BOINK

Do you remember PIM?  The acronym first became popular when PDA’s like the Apple Newton and Palm Pilot first appeared.  The concept still exists today, though most have stopped calling it “PIM”.  The concept is simple…

We communicate over email, so email functionality is part of it.  To communicate, you need a contact list, so an address book of some sort is part of it.  And you typically arrange meetings with people so you need a calandar as part of it.  But the calendar needs to be capable of sending invitations over email (and of course accepting them), so it needs to also tie in with your address book and email program.

Bored yet?  You should be.  The concept has been around for almost 20 years.  To date, only two companies have got it right: Microsoft and RIM.  And Google will be next.

Technically, only email really knows how to work over the Internet.  Calendars and Address books don’t, although CalDAV is beginning to change that for calendars only.  Why is working over the Internet important?  Simple: syncronisation with your mobile phone.  The whole point of the PIM is to carry it with you – away from your computer. You should be able to read and send email, accept and send calendar invites, and add or change address book entries any time, anywhere, and those updates need to be syncronised over the air to your “home base”.

For many people, “home base” is a computer, and this doesn’t really work for over the air sync, because most people’s computers are behind firewalls or even powered off while they’re on the road.  For these people, there is nothing to sync to until they are sitting at their computer anyway, so maybe it’s not so bad to sync the phone with bluetooth or a cable “once you get back to your desk”.  Maybe this is good enough for some people.  Their data isn’t available from more than one computer, and their PIM data might not be replicated for short periods of time when they make updates to it while on the road.

For those of us who want over the air syncronisation, we use cloud services.  Our PIM data’s home base is not on our desktop computers or our phones – it’s on a server somewhere on the Internet, and it’s available all the time.  Let’s count how many companies offer services like this, and check out the general availability of their services across devices…

1. Microsoft Exchange.  Typically if you are working for some enterprise, they have an Exchange server.  Exchange uses proprietary tech for sync, but there’s alot of support for it from the smartphone market.  Even Nokia and the iPhone have Exchange sync support.  Your Exchange admin may not have enabled this support, or your Security admin may not have allowed the access through the company firewalls, but I haven’t met too many on that side of the table.  For the most part, devices that sync with Exchange keep all three datasets (email, contact, calendar) up to date with your device over the air.
2. RIM’s Blackberry.  The Blackberry is the golden child.  They made a device in the mid-90’s that very thoroughly mimicked the desktop PIM, and made syncronisation a breeze with their Blackberry Enterprise Server (BES) software, which was responsible for the syncronisation with your company’s email system (such as Exchange).  Since then, they’ve only gotten better, and now have Blackberry Internet Service (BIS), which allows individuals to take advantage of cloud syncronisation without the need for Exchange or BES – though I don’t think there’s a way to sync anything other than the Blackberry itself (such as other desktop PIM applications) with the cloud data.  But I don’t know much about it so I could be wrong.
3. Apple’s MobileMe.  From what I can tell, this isn’t so much a service that hosts your PIM data in the cloud, as much as it is simple cloud sync between devices.  Pretty cool, but also $99/year for individuals.  As with BIS, I’m not sure what you can sync to this other than the iPhone, iCal, and the Apple Address Book.
4. Google.  This includes Google Apps for Domains, as well as plain-vanilla Gmail.  Both support IMAP and POP3 for email sync, and CalDAV for calendar sync.  Unfortunately, they don’t implement any standard for contacts sync, because no standard exists (yet…).  They do have a program for syncing with Microsoft Outlook, though I haven’t tried it and don’t know whether it syncs contacts.  Zindus for Thunderbird syncs contacts with Thunderbird’s address book, and I’ve seen some other pay-for options to sync various programs with Google contacts, such as Spanning Sync 3, which is $65 one-time (and it syncs the Google calendar with iCal too).  BTW, with their maturing Android platform and cool new phones, Google’s going to give Microsoft and RIM a real run for their money in this space.  Or should I say a run for their revenue streams?

…and that’s about all.  So from a standards perspective, or in other words, something that should work with any service provider and almost any client device/software, we have IMAP for mail and CalDAV for Calendaring.  While IMAP is mature and awesome, CalDAV is both new, and sparsely and poorly implemented.  Both Thunderbird and iCal *supposedly* support CalDAV, but I’ve tried it, and it sucks.  In iCal, you can’t accept meeting invites into a CalDAV calendar, and you can’t move an existing meeting from a local calendar to a CalDAV one, or vice-versa.  This alone makes it entirely useless as a PIM solution, as I can’t get meeting invites from my email into my CalDAV calendar.  Minor oversight, there Apple.

Using Lightning for Thunderbird allowed me to accept meeting invites from email into a CalDAV calendar (note – using Mozilla’s stand-alone Sunbird does NOT, nor does it integrate with any address book whatsoever), but, erm, how do we describe this… ah – it’s FLAKEY.  It seems every time you go to add something to the calendar, you get a MODIFICATION_FAILED message, which you can only recover from by restarting the entire application.

MobileMe and BES are not options.  MobileMe is retardedly expensive.  Simple as that.  $99/year is just a ridiculous price point for sync.  BES is not an option because a) I don’t have a Blackberry, and b) my work doesn’t run BES.  They do, however, run Exchange.  So what’s wrong with that?  Why don’t I sync with Exchange?  Well, I was.  Until I ran into this one, ridiculous, annoying, impossible bug.

We have both Exchange and Gmail at work (don’t ask – why and how we have both is an entirely different topic), and I have a Mac, and an iPhone.

I run OSX, not Windows.  Although you CAN run Windows on a Mac, things just don’t work properly.  Like the webcam, and sound.  Or the mouse/trackpad.  I don’t want to run Outlook in a VM because that’s an incredible amount of overhead just for Outlook, so I run Entourage.  Unfortunately, there’s a timezone bug, so all of my meeting requests go out in UTC, meaning that they appear on non-Exchange calendars (such as Gmail) 3 hours ahead.  This is the bug, and it means I can’t run Entourage.

I can’t stand Mail.app or iCal, and even if I could, iCal and the Address Book aren’t stored on Exchange, meaning I can’t do sync of any sort.  And if I can’t sync it to Exchange, I can’t get it on the iPhone over the air – instead I have to plug the iPhone into a cable and sync over USB with iTunes.  Although I can sync ical and the Address Book with Entourage, which in turn syncs with Exchange, this means I need to run Entourage.  See paragraph above for why we won’t be doing that.

I’ve also tried Thunderbird with the Lightning Extension and Zindus – to sync the mail with Exchange and the calendar/contacts with Gmail.  THAT doesn’t work because IMAP is blocked to the outside world on our Exchange server, and because the CalDAV support in Lightning is flakey as mentioned above – even with the Google Calendaring plugin.  Which is very unfortunate because this was turning out to be a sweet, cross platform setup until I hit upon those two problems.  The other problem with this is that the iPhone only supports one Exchange connection, and Google requires you to use the Exchange connector on the iPhone for syncronising contacts and calendar over the air.

To wrap up a long and boring story, my point is that it’s surprising to me that we can be almost 20 years into the digital PIM universe, and still not have a mature framework for multi-device, over the air sync.  If anybody’s got any good suggestions, I’m all ears and game to try it out, but you can leave out the “get a different device” argument, because I’ve got what I’ve got.  And you can leave out Apple’s craptastic $99/year option too, and running a VM just for Outlook (although I might have to resort to this in the meantime, unfortunately).