If like me you have encountered problems setting your iPhone 3G up to sync with Microsoft Exchange on SBS 2003, read on.

Judging by the posts in forums all over the Internet, many people are having problems connecting their iPhone to SBS 2003 Exchange. You may be getting a certificate error come up (due to having a self-signed certificate on your SBS 2003 server), but you accept this and the account appears to verify. However, your calendar and inbox remain defiantly empty. I managed to solve this, so check out the following steps and see if it can fix it for you.It’s important to bear in mind that Exchange is something of a behemoth, and different configurations abound. Our server is running Small Business Server 2003 with a single network card and is standard configuration from the SBS setup wizards. If you have a similar environment, your chances of success are high.

Caveat: whilst this all worked smoothly for me, I cannot guarantee this will be the case for everyone – Microsoft products can be tempremental at the best of times! So, if anything goes drastically wrong, it’s not my fault – you use these notes at your own risk.

I don’t know for sure whether the iPhone will work smoothly with the SBS 2003 self-signed SSL certificate. It may work with it, and it will probably work if you switch SSL off, but I took the decision to buy an authenticated certificate as they’re not much money. I can arrange an Equifax certificate for anyone for £50 – get in touch if you want me to do this. Or you can do it yourself. Just avoid intermediate certificate providers like GoDaddy, as these require extra configuration on the iPhone. If you are going to buy a certificate, here’s the process:

• On your SBS box, go to Start > Administrative Tools > Internet Information Services (IIS) Manager
• Expand the server tree on the left, and then the Web Sites tree
• Right click on Default Web Site and click Properties
• Click on the Directory Security tab and then click Server Certificate to start the wizard
• If you don’t have a certificate you can create one (unlikely) – if you do have one, you will have to remove it. This will kill secure connections until you replace it.
• After removing the self-signed cert, run the wizard again and create a new request – don’t choose the option to send it directly to a certificate authority.
• The wizard will create a CSR and save it in a text file. Open this text file and copy the certificate then paste it onto your chosen certificate provider’s order form. Copy the whole certificate request, but only the certificate request (extra spaces will kill it) – it should start and finish with five hyphens —–
• Order your certificate and use the same wizard to paste in the certificate sent to you by the provider – job done

The certificate alone is not enough to fix the problem. The real problem is that SBS 2003 ships with Exchange 2003 SP1, whereas iPhone requires at least Exchange 2003 SP2. So, we need to install Service Pack 2 for Exchange, but before we do this, we need to backup our information store – just to be on the safe side. Choose Start > Run and type ‘ntbackup’ (without the apostophes) then press enter. Follow the wizard.

When you are done with your backup, we need to patch Exchange. You cannot do this with Windows Update as Microsoft have not released an official Exchange 2003 SP2 for SBS 2003. However, you can download the service pack separately and apply it – it works with no problems.

Download SP2 here: http://www.microsoft.com/downloads/details.aspx?familyid=535BEF85-3096-45F8-AA43-60F1F58B3C40&displaylang=en (link opens in a new window)

Extract the service pack to the desktop or wherever suits, and find the upgrade.exe – double click it. When the upgrade finishes, reboot the server just to be on the safe side.

Now you should be able to add the Exchange account to your iPhone. Give it a few seconds and your inbox will start filling up.

If it doesn’t, and you’re connected with WiFi to the same LAN that the server is on, it could be that your router doesn’t support loopback. Remember that you put in an external DNS name for your server address, and some routers can handle external DNS names that loop back to the same IP address. If this is the case, switch off WiFi on your iPhone (it’s in the settings) and it will connect via EDGE or 3G instead.

This might seem like a lengthy solution, but the key is really the SP2 thing. The vast majority of SBS 2003 servers out there will be Exchange 2003 SP1, which just won’t work.

Much thanks and kudos must go out to my lifelong chum and Microsoft guru Mike Southby, as he gave freely of his time to help me sort this out.

Let me know if this helps anybody else.