Android Deep Inspection problems

[nsumner36]

I decided to finally enable Deep SSL Inspection. I installed a certificate on my Windows devices and my Android phone without a problem. On Windows as a whole things are working as expected and perfectly.

My phone however is a different story. Firstly Android warns me that the network does not have internet connectivity, if I connect anyways things MOSTLY work but there is clearly some check being blocked, or (since I don't see anything blocked) more likely Android doesn't like a MITM attack even if it trusts the certificate.

Duolingo wasn't working until I added to not touch it's SSL certificate on Windows it doesn't care. My email (hosted on Office 365 using the Microsoft Outlook Android app) won't let me open any emails. Again Outlook on my computer is happy. I am guessing that for whatever reason with Android it is more common to staple which certificate to use etc. Has anybody else seen this. Any suggestions or just don't do deep inspection with Android?

[vladv]

I noticed the same behavior here, just now. Did you find a solution to this?