Using the New Outlook for Mac for personal email and calendar
I can confirm that BC is not the only user experiencing this issue.
I am currently having exactly the same problem with Outlook for Mac, version 16.112.1 (26081720).
When replying to an email, the signature is incorrectly inserted below the original message header (From / Date / To / Subject) instead of directly below the new reply. The same thing happens even when I try to insert the signature manually.
The issue appeared suddenly and, at the same time, Outlook has also become very unstable: it frequently freezes, I sometimes have to force quit and restart the application, and even simple actions such as deleting drafts can fail.
This therefore seems to be an Outlook for Mac client issue rather than an individual signature configuration problem.
It would be helpful if Microsoft could investigate this as a possible regression in the current Outlook version.