Encrypting the database

What information do you need?

Yes, that is quite annoying. I think we can still improve the message here, so the user knows that they should open from the TrayIcon. Another solution is to make a small window with an embedded browser tab, so the user’s regular browser is not used.

This would allow us to log in automatically without compromising security.

Yes, if the secrets are not migrated as well, then it does not really work.

That depends on the restore I think.
If you re-install the system image, it is (in most cases) the same as migrating to a new system.
You cannot generally just copy in everything in AppData and assume it works on the new system?

Yes, that is what we need to mitigate as well as possible.
However, I don’t consider the server database a thing that should be the primary backup of settings. It is a working copy of settings and can be kept for convenience, but it should not be the primary source. Encryption passphrases should be stored elsewhere in case the system is lost, and if they are, the database is not critical IMO.

Happy to hear other arguments.