Why can I not upload an attachment in exchange?

[Windows Central Question]

I have recently upgraded to windows 10 which has worked fine. However, I am no longer able to upload an attachment to emails through my exchange account. I am a professor and need to be able to do this through my exchange account. When I try to do this it shows that it is attached; however, once the email goes through it is not there and the students are not receiving it.

 

[stevesu]

Hello Professor,
Can we get a bit more information so we can better assist you?
What kind of file is it?
Have you been able to upload this kind of file in the past?
What program are you using? outlook; outlook.com; mail; other
Have you tried using one of the other programs to perform the same task?

I recently had a couple issues of my own - I was having problems with the Mail app. It's new and buggy (for lack of a better term), so I launched Outlook.com and performed my task. This happened to me twice and twice to my wife as well.

EDIT - To clarify - An OS (operating system) does not care about the file you upload and would never care to "block" you uploading said file. However the other questions I asked will help troubleshoot and determine the culprit, which could be, for example: IT, firewall, program/application.