Tailscale on Windows not connecting and getting 169.254.0.0/16 IP

At some point over the last day or two one of my Windows laptops no longer seems to connect to Tailscale correctly. This started with Tailscale 1.4.4 and I’m still seeing it after upgrading to 1.4.5 and after several reboots and disconnect/reconnects in the taskbar menu.

Looking in the ipconfig /all output, I’m seeing this:

Unknown adapter Tailscale:

   Connection-specific DNS Suffix  . : [redacted].gmail.com.beta.tailscale.net
   Description . . . . . . . . . . . : Wintun Userspace Tunnel
   Physical Address. . . . . . . . . :
   DHCP Enabled. . . . . . . . . . . : No
   Autoconfiguration Enabled . . . . : Yes
   Link-local IPv6 Address . . . . . : fe80::[redacted]%12(Preferred)
   Autoconfiguration IPv4 Address. . : 169.254.83.107(Preferred)
   Subnet Mask . . . . . . . . . . . : 255.255.0.0
   Default Gateway . . . . . . . . . :
   DNS Servers . . . . . . . . . . . : 100.100.100.100
   NetBIOS over Tcpip. . . . . . . . : Enabled
   Connection-specific DNS Suffix Search List :
                                       [redacted].gmail.com.beta.tailscale.net

tailscale netcheck shows this:

> tailscale netcheck

Report:
        * UDP: true
        * IPv4: yes, [redacted]:52575
        * IPv6: no
        * MappingVariesByDestIP: false
        * HairPinning: false
        * PortMapping:
        * Nearest DERP: London
        * DERP latency:
                - lhr: 31ms    (London)
                - fra: 44ms    (Frankfurt)
                - nyc: 97ms    (New York City)
                - dfw: 146ms   (Dallas)
                - sea: 163ms   (Seattle)
                - sfo: 167ms   (San Francisco)
                - blr: 170ms   (Bangalore)
                - tok: 279.1ms (Tokyo)
                - syd: 294ms   (Sydney)
                - sin: 338.1ms (Singapore)

Interestingly, tailscale ping seems to work fine:

> tailscale ping 100.78.213.17
pong from k8s01 (100.78.213.17) via DERP(lhr) in 59ms
pong from k8s01 (100.78.213.17) via DERP(lhr) in 48ms

(That’s a node that’s on my LAN, so in theory it should be able to connect directly, and it has in the past)

I’m not sure where I’d go looking for logs in Windows, looked in C:\Users\me\AppData\Local\Tailscale and saw a few, but with only 1-2 log entries, looks like that’s not where the main logs are.

Not sure what else to try except uninstalling and reinstalling Tailscale, but I suspect that’d re-issue a new IP address. For this particular machine I don’t really care, so I could try doing that, but figured I’d give figuring out what happened a try first.

Hi. Given your interface does not appear to have an IPv4 address, I think this bug describes the problem you’re seeing: Windows: router configuring interface with no IPv4 address · Issue #1399 · tailscale/tailscale · GitHub. We’re investigating.