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Paper clip in MacMail & Outlook for Mac not working

Running Monterey 12.6.3. Suddenly cannot attach anything to Mac Mail or Outlook for Mac with paperclip. Must click & drag file to email I want to send out. What happened & how do I fix? Thanks!

MacBook Pro 16″, macOS 12.6

Posted on Apr 18, 2023 8:08 PM

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Question marked as Top-ranking reply

Posted on Apr 20, 2023 10:07 AM

Hello ChickenMommy,


Usually when clicking on the paperclip, it would open Finder. Are you able to open Finder without issue?


If not, try normal troubleshooting on your Mac that can fix issues with Finder:

  1. Shut down or restart your Mac - Apple Support
  2. Start it safe mode and see if the issue happens there to isolate as much as possible. Make sure to follow the steps fro the type of Mac you have: How to use safe mode on your Mac - Apple Support


Best regards.



3 replies
Question marked as Top-ranking reply

Apr 20, 2023 10:07 AM in response to ChickenMommy

Hello ChickenMommy,


Usually when clicking on the paperclip, it would open Finder. Are you able to open Finder without issue?


If not, try normal troubleshooting on your Mac that can fix issues with Finder:

  1. Shut down or restart your Mac - Apple Support
  2. Start it safe mode and see if the issue happens there to isolate as much as possible. Make sure to follow the steps fro the type of Mac you have: How to use safe mode on your Mac - Apple Support


Best regards.



Apr 20, 2023 6:13 PM in response to Nicholas_B2

Hi Nicholas! Thank you so much for responding to my question. I restarted and the problem resolved. Interestingly, I also was experiencing a problem with Word for Mac at the same time. It wold not let me click & highlight text I wanted to change or delete. I had to hold down the shift key at the same time and sometimes that worked. Sometimes not. However, that also resolved once I restarted my ProBook.

Paper clip in MacMail & Outlook for Mac not working

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