The iPhone Calendar Conundrum

The iPhone calendar has proven a tough nut to crack, as my many attempts to get my work calendar onto the device have fallen short.

As I reported earlier this month, the iPhone is hardly the ideal device for corporate users. However, the device inspires a lot of love, and over time, will likely engender a lot of creative thinking that will get it up to speed.

Even now, with its mostly-full featured browser, there are many ways for the savvy user to work around the device's current limitations, but one application - the calendar - is proving a tough nut to crack.

At home, I sync the iPhone at home on my media and gaming PC. The only work-related things I need to access on the iPhone are e-mail and the calendar applications on our corporate Exchange server. I've kludged together a suitable way to access my work e-mail in a way that works for me, but finding a way to access my work calendar on the iPhone, in a way that I can effectively use, has thus far proved elusive.

I've maintained a few rules in my quest to outfit the iPhone for my work needs. First of all, I will not ask our IT department for anything... no Exchange add-ons, no third-party solutions like Synchronica, no nothing. I am treating it like an outlaw device at work, so I can only use the resources I have at hand (which thankfully, is more than the average worker I think.)

Second, I will not install iTunes on my work PC under any circumstance. I have a limited amount of storage, processor and memory to work with on my work PC and I don't need to muck that up with a bloated pig of an application like iTunes. Not to mention that all of my media files are at home and the iPhone and the iPod are designed to synch with one computer only.

I actually like the iPhone's calendar application. The on-screen visual dials the device utilizes to input dates and days of the week are visually cool, and they are easy to navigate with my fat, greasy fingers. They vaguely remind me of a Vegas slot machine, which makes me mildly happy.

But since I can't sync that calendar to anything, I am willing to look at Web-based alternatives instead.

I first tried to access my work calendar via Safari and OWA (Outlook Web Access), figuring I could hopefully just leave that page open for quick access. The cramped Web interface that Exchange 2000 provides for non-IE clients is passable for viewing the schedule, but far from ideal for creating new entries as it requires a lot of precision finger work and screen resizing. But worse, the connection would occasionally hang—presumably while awaiting authentication—and I don't want to have to enter my Exchange credentials into Safari every time I want to look at the calendar.

Then I started looking into syncing the calendar with one of the many hosted e-mail vendors I utilize on a day to day basis. I landed on Plaxo 3.0 as a valid way to upload my Exchange calendar to Google or Yahoo. But even that did not work as I had hoped.

With Gmail, I actually host my own domain via Google Apps. Unfortunately, Plaxo does not support Gmail-hosted domains at this time, only regular accounts ending in Gmail.com. I found that this meant I could sync my existing Google calendar entries into Plaxo, but not vice versa. So I could not import my work schedule all the way to my Google domain.

I suppose I could create a new Gmail account, synchronize it with Plaxo (and therefore my Exchange account), then share the Gmail calendar with my hosted Google domain account, but that seems pretty kludgy. And to be honest, I don't really like the Google Calendar enough to be sure it is worth the trouble.

The problems with Yahoo were a little different. I have a regular Yahoo account that I primarily use for Fantasy Basketball (at which I generally rule—3 wins in 5 years!) I don't really use that e-mail account anymore, and I never used the Yahoo Calendar before the iPhone. But playing around a little bit, I decided the application would be an acceptable compromise.

I easily synced Yahoo calendar with Plaxo, but then the problems started. Yahoo Calendar comes in two flavors, the new AJAX (Asynchronous JavaScript and XML)-based beta and the older version. Of course, I prefer the new one. But the new one does not support the Safari browser (which the iPhone uses), so my only recourse was to use the old calendar. Yuck.

Unfortunately, I can't fall back to simply using Plaxo's Web calendar either, since that also does not support Safari right now.

At this point, I think my only recourse is to install Outlook on my PC at home, and to use Plaxo to synchronize with my work account. This solution should work, but then the drawback becomes one of convenience. I make changes to my calendar quite frequently, and almost all of these changes are done in the office. I feel that not being able to synchronize the iPhone until I get home every day would ultimately be an unsuccessful course of action.

So I ask, how are other people who are getting around the current limitations of the iPhone calendar? Has anyone come up with a decent workaround for a calendar kept on a PC other than the iTunes sync box?

It seems to me that Apple could really help its users out by uncoupling data and media synchronization, thereby allowing users to synchronize different data sets from multiple PCs. Of course, I still don't want to install iTunes at work (nor, do I imagine, IT wants me to do this), so I would also need a lighter weight sync application. And I don't see this happening unless DVD Jon has something up his sleeve.

Perhaps a more likely alternative would be for Apple to open up their .Mac service a little bit in order to cater to Windows users. Offer buyers of the iPhone a year or six months of free service for full .Mac capabilities. (After all, we did just drop 5 or 6 bills on the thing, so loosen the purse strings Apple.) Or give iPhone customers free or cheap calendar, contact and bookmark storage and synchronization, which should be fairly light on the storage and transfer side of things.

Apple would then need to offer a lightweight Outlook plug-in (a la Plaxo) to allow customers to easily upload from Outlook (or other applications) to .Mac and to add the ability to the iPhone for the calendar to do a Web-based data pull to retrieve the data from the .Mac account.

Mac purists may scoff at these suggestions and simply say that we PC users should just get a Mac for these options. But we need to remember, this a work decision (not a personal one.) And let's face it, Windows users drive the lion's share of Apple's newfound success. Does anyone out there think the iPod would be nearly as successful as it is now if Apple had not opened it up to Windows users a year or so after the product first launched?

If Apple wants to get the iPhone to achieve its anticipated success in the long run, Apple will certainly have to cater more to PC users; at least to the ones willing to shell out the cash for the device who will then take it into the enterprise, with or without IT support.