The question I have is about workflow for updating or creating new entries. Strongbox doesn’t recognize when I’m creating a new login, or offer to enter a strong password and save. I had to manually create a new entry, manually cut and paste the pw to the web form, then go back and manually type the URL.

Clicking the key icon in the field was not triggering any response, when it should've been showing options.Then clicking "strongbox" pop up a dialog where I select "Create New Entry" and everything works from there.

Edit: The issue turned out to be that my database was in the root of my icloud storage, as opposed to being inside the Strongbox folder. After correcting that everything worked as it should. So do not simply drag a database from the Mac to iCloud Drive — create a new database in iCloud which will also create the folder "Strongbox" it needs to reside in. I am not sure if this is simply a path issue or if there is something special about the folder that enables the functionality that wasn't working properly.