I tried Taildrop between my Macbook Pro and my Windows 10 machine. I also added my Pixel 4 to the network.
All worked fine, but after a few days, the Windows client (I am on 1.10.1, but the problem started with at least 1.10.0) stopped receiving new files. On both the Pixel and the Macbook the sending was successful, but while I used to receive the files on the Windows Desktop, now nothing arrives. Also, and more puzzling, I keep receiving a file I sent once from the Macbook. Always the same file, always on the desktop, but everytime with a progressive number in () at the end of the file name.
Uninstalled, deleted all tailscale-related folders on Windows, to no avail. As soon as I reinstall, re-login and connect the Windows 10 client, I keep receiving the same file, even if I removed it from the Macbook ( ) and without sending anything: the simple fact that I connect the Windows 10 machine makes the same file (a Word document, BTW), appear again and again. As if it were stored somewhere, but definitely no longer in the originating machine. The file has 0 bytes, it looks like it is only a placeholder. The issue does not happen with the Pixel 4 or the Macbook, they work fine.
PS: Edited for typos
PS2: Edited to add the file has 0 bytes