HTTP 500 Error using Exchange ActiveSync on Exchange 2003

Just a quick one so I remember this next time!

One of our clients hooked up their first mobile device last week (it was an iPhone!)

They called us to ask for the details but they were constantly prompted for the password. I was visiting site the same day so had a look myself. The settings had been entered correctly so i logged onto the server and checked the IIS logs

I could see entries for the iPhone connecting but nothing in the security log that indicated a problem with the user name and password

The next step was to use the excellent website to see if it could connect. It couldn’t and i got a HTTP 500 error with a link to click on which eventually led me to:

Basically when using a single Exchange server there are some steps you need to take as the virtual directory ActiveSync uses needs HTTPS disabled whereas i need it enabled for OWA (the full technical details are in the KB article – your device is still connected to the server over HTTPS)

The problem doesn’t occur if you have a front-end/back-end Exchange setup or if you are running SBS 2003 as the connect to the Internet Wizard takes care of that for you (check the steps in the KB article and compare it to your SBS…they will be the same)

I also came across a great blog post by Corey Gilmore, with the full set of steps needed to configure a single Exchange 2003 server for ActiveSync (including ISA configuration) with screenshots so there is no need for me to reproduce that here 🙂

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Andy Parkes is Technical Director at Coventry based IT support company IBIT Solutions. Formerly, coordinator of AMITPRO and Microsoft Partner Area Lead for 2012-2013. He also isn't a fan of describing himself in the third person.

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