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Can't get iPhone to sync with SBS 2003 server

One of our clients just replaced her BlackBerry phone with an iPhone. She is having an issue where she can't sync the iPhone with the company’s SBS 2003 server. I contacted Apple and they stated that an encryption on the SBS 2003 server might be the issue. I think that the issue might be the BlackBerry Server (Enterprise) on the SBS.  Any ideas?  Thanks.
Watch Question

Do you hace RPC over HTTP active on the SBS Server or are you planning on using a different protocol to connect the phone to the server?

BES should not affect the iPhone as it does not directly communicate with the devices, but rather talks to RIM.


Yes BAYCCS. I do have RPC over HTTP active on the SBS Server.
Top Expert 2011
Please have a read through my article, check your iis settings, run the tests, fix any erors and if you get stuck anywhere, let me know for more guidance:


RPC over HTTPS has nothing to do with the iPhone or mobile phone connectivity, it is used to connect Outlook to the server remotely.

Blackberries can use POP3 or OWA to connect to your server.  The iPhone will use Activesync for push mail or POP3, although Activesync is what you will want to use as it syncs the calendar, contacts and mail.
In order for ActiveSync to work, RPC over HTTP needs to be setup and working properly. I have an iPhone and use ActiveSync to connect to my Exchange with no problem.

Have you tried setting up a profile in Outlook to connect to the server from outside the network using RPC over HTTP? Please verify if that is working correctly. If you can't connect, her phone will most likely not connect either and most likely the issue is server related. RPC over HTTP is a pain in Exchange 2003 and got much better in 2007.

Just b/c his client used Blackberry doesn’t mean that she is using BES server, I am not sure where this assumption came from?
Alan HardistyCo-Owner
Top Expert 2011

@bayccs - RPC over HTTPS has NOTHING to do with Activesync.  Please check your facts before posting incorrect information as a fact.

If RPC over HTTPS is working, then Activesync stands a fair chance of working but the IIS virtual directories used for each feature are different and although they both use the Exchange virtual directory, RPC uses the RPC virtual directory and Activesync uses the microsoft-server-activesync virtual directory, so if RPC works, Activesync can still not work if the IIS settings on the microsoft-server-activesync virtual directory are incorrect.

@relentlessmsp - My article will walk you through the pre-requisites, IIS settings, the test site (https://testexchangeconnectivity.com) and offers solutions to the errors that you might face after running the test.

Please pay no attention to any suggestion about RPC over HTTP - that will not help you here.
HiI have just come through the iPhone connectivity issues some days ago.  The RPC over Http will definitely not help you.  alanhardisty's article resolved my problem but you MUST follow it to the letter!  I printed the article and created an Action sheet to ensure that I had carried out each task described in the article.  Once all the boxes had been ticked on my Action sheet, I was then able to focus on the iphone settings.  Trust me! It will save you a lot of time! and it works!!  Hope this helps