When sending a message with an attachment in Outlook for Mac 2015, you may see an error message saying "Message could not be saved."
The solution to this issue is to run the Mac Disk Repair utility and fix file permissions:
1. Close Outlook
2. Using the finder, click on "Go" and then "Utilities"
3. Double click on "Disk Utility"
4. Select your hard drive volume, under the hard drive that is installed on your computer (refer to screenshot below), and then click the "Repair Disk Permissions' icon.
Repair Disk Permissions may take a few minutes to run depending on the amount of files you have on your Mac. Once the repair is complete, launch Outlook and you should be able to send attachments.