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For about 10 years my colleagues and I have used iChat, then Messages to exchange images for work (we use AIM). A year or so (maybe longer) we could no longer transfer images back and forth. The recipient never got an alert that a file is trying to be sent to them, but on my end Messages claims it has been sent.

However, looking in Console I see errors when trying to send the image:

2/4/16 3:46:05.000 PM kernel[0]: Sandbox: com.apple.messag(95477) deny(1) file-read-data /Users/nnhubbard/Library/Messages/Attachments/54/04/784F9421-C5B4-4CB8-B3F8-2426F4D783AB/longo.jpg
2/4/16 3:46:05.622 PM com.apple.messages.TranscriptRenderingService[95477]: [Warning] Transfer: unable to create image for longo.jpg

This is a very frustrating problem that a number of us have, and we have all done research to try to fix the issue.

** Strangely we CAN transfer .zip files. **

Does anyone have any idea what could be causing this and what these error might mean?

OS X 10.11.1, Messages 9.0

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