On November 8, I described how a brand-new MacBook Air had made its appearance in the IT lineup for the Redmond household and some initial teething problems that this Windows-centric (to date) individual had experienced in setting up this beautiful piece of equipment. It seems that the latest HP Envy range bears a resemblance to the MacBook but I see no equivalent there for the MacBook Air.

Two weeks later on things have settled down and the major obstacles to a happy user have been removed. Printing to our faithful HP C6180 works now (albeit with more intervention than I’d like and certainly more than I expected) and I have managed to make the iPhone synchronize its calendar with Outlook. In my naivety, I assumed that anything that ran on an Apple platform would play nicely together. I was further lulled into a false sense of security about how well Outlook 2010 for Windows works (now) with iTunes to synchronize its data to an iPhone. Therefore, when I set out to configure synchronization between Outlook 2011 for Mac and an iPhone (3GS running IOS 5), I thought that this would take just a few moments. Of course, I was dead wrong.

Part of the problem is that I ignored the simple solution, which is to use over-the-air (OTA) updates whenever possible. My feeble excuse is that the previous configuration of Outlook connected to Hotmail didn’t support OTA updates whereas the new configuration for my wife’s email is Outlook connected to Exchange Online/Office 365, which absolutely does support OTA updates. There’s simply no need to get iTunes or Mac Sync Services or iCal or anything else involved. All I had to do was to configure the entry for the Office 365 mail account on the iPhone to synchronize the calendar and that was that. All done. Works without a problem. Take one more item off the list.

Although I feel a tad silly that I didn’t figure the solution out quicker than I did, I plead a certain amount of ignorance for the Mac platform and offer evidence that I consulted with two other MVPs who have some expertise in this area. After some to’ing and fro’ing via email, William Smith decided that it was time to post something definitive on the topic and he wrote the splendid blog post all about how to synchronize Outlook for Mac calendars and contacts to an iPhone. From my perspective, the most important piece of advice was:

“Exchange users have the luxury of being able to synchronize their information across multiple computers and devices wirelessly and I’d advise they stick with that. No matter what I advise they never sync Exchange data directly from computer to iPhone or else they risk duplicate data appearing as a result of the two methods of syncing.”

What else have we learned in the last couple of weeks. Well, one thing is for sure, as Paul Robichaux says “Outlook isn’t Outlook” when it comes to comparing Outlook 2010 for Windows and Outlook 2011 for Mac. Sure, email works just fine and most of the standard operations that you’d expect from a modern email client work as they should. However, there are some small things that just bug me.

First, the fonts. Now, I know that Macintosh computers have a long and noble history in the elegant use of fonts and typefaces but really, couldn’t Microsoft have worked out how to make Outlook 2011 for Mac display messages that originate from Outlook 2010 for Windows slightly more impressively than they do now? William tried to explain the reasons why to me, which basically come down to the lowest common denominator argument. Outlook for Windows sends a nicely formatted message to an Outlook for Mac user and the Mac client can’t handle the formatting sent from its Windows cousin, so it uses some other font. Jeez…

William’s advice to me was:

“If you stick with the Windows Office Compatible fonts (Format menu –> Fonts –> Choose –> Collection column –> Windows Office Compatible) you should have pretty good luck with fonts in HTML formatted messages. These are cross-platform. Likewise, your Windows counterparts must use these as well.”

The basic Calibri font seems to work acceptably but you’ll probably have less success with others, unless both platforms agree. Oh well.

My second gripe is about calendar sharing. When you view multiple calendars with Outlook 2010, the calendars are viewed alongside each other. This makes it very easy to see what appointments and meetings belong to what user. But Outlook 2011 for Mac merges everything into one calendar. Cue immediate confusion as duplicates pop up all over the place because an item is in multiple calendars. Not good at all.

I also don’t like the way reminders appear in Outlook for Mac. In Outlook for Windows you get the opportunity to postpone a reminder for another 15 minutes, 30 minutes, 2 days or whatever. The Mac version of a reminder sits there until it’s dismissed or you click on “Snooze”… in which case the reminder seems to sleep for 5 minutes. There’s a little down arrow by the Snooze button that looks like you should be able to change that sleep time but  Outlook doesn’t seem to want to play. It’s all rather weird and begs the question whether the two Outlook teams even communicate? After all, given that Outlook first appeared in 1997, you’d think that some cross-pollination of ideas might happen. And while I’m on that point, why can’t Outlook for Mac handle conversations in the same reasonably intelligent manner as Outlook for Windows, including the ability to ignore a conversation and clean up a conversation?

Another issue is that no access is possible to an archive mailbox because Outlook 2011 for Mac doesn’t support this feature. I’ve already discussed this issue before as Outlook 2011 is not the only Microsoft client to ignore archive mailboxes.

Switching platforms and clients is never seamless and two very different philosophies exist across Windows and Mac. I’m sure that other gripes will occur over time but in the meantime it’s fair to say that the MacBook Air is a delight, especially its speed and ability to resume in an instant in a way that I have never seen from a Windows PC. Oh well, I’m sure that Microsoft will improve system startup and resume operations in Windows 8 but until then it seems like Mac has a real and measurable advantage here.

– Tony