I’ve been having far too much fun with contact sync in the last week or so. My mum has been very happy with her Plaxo account to sync contacts between Hotmail and her mac, so I decided to give that a go. I think it was mid 2007 when Microsoft released the upgrade from Vista’s mail client to Windows Live Mail – it didn’t tell me it was uploading my entire contact book to Windows Live but I finally had my addresses synced between home and work so I didn’t mind too much.

I’m not sure if that turned out for the best or not, because Plaxo’s contact slurp from Windows Live has a rather critical flaw. It totally ignores the messenger account address (despite having a field for IM accounts). This means that for my MSN-only contacts who had no name and no email address other than their messenger contact, Plaxo imported a blank field. I’d deleted about 10 people before I happened to reload MSN and it warned me that it was about to delete them from my contact list – luckily I was able to write them all down and re-add them.

I had to spend a couple of hours filling in names for my MSN contacts, re-importing them into Plaxo and having to manually copy over the IM address, but it all synced down to the Mac nicely. When it works, Plaxo is cool.


It was tonight that things got really trippy. About 6 or 8 months ago, I borrowed a USB bluetooth adapter from a mate to try syncing my Vista contacts to my phone. That crashed and burned horribly with no Vista driver for it and a discovery that I couldn’t use it anyway – Vista will only sync contacts with Windows Mobile. The phone’s PC software does support the old PIM standard transfer but the only worthwhile windows software that supports such a thing is Outlook.

Anyway, on a whim I decided to plug it into the mac (no BT on an iBook this old). 5 seconds later the BT icon had appeared in the menu bar, my phone connected without any issues and it was even recognised by iSync. That was when I realised I hadn’t finished fixing my phone’s contact book – I didn’t have any data cable for the previous phone so I’d used the SIM card to transfer all my contacts. People with multiple numbers had been expanded (SIM entries only support one number) and quite a few people were listed under nicknames so it wouldnt’ sync properly.

So yet more hours later I had used the PC software to move everyone to the Phone memory and update their info, and I was finally ready to sync. Even though iSync gave me a heart attack saying it had deleted the address data for about 20 people – I just turned off the Plaxo sync so I could check them against the Plaxo copy – it must’ve changed it’s mind because they’re all intact.


After all that effort, it was really trippy to see the phone numbers I’d collected automatically inserted into the address book entry next to the email addresses, and all of that data uploaded to my phone. It even managed to put my calendar data in the phone along with alarms – thanks to the odd combination of OSX, Plaxo and Microsoft I finally have my contacts synced to three places (home, work, mobile) which I’ve been dreaming about for years.

I don’t regret my decision to stick with Windows for the 10+ years I’ve been using it. But I am glad I’ve finally made the move to OSX and when I get sick of shoehorning myself into a dead laptop I’ll be buying a mac mini.

Not that this means I’ll never go back – one of the advantages of running everything off either a fileserver or offsite is that my contacts, mail and even documents folder are synced to both Windows and OSX 😉