Short answer:
The error “Not authorized to send Apple events to Microsoft Outlook” means macOS is blocking Xink from communicating with Outlook. Allow access under Privacy & Security → Automation.
Summary: This error occurs when macOS privacy settings prevent Xink from controlling Outlook. Granting the correct Automation permissions resolves the issue.
Allow Xink to control Outlook
Go to System Settings (or System Preferences) > Privacy & Security > Automation, and enable access for Xink to control Microsoft Outlook as shown below:
If Xink is not listed under Automation
If the option does not appear, reset macOS permissions and trigger the prompt again:
- Quit Xink.app.
- Open Terminal and run:
tccutil reset AppleEvents
- Open Xink.app from the Applications folder.
- Click the Xink menu and select Preferences, ensure Outlook is selected, then close the dialog.
- Click Update signatures.
Allow the permission prompt
macOS should now display a permission dialog. Click OK to allow access:
Troubleshooting
- No prompt appears? Restart your Mac and repeat the steps.
- Still blocked? Ensure Outlook is installed and opened at least once.
Next steps
After granting permission, run Update signatures again and verify that Outlook updates successfully.
