Synchronizing contacts and calendars in your iPhone with Microsoft Outlook is easy enough if you use one computer, but it gets more tricky if you want to sync with two or more PCs.

Apple’s iTunes software is available for Windows and Mac computers, and will synchronize the iPhone with Microsoft Outlook Contacts, Calendar, Email and Notes. All iTunes needs is a USB cable or Bluetooth link to the iPhone. The only drawbacks are it can only sync your iPhone with one computer, and the phone must be connected to iTunes in order to actually synchronize things. While this might sound reasonable, we’ll see in a moment that there are several options that synchronize data from the iPhone “over the air” without using a cable.

Over the air synchronization constantly keeps things in sync provided the iPhone has a data connection to the Internet – either using the phone’s built in WiFi or its cellular data capabilities. Unfortunately the options for over the air synchronization are a little complicated.

Free Google tools
Google provides a free service to synchronize Contacts and Calendar entries between the iPhone and a free Gmail account. Google also makes a free tool to synchronize Calendar entries between Gmail and Microsoft Outlook, so using this combination you could sync your iPhone calendar over the air to as many copies of Outlook as you want. But this wouldn’t sync your contacts!

Google also makes a tool for people that use a commercial “paid for” Gmail account. This synchronizes Contacts, Calendars and Notes between Outlook and Gmail, but doesn’t sync anything with the iPhone.

Apple MobileMe
Apple’s solution to the problem is MobileMe, which provides over the air syncing of Contacts and Calendar and includes an extra email account and web based storage. But MobileMe costs $99 (£59 in UK) per year, and many people are not willing to spend that much if the only feature they require is iPhone sync.

Other options

There’s a range of other options, all of which synchronize Outlook Contacts and Calendar with Gmail. Once your information is stored in a free Gmail account iPhone users simply need to add their Gmail account to the iPhone to get “over the air” synchronization between their Google account and the iPhone (see our HowTo). However, all the Outlook sync tools we’ve come across either cost money or are beta versions of emerging products.

gSyncit
On sale since March 2007, gSyncit is probably the third-party Outlook sync option with the longest pedigree. gSyncit does an excellent job of synchronizing Outlook Contacts and Calendar with a Google mail account, and it has an impressive list of options to control how items are synchronized and how conflicts are handled.

Each copy costs $14.99, so if you run it on two computers you’d pay almost $30. The product comes with a free evaluation license, which lasts forever but places a severe limit on the number of items you can synchronise.

See our review of gSyncit.

KiGoo
Launched in July 2008, KiGoo is another option for syncing Outlook Calendar and Contacts with a Gmail account. We found installation of KiGoo more awkward than for gSyncit.

In particular, Outlook did not start properly after we installed KiGoo because KiGoo did not automatically install an evaluation license for us. We needed to go to the KiGoo web site and fill in a form to get one. The evaluation license gives full access to all KiGoo’s features for 30 days.

Once it was installed and working, there are almost no configurable options. KiGoo creates its own Outlook folder for Calendars and Contacts, and these contain a copy of your Gmail data. Some people may prefer to have only one set of Contacts and Calendar information, in which case they would be better off with a product that actually synchronizes the existing Outlook data with that in the Gmail account.

KiGoo costs $9.99 per year and each license can be used on multiple computers provided it is for the same Gmail account. Even so, the yearly license means it could still work out more expensive that gSyncit in the long run.

Soocial
Perhaps the most glamorous and certainly the newest option is Soocial, a web based service that syncs information directly between mobile devices and email systems. It supports Microsoft Outlook, Gmail and Yahoo Mail, and connects to any mobile phone that supports SyncML. The list of compatible mobile phones includes Nokia S60, N80, N70, E71, E61, S40 and several others. SyncML is also supported by several Sony Ericsson phones.

Unfortunately it is not supported by the iPhone, although iPhones could be synchronized with Soocial using iTunes.

Summary