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A workaround for Outlook 2013 limitation that does not include the attachment in the reply when replying to a message with an attachment.
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.
Microsoft is reporting an issue with Outlook on the Web that appears to be affecting our Office 365 users.