You can put me in the long time Mac/iPhone user group. Not only do they make excellent hardware – Apple really goes to extraordinary lengths to integrate the software and user experience.  A Macbook Pro has been my daily driver for work for nearly 3 years. Using a Mac all day every day is very enjoyable; but one little irritation has nagged at me.  Images in the Messages MacOS app are broken!  The image would never appear.  An icon with a filename would appear but that was it.

At first I thought it was probably the corporate VPN connection that might be blocking them. Work had me so busy, I just ignored it and opened my phone each time a message with a picture came in.

Today there is more work than ever to do; but for whatever reason – I really had to scratch that itch this time!   After some experimentation the solution presented itself!

The Messages app stores incoming images  in a folder (Library/Messages/Attachments).  Upon examining my system, I found a zero byte file (/Users/your-user-name/Library/Messages/Attachments).  That seemed pretty odd.   A bit of searching and I found an article on the Apple Communities site.

Remove that file and create a directory with the same name.

When you restart Messages any new messages with pictures should work just fine!

A few thoughts:

• It is unclear how this got “broken”.  Maybe something happened when my computer was initially setup
• There is no obvious way for Messages to clean up the Attachments folder.  It might be a good idea to clear that out once in a while – particularly if you use your computer for work <privacy> or have images you don’t wish anyone to see </privacy>.
• When you restart Messages any images already in your text streams will remain broken.  Since the folder didn’t exist when they were recieved there was no way to cache them.