Synchronising Calendar and Contacts with Outlook

by Maskil on 8 Jun 2010

Microsoft Office Outlook Icon

Image via Wikipedia

The requirement sounds like a simple one: synchronise my Outlook (2003) Calendar and Contacts (especially) with Gmail, Hotmail, or another secure, reliable Webmail or other service. As a lifelong corporate IT person, I still like using Outlook as my e-mail and PIM client (although I’m now 2 versions behind). I would, however, like to have my Contacts and other Outlook PIM stuff backed up and synchronised with a cloud service.

Surely it can’t be that difficult? Apparently it is, even if you’re prepared to pay for it. Here’s my experience testing out a number of options over the past couple of days. Let’s go through them, starting with the big guys.

Google Apps Sync for Microsoft Outlook

My main e-mail account is a Gmail account, so synching with Gmail on the Web would have been first prize. Not only that, but Google already has a tool to do exactly that, Google Apps Sync for Microsoft Outlook. You can download and install it freely, but it won’t work with a e-mail address, nor with Google Apps Standard Edition. It only works with the premium editions of G/A.

Here’s my request to Google to open up this app to the peasants as well:

Make Google Apps Sync for Microsoft Outlook available for Google Apps Standard Edition AND native Gmail. This would be a “killer app” for Google Apps/Gmail, and cement Google’s role as IT infrastructure provider to the world!

I’ve posted it on the relevant Google site. Please sign in and vote for it here:

Product Ideas for Google Apps (administrators) – Google Product Ideas

Microsoft Office Outlook Hotmail Connector

Microsoft also has a product that should be capable of doing the job, the Microsoft Office Outlook Hotmail Connector. The problem? It does what it’s supposed to do, but not what we wanted it to do. What do I mean by that? If asked in that much detail, we (the users) would have said we wanted to synch our Windows Live/Hotmail account with our default Personal Folders (.pst) file in Outlook. Instead, the Connector creates a whole new Hotmail hierarchy of folders inside an .ost file and syncs these folders with Hotmail on the Web.

Rather than a mechanism to sync Outlook with the Web, we end up with a way to read and write to our Hotmail Web stuff from within Outlook. Not quite the same thing.

From the (quite extensive) testing that I did, it appears to make no difference whether the Hotmail account is set as the Default e-mail account or not; your existing folder structure is ignored (effectively orphaned) in favour of the new folders.

I would have been happy to do a once-off migration and use the new folder hierarchy the Connector creates, but applications such as my Nokia software assume it will find my stuff where God (OK, Microsoft) originally ordained it should be. It quite rightly wants none of that stinkin’ .ost stuff. I’m guessing that most other 3rd-party apps will have the same limitations.

I even thought of syncing within the same Outlook install i.e. keeping the two Contacts folders, etc., in sync, but I haven’t found a utility than can do that.

I’m guessing that there’s not much hope of persuading Microsoft to write a new version of the Connector that does what we want it to (based on the feedback I’ve seen out there, I’m far from being the only one). As far as they’re concerned, they’ve addressed the need.

Microsoft Office Outlook Hotmail Connector overview – Outlook – Microsoft Office Online


This was the product I’d bookmarked to use after I got rid of Plaxo. There is still a free version, but it’s limited to 250 entries and 3 connectors. The unrestricted version is $30 (R225 per annum in my money). I registered for the free version, but the first 2 connectors I tried to set up (Outlook and Gmail) were filled with dire warnings about known bugs and Beta software. Let’s get this straight. You (Soocial) want me to pay you $30 per annum for the privilege of debugging your crappy beta software? I don’t think so. I guess they’ve based their business model on Plaxo’s, but Plaxo at least pretends to do more than just sync your address book for their ask of $60 per annum.

(Perhaps I’m being unrealistic, but I can register a Domain and get DNS, some Web hosting and a whole bunch of other free stuff thrown in for $10 per annum, so $30 seems a little excessive to me.)

Soocial Hassle-free contacts


I didn’t get too deep into this one, although it appears to work for some. It didn’t inspire confidence in me, however, sending my password to me in clear text in an e-mail message. When importing and merging contacts, it seems as if one is always a single wrong mouse-click away from spamming family, friends and contacts in perpetuity. I tired of walking this tightrope very quickly and deleted my account (hopefully permanently).

UNYK Address book

For now, it looks as if I’ll still be backing up my contacts using good old-fashioned exporting to .csv and .pst files, and importing them to strategic locations around the Web.

And if anyone finds anything that really, really works to do this simple job, please let me know!

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