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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.
What is the maximum size for an e-mail message with attachments?
The maximum size of an e-mail message on all University e-mail systems is 35 MB. Alternatives for sharing large files are OneDrive and Big File Drop Box.