I’ll keep this post short.. I swear this time haha

The Story

I recently blogged about using OPNsense as a reverse proxy for Exchange. This was really nice, and I was able to access Outlook Anywhere, literally from anywhere with owa. However…

The Problem

For some reason I could not connect with Active Sync… Even when I had my phone in the same network pretty much. I thought it might had to do with the self signed certificate (I should have known it was not when selecting “Accept all certificates” under the connections options still didn’t work), so I wastefully exported the certificate and key from my OPNsense server and imported it into the Exchange ECP, and assigned it to the IIS and SMTP services. (I’m probably going to change these back to the self signed as I don’t really have intentions on completing these steps every 60 days.

Since I didn’t want to use my account to test on Microsoft test site (this is a life saver), I used a account and email I was setting up for my colleague… and it passed… I was shocked. (At first I thought it was cause of the certificate changes… I soon found out.. it was not).

So I tested the same connection settings on my phone and it worked!

Woo Hoo!

The Real Problem and Solution

My happiness was sort lived once I attempted to add my account…. which still failed…. what the heck? I had all the settings the same exc…ep…t… my account…. wait a minute…. Google… WTF! Admins can’t use active Sync?!?!? Why isn’t that more specified in the documentation! I was aggravated about this for days… cause of something that was sooo simple!

I’ll cover exporting and importing certificates for other uses in a nother blog post. I just wanted to get this one out cause even though I had configured everything in my previous blog post about using OPNsense as a reverse proxy correctly, I wanted to follow up on why Active Sync was working for me, cause everything else on online guides made it sound so simple, and it rather is… until you find out a little secret GEM MS didn’t tell you about…