Using older versions of Outlook for Mac for personal email and calendar
Same issue here.
Did some digging since I thought my IT department made a change to the configuration again. There is a default setting named DisableSignatures which should be false (0) by default. However, when I read the setting, the command indicated it wasn't set. I set the value to 0 (false) and restart outlook. The signatures feature started working again. You'll need to use the mac terminal to run the two defaults commands (no root access). Since the command runs under the current login, you'll need to run it for each login if you have a shared login system. Appears to be broken in this version 16.63 which I upgraded to on Friday.
Interesting side effect, I pushed the add button a number of times in the dialog. Once I enable signatures again, it appears it was tracking me all along so now I have a ton of the Untitled Signatures setup.
Commands and output. Note there is no output for the write version.
// Reading the value
defaults read com.microsoft.Outlook DisableSignatures
2022-07-18 09:42:48.322 defaults[20309:460217]
The domain/default pair of (/Users/[username]/Library/Containers/com.microsoft.Outlook/Data/Library/Preferences/com.microsoft.Outlook, DisableSignatures) does not exist
// Change the value to false
defaults write com.microsoft.Outlook DisableSignatures 0