To solve the problem of the Signatures button that is not working, it is recommend to uninstall a modern app Microsoft Office Desktop App (Settings -> Apps -> Apps & Features). There is a description of a similar bug in Windows 10 on. However, this fix is inconvenient and not flexible. Specify the full path to the signature file as the values of these parameters. To do it, remove the First-Run parameter in registry key HKCU\Software\Microsoft\Office\\Outlook\Setup and create 2 string (REG_SZ) values: NewSignature and ReplySignature in the reg key HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\MailSettings (for Outlook 2016). You can assign this file as a default Outlook signature through the registry. But it is quite inconvenient since each time you have to press the ‘Signature’ button manually.
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