MAC Error: Not authorized to send apple events to Microsoft Outlook

Please go to your MAC System Preferences -> Security & Privacy -> Privacy -> Automation and set the checkmarks for Xink as shown in the image example below.

If the above options do not show, please perform the following steps below. 

  1. Quit if it is running.
  2. Run the following command from a Terminal: tccutil reset AppleEvents
  3. Start from the Applications folder.
  4. Click the Xink menu and choose "Preferences".  Make sure that Outlook is chosen.  Close the dialog.
  5. Click "Update signatures".

Hopefully, macOS will now show you this prompt where you must click "Ok":

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