Taildrop not working from iOS to Fedora 36

Hey everyone,
Started playing with Taildrop today and ran into an issue sending from my iPhone to my Fedora laptop. I get an error notification: “Failed to share file with ray-t480s. Reconnect ray-t480s to Tailscale and try again.” See attached screenshot.

  • Sending from Fedora to the iPhone works without issue
  • Both devices are owned by my user
  • Running sudo tailscale file get -wait -verbose showed no output at any point

Any ideas what could be happening here?

Thank you!

Hey @skoobasteeve! I’m spinning up a Fedora 36 VM to test this out and see if I can reproduce it. I’ll report back here with my findings. Appreciate your patience in the meantime!

Hey again @skoobasteeve ! I tried this out a few different ways and was only able to reproduce the error message when my destination device actively required re-authentication. That’s expected, though—my device was no longer authenticated with Tailscale so it couldn’t receive the taildropped file.

To make sure we’re covering all our bases, on your Fedora machine, can you run sudo tailscale up --force-reauth, go through the authentication process, then try dropping your image one more time?

If that doesn’t fix up the issue, reach out to us directly at Contact our support team · Tailscale and mention this forum thread so we can take a closer look at your account and look at our logs.

Hi @keli , really appreciate you jumping on on this. As you suggested, after a few runs of sudo tailscale up --force-reauth and re-authing the iOS device, Taildrop is working smoothly both ways.

Thank you for your assistance!

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