Anytime I've done something like this before I've made use of the Mac address book application and iSync. iSync has a habit of being rather 'out' of sync with the latest phones and in the case of the Blackberry Pearl my usual fears were realized. No support at this time - either USB or Bluetooth.

Thanks to this post however I discovered that a 3rd party application called PocketMac SyncManager, now officially licensed by Blackberry makers Research in Motion, and available to end users for free, does just what I need it to do only with some significant caveats. The problems are not insurmountable however, and if you take things slowly and carefully, things will work out fine.

Firstly you must approach your 1st Blackberry sync in the following order...

• Open up PocketMac Sync Manager by itself, with no other applications open (Dashboard is ok)
• Make sure the Blackberry is turned off and connect it via the supplied USB cable
• Turn on the Blackberry (I chose not to enable the USB disk mode and this worked)
• Click the Blackberry icon in the Sync Manager application, confirm all the various options, and then click Sync

Doing anything else it seems throws an error and by the looks of it many people have experienced this problem.

My needs were pretty simple - I wanted to transfer over my Address Book contacts and nothing else. I don't use iCal, nor Entourage, nor any of the other supported apps (Lotus Notes ???). This is a shame because I do sometimes use Palm Desktop as a calendar (it's way better than iCal) but this is not supported.

Back to Address Book...

There are a few quirks that you should be aware of before proceeding...

• There is no way to DELETE ALL contacts on the Blackberry Pearl. At least not that I've found. For this reason, it's an extremely good idea to clean up your address book first and in full before doing your first sync. You can backup your Mac address book very easily, so I suggest doing this at the very beginning. This way you can do a proper spring cleaning, getting rid of anyone you don't speak to anymore safe in the knowledge that you can retrieve their details in future if needed!
• Field matching between the Mac Address Book and the Blackberry Address Book is VERY sketchy and uses a basic field mapping system. Some fields simply aren't transferred at all. I've researched the mappings below but be aware that you will need to reassign your field designations in Address Book BEFORE syncing or you will be without those fields on the Pearl. This is no insignificant issue, I had many cases where the fields did not transfer.
• Once you have done your first sync and are looking to make tweaks and changes, it is okay to have Address Book open on the Mac alongside SyncManager (but you should not be in Address Book edit mode), and it is okay to have the address book application open on the Blackberry, although not open on an individual entry. Hopefully this will speed up your tweaking process.
• Making changes to a field name or contents in Mac Address Book does successfully get recognized by the application and is updated the next time you sync.

As mentioned above, field names in the Mac Address Book are mapped to fields within the Blackberry Address Book. Custom field names (set in Mac Address Book) do not transfer over despite there being the presence of 'User' fields on the Blackberry, and some standard fields do not transfer over either. Some field names are changed! The full details are below...

One little gotcha to be aware of is that within the Mac Address Book it is perfectly okay to have different fields with the same field name, but SyncManager can't handle this.

For example I had several cases where I had multiple 'mobile' entries for people - only the first one was transferred. This was a major issue for me and very annoying.

The solution was to go through these entries and change them to different field names. I relabelled a lot of fields as 'main' for example to get them over to the Blackberry as 'Work 2'. For some friends of mine for instance I had custom fields for 'mum' or 'usa home' or whatever. I made use of the Notes feature to remind myself in future what certain numbers represented. Being relabelled as 'Work 2' I would have no idea what these numbers were if I hadn't done this.

Hopefully the situation will change in future with an update to the software and if it does (and you become aware of it) I would kindly ask that you help other readers by using the comments section below. With RIMM now officially recognizing SyncManager, hopefully the boys in Windsor will ensure these quirks are worked out of an otherwise very useful bit of software.

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