Photo attachments not attached in windows outlook

I am trying to send some photos from my iMac with OS X Lion. I have tried several times both directly from Aperture and inserting them as attachments in Mail. In all cases they end up on Windows Outlook in the message but not as attachments. "Send Windows friendly attachments" is checked. It used to work in Snow Leopard.

Hi,
Please right click on the attachment, then click "Open", does this work?
We can also start Outlook in Safe Mode to troubleshoot if it's caused by some 3rd-party add-ins:
Press Win + R, type "Outlook.exe /safe" in the blank box, press Enter.
Then Outlook will start in Safe Mode, check whether the issue persists. If no, disable the suspicious add-ins to verify which one caused the issue.
Regards,
Melon Chen
TechNet Community Support
It's recommended to download and install
Configuration Analyzer Tool (OffCAT), which is developed by Microsoft Support teams. Once the tool is installed, you can run it at any time to scan for hundreds of known issues in Office
programs. Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact
[email protected]

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