, and every time they restart, Tailscale appears in the menu with an exclamation mark and the message “Please log in” (see screenshot).Tapping on “Log In…” automatically logs me in, I don’t need to go through any OAuth flow or anything.

Is there any way to fix this, so I am automatically logged in each time? When I search for solutions, I find a lot of things about switching to a system daemon so that you can start Tailscale before a user logs in. I don’t feel like this is my problem, because I have these machines setup to automatically login to a user on startup. It feels like this is a Tailscale issue, that it’s requiring me to press this menu bar item to login, even though it clearly doesn’t actually need me to enter my username/password again.

This happens consistently on 3 different macOS machines.

CleanShot 2023-05-19 at 08.48.40@2x