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Why do I receive the error "Message could not be saved" when sending a message with an attachment in Outlook for Mac?
You must run Repair Disk Permissions utility that may take a few minutes 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.
How do I reply to a message with an attachment and include the attachment in my reply in Outlook
A workaround for Outlook 2013 limitation that does not include the attachment in the reply when replying to a message with an attachment.
Error message when attaching files in Outlook on the Web: "Something went wrong while connecting to OneDrive for Business"
Microsoft is reporting an issue with Outlook on the Web that appears to be affecting our Office 365 users.