I have a script that creates a .htm and .txt file in the %appdata%\Microsoft\Signatures folder.
I set the signature via registry using:
NEW-ITEMPROPERTY HKCU:'\Software\Microsoft\Office\15.0\Common\MailSettings' -Name 'NewSignature' -Value $SignatureName -PropertyType 'String' -Force
NEW-ITEMPROPERTY HKCU:'\Software\Microsoft\Office\15.0\Common\MailSettings' -Name 'ReplySignature' -Value $SignatureName -PropertyType 'String' -Force
Everything appears to work except the signature does not show in the compose window by default. It will let me add it manually.
If I open up the signature settings area within Outlook, make zero changes (I couldn't if I wanted as it is greyed out) and then close it, the signature starts showing automatically in emails again.
What am I missing? What does opening then closing the signature window do?
Should anyone else come into this issue it was solved by deleting a registry entry.
REMOVE-ITEMPROPERTY -path "HKCU:\Software\Microsoft\Office\15.0\Outlook\Setup\" -name "First-Run"
Adding this in and having it run while Outlook is closed fixed the issue