Hi @kwaegel , thanks for raising this issue! 🙏
I've taken some time to reproduce the tasks you've mentioned here and found that I did see some unexpected weirdness with Watchtower's results (particularly around re-used passwords). This seemed to be independent of the app's sync, so unfortunately I don't have much in the way of advice on that right now.
However, I have reported the issue to our developers, with links to both this conversation and my own testing, and we'll be sure to look into this further. 👍
I should note quickly that Watchtower will sometimes display different strength ratings for the same password depending on whether that password was created by the app's password generator or entered manually. This is because we have the ability to reliably rate the strength of passwords generated by the app, whereas it is much more difficult to do so for human-created passwords entered by the user.
Thank you again for letting us know, and we'll make sure to dig into this one!
ref: dev/core/core#11538