Outlook 2010 PC? It’s iCloud Or Google Calendar Sync, Not Both – And Outlook 2011 Mac Gets No Love

I live a complicated Calendar life. I keep my schedule in Outlook 2010 on my PC, which syncs to the cloud through Google Calendar but can’t talk to Outlook 2011 on my Mac, which I use for travel. Can Apple’s new iCloud save me? Let’s talk platforms.

iCloud & Outlook 2010 For PC

iCloud is available to PC users, and it does work with Outlook 2010. I downloaded the iCloud Control Panel software, told it to sync with Outlook, and away it went.

After it was done, my first concern was that my Outlook Calendar was completely empty. Oh dear. Fortunately, none of my appointments were lost. iCloud had created two calendars, in a new iCloud section of Outlook.

One was for what I gather is now the new location for my calendar. The other was for conflicts that iCloud wasn’t sure what to do with.

Now, if you want the full story of how I resolved this, keep reading. If you only want some highlights:

  • You can’t create a calendar in Outlook and have that appear in iCloud
  • But you can create a calendar in iCloud and have that appear in Outlook
  • You can’t import into a calendar on iCloud

Merge Conflicts? Start Over!

The iCloud software helpfully alerted me to these conflicts, with a pop-up box promising further advice. That jumped me over to the iCloud Help home page, with no advice displayed for anything I can find when I search for “calendar merge conflicts” or “merge conflicts” or even just “merge.”

I headed over to iCloud, to see if maybe it showed both calendars there in my online view, along with a way to merge them. No. Only the main iCloud calendar was shown. Nor was there any way to import a bunch of events, that I can see. That’s something that Google Calendar supports, despite being online. It’s also something that Outlook supports. I guess if you need to get a lot of events into your iCloud calendar, you’ll have to use a software program like Outlook or iCal (I don’t use this, myself).

Over on Google Calendar, my original Outlook calendar was still active — fortunately, even though I had auto-sync on, there were so many deletions that it was asked to do (because iCloud had wiped out my original calendar on my desktop) that it asked if I wanted to go ahead. I also quickly turned sync off quickly.

This is a good time to say that before you do ANYTHING with Outlook, export your calendar. That way, you can get back to where you where, if things get messed up.

In my case, since Google Calendar still had a clean record, I exported a iCal copy (use the private address option for this; Google’s instructions are out-of-date). Then I opened that calendar using Outlook. That created a new calendar in a new group called “Other Calendars.” I dragged the new calendar into my iCloud group.

That did nothing. Apparently, if you add new calendars in Outlook, even in your iCloud group, it doesn’t care. Those aren’t going to sync. But annoyingly, if you create a new calendar at iCloud, that calendar will sync over to Outlook. That would be a good workaround, if iCloud allowed for importing. As I said, it doesn’t.

Over at the Outlook site, there was a help file that suggested there was a way to merge two existing calendars. No luck, however. Trying that, only my iCloud-based calendars were listed. There was no way to merge the new one I’d created from my Google Calendar data (or that you’d be able to merge if you created from any backed-up data).

Sigh. In the end, I found a help page on how to delete all entries in an Outlook calendar. I wiped everything off my main iCloud calendar within Outlook. That did the same online. Next, I went File > Options > Advanced > Export (yes, Export, it’s a stupid name for trying to import) > Import an iClaendar file. Then I selected my clean Google Calendar export file (or you could use any clean file) and selected Import into my existing calendar rather than “Open as New.”

And that did nothing put repopulate my old, original calendar with what iCloud had cleared out.

In the end, I turned off iCloud. I reimported my calendar into Outlook, into my main calendar, and I started all over again. And it took ages, because iCloud didn’t clear out my old calendars at first. Hint: turn it off, then make sure you sign out.

In the end, the second attempt got all of my items into iCloud and the iCloud calendar in Outlook 2010. Now it was Google Calendar sync time.

Outlook: iCloud Or Google Calendar Sync, Pick One

Why on earth would I want to sync iCloud and Google Calendar? If two clouds combine, won’t there be rain?

Why not? As I said, I really live in Outlook. When I’m traveling, I want my calendar on my travel devices. Often, that’s an Android phone. Google Calendar plays nice there.

So, I’m not really syncing iCloud and Google Calendar. I’m syncing Outlook with both iCloud and Google Calendar. Does that work? No. Oh, no it doesn’t.

I have happily used Google Calendar Sync as a lightweight way to keep Outlook and Google Calendar talking to each other. Every 30 minutes, the two talk. If I’ve made a chance in either place, they swap info. This has allowed me to always have my calendar on any device — even my iPhone.

Google Calendar Sync will only talk to your default Outlook calendar. iCloud, as I’ve explained, clears that out and makes its own iCloud calendar. That’s not the default, so Google can’t get at it. Why iCloud can’t just use the default, as Google does, I don’t know. But it means you have to make a choice.

You can sync between Outlook and Google Calendar, or between Outlook and iCloud. But you can’t do both.

Outlook 2011 For Mac: iCloud & Google Calendar Both Hate You

My real dream, since I started using Outlook 2011 on the Mac last year, was that it would be able to sync with my calendar as Outlook on the PC can. But Google has never made a calendar sync option that worked. Or Microsoft hasn’t helped. I don’t know. But you’ve been screwed.

Now Apple doesn’t care, either. iCloud has no ability to sync with Outlook 2011. There’s nothing there. Checking further on the Apple site, only iCal on the Mac is supported.

In the end, I’m kind of disappointed. In terms of calendaring, iCloud isn’t solving my cross-platform issue at all. It’s also being more invasive than the current Google solution that I’m already using, coming along and pushing my Outlook default calendar out of the scene.

Why on earth didn’t Apple support Outlook 2011 on the Mac?

It’s also bizarre that the calendar app on my iPhone itself, it merrily deals with both.

Of course, if you’re an all Apple person, iCloud calendar is probably awesome. If you’re using a PC and Apple devices, still lots of awesome. If you’re trying to use Android, staying with Google makes sense. If you do everything like me, well, you probably deserve all the pain that comes your way 🙂