Getting S/Mime Encryption to Work on Internet Explorer with OWA

For some reason, S/Mime encryption is sometimes finnicky. The other day, I was helping my friend try to debug his problem on why his s/mime on internet explorer was not working when he was using the outlook online application. I decided to publish what we found to work for us here so that others may not have to struggle to find the answer.

First, the issue we encountered was on Internet Explorer on Windows 10 when using Outlook WebApp (OWA). After going to settings > mail > s/mime, he had the ability to sign and encrypt…