Hi Jason,
Are you trying to sending the same attachment in Windows Outlook and Outlook for Mac? Based on my experience, an email or attachment file consumes different storage space in different Outlook clients.
According to the official article, the limitation of an email including attachment is 25MB.
https://technet.microsoft.com/en-us/library/exchange-online-limits.aspx
Currently, there is official solution to raise it. I understand it is a practical requirement for our customers to send attachment that is large attachment. Therefore, to improve our services and better meet your needs, I would invite you to submit feedback to our relevant team. Many features have been designed based on our customers’ valuable comments. You time and understanding are highly appreciated.
Thanks,
Alex