Thank you for that information. Since you had not included any of this at the beginning, people have to start at the beginning for troubleshooting. Given that all is hosted inside and others are not experiencing the issue, I suggest you check your Outlook settings to see if you have something different than others in the office. If you are unable to locate something there, you may wish to head over to Microsoft and their Office for Mac forums for assistance, unless your IT department is aware of all the settings you should have on the computer and Outlook to handle your mail. Here is the proper answer to this problem. My Macbook Pro had Office 2016 for MAC version 15.25 installed and i set my updates to manual and was able to send 27MB attachment.

Jan 21, 2015  outlook 2011 maximum Database size I have a mailbox with 65 GB in size, there is from time to time a syncing issue. Is there any limitation for the number of items that can be stored in Outlook 2011 (For mac)?

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The other Macbook Pro had Office 2016 for MAC version 15.33 updates set to auto. I updated both to Office 2016 for MAC to 15.36 the latest neither could send attachments larger than 25MB. I uninstalled my Office and reinstalled to version 15.25 and can once again send attachments larger than 25MB. This had nothing to do with my mail server or the ISP since the the email wasn't even released from Outlook. Thanks for everyone's time. That is why I referred you to Microsoft to see if it was a setting in Outlook. It may also be something that you can adjust if you check with them, since all it seems is that you removed an update to Office that made the change.

I suspect that Microsoft should be able to answer that question, unless you can see information about what the incremental updates to your Office 2016 would have done to adjust Outlook. I was able to check my Outlook 2016 on my Windows laptop, and got this from Help. Does not seem there is a workaround other than that mentioned, and what you did with installing different versions, but it seems there is a 20MB limit at this point. Send large files with Outlook You’ll receive an error message if you attempt to attach files larger than the maximum size limit.

There are a few ways to work around this size limit, including using a file sharing service or compressing the file. Outlook limits the size of files you can send. This limit prevents your computer from continually trying to upload very large attachments that exceed the limits of most Internet service providers. For Internet email account. Such as Outlook.com or Gmail, the combined file size limit is 20 megabytes (MB) and for Exchange accounts (business email), the default combined file size limit is 10 MB.