Ever a glutton for punishment, I’m again wading into the calendar/contact synchronisation swamp in an effort to get my address book and calendar details from the Exchange server at work onto the Mac at home. If you’ve followed my previous expeditions into the swamp you’ll remember that the basic problem is that I need to be able to keep track of both a large number of Church appointments, alongside all the work commitments. I’ve been doing that for the past couple of years using a Dell Axim X50v PDA, hooking up with ActiveSync to the Exchange Server.

There are a couple of things that have pre-empted this current attempt to get it all sorted. Firstly, the only thing I now do on the Dell is now my calendar – web browsing, multimedia, everything else is better handled by my iPod Touch which could handle the calendar too if I wanted to reconfigure it to hook up to a PC. Alongside this, the other big driver is that I’m changing jobs, and start at a new company in about a month – as a result I need to get all my contact and calendar details off the corporate Exchange Server.

The tool of choice for the current attempt to scramble my calendar and address book achieve synchronisation nirvana is Plaxo. Now it has to be said that in it’s earlier form, Plaxo achieved a good deal of notoriety by the number of times it spammed people with sign up requests when someone created a profile and added your e-mail address as a contact. However in response to this, they do seem to have one of the most stringent privacy policies I’ve seen – certainly it is an interesting exercise to compare it and the level of control with that offered by Facebook… By way of an example, in both services you’ll quite likely end up with a mix of family, friends and business contacts, with Plaxo you can present a different subset of your profile to each group – key for example if you don’t want your business contacts getting hold of your home phone number. Since Plaxo are also including Facebook like picture and tagging facilities, and FriendFeed like life streaming features, it also allows you to keep business contacts clear of all the embarrassing pictures friends may upload – features sadly lacking from Facebook.

Anyway, my primary interest is in the synchronisation facilities. The list of supported platforms is pretty extensive, in terms of the ones I need it includes support for Outlook, and also an equivalent MacOS X plug-in for the synchronisation on that end. If you’ve currently been using systems such as Hotmail/Windows Live or Google Mail/Google Calendar it can link in to those services too – although at time of writing the Google Mail/Google Calendar connection is not bi-directional. In terms of other devices, Plaxo does have some support for these, but I’m sticking with synchronising those through Outlook and iSync respectively.

I did the basic set up yesterday, and I’m now going through the inevitable process of ironing out the bumps with duplicated data where I had different copies of the same contact in both Outlook and Address Book. The most common problem is having phone numbers in different slots so the synchronisation produces multiple phone number fields all holding the same information – this is usually made worse by there being variations in how a particular phone number is formatted including international formatting, brackets around area codes, and all sorts of stuff like that. Alongside this, there is a bit of time getting used to how e-mail addresses map between platforms. On the Address Book end, addresses are marked as either ‘Work’, ‘Home’ or ‘Other’, and you can have several of these – Plaxo also identifies addresses in a similar way. Outlook on the other hand just has three numbered slots for e-mail addresses. Plaxo has to map these fields to suitable slots in the Address Book structure, and tends to go for ‘Work’ if there is only one. I’m slowly working through getting those sorted using the address book in Plaxo – hopefully once that is all cleared up, the synchronised systems should fall into place.

Calendars I haven’t done that much with so far, which is basically because it is a big job and I wanted to get the contacts sorted first. The fundamental problem is the significant differences between the operational model used by Outlook, and the model used by iCal and Google Calendar amongst others. The intention with Outlook is that the user will operate on a single calendar, and use categories to distinguish different sorts of appointments. iCal on the other hand positively encourages you to work with multiple calendars, so for example I have a work calendar, a home calendar, a Church service calendar, a choir calendar and so on. What this does is allow people to share calendars, so for example the choir schedule could be kept on a single shared calendar and distributed to all members. The different calendars roughly correspond with my Outlook categories, and this is what most synchronisation solutions tend to map. However, it is incorrect to say that Outlook doesn’t support multiple calendars – it does, however the support has always been obstructive. For example until the 2007 release you couldn’t overlay the different calendars – only side by side views were available. When it comes to synchronisation with a PDA, only a single calendar is synchronised, so effectively you can’t operate with multiple calendars using Outlook if you’re synchronising on from there. The idea of multiple calendar support seems to very much be to allow you to look at other peoples calendars, but then the implication is that you’re going to put relevant events into your own calendar.

The issue is that Plaxo doesn’t synchronise categories with calendars. The Plaxo model supports multiple calendars, so your multiple iCal calendars map to multiple Plaxo calendars, and thereby onto multiple Outlook calendars. Whilst this works fine if you’re synchronising something like an iPod Touch or an iPhone using iSync as they all understand and can deal with multiple calendars – even if the devices appear to work on a single calendar model. Doing the same from Outlook, and especially with a Windows Mobile device, you’re back into single calendar world, and you’ll have chunks of your schedule missing. Since Outlook can cope with multiple calendars, albeit badly, I could probably move to syncing the mobile devices with iSync and use Outlook 2007 at the PC end – but I’ll have to stop trying to keep the Dell Axim in sync. I’ll also have to go through a process of splitting my calendar out, as it’s currently all rolled up into a single categorised calendar, rather than the multiple calendars that iCal would support.

So, it’s so far, so good – Plaxo seems to be working okay, and I haven’t come across any of the annoying time and date shifting problems that beset any attempt to use Entourage hooked up to an Exchange Server. The real challenge though is still to come – when I try to pick apart my calendars…