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Issue 10.2 ('Assumption Approach')
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iCloud Contacts and Calendars

Issue: 10.2 (January/February 2012)
Author: Dave Mancuso
Article Description: No description available.
Article Length (in bytes): 6,682
Starting Page Number: 20
Article Number: 10205
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The day iCloud came out, I moved my contacts and calendars from Google. I didn't have an issue with Google apart from one minor issue. I just wanted to see how well iCloud would mesh with my MacBook Air, iPad 2, and iPhone 4S. And I wanted the automatic backup, music, and data synchronization features. I wasn't disappointed, until I repeated the process on my Windows 7 machine. That's where the luster of iCloud turned into a tarnished mess.

Macintosh Installation

On my Mac, I simply set the iCloud System preference pane to synchronize Contacts, Calendars, Bookmarks, etc. The only selection I left off was Mail and Notes. Since my Mail is already set as IMAP and Exchange, I didn't need to sync it. I would've liked to sync Notes, but iCloud won't do this unless you make a me.com email address. I didn't need or want one.

I've had to set iCloud settings on each device to be congruent: laptop, iPhone, and iPad. I'm not sure why iCloud can't do this for me, perhaps just asking me for authorization on each device. I've also seen client setups where the iCloud accounts are incorrect, or where the client set up a me.com account and became confused when trying to buy songs on the iTunes store with the me.com Apple ID instead of their original Apple ID. It can become confusing and annoying to correct this issue.

Windows Installation

Other than theses issues, using iCloud on a Mac seems to be a successful solution. The PC was different. First, Windows XP won't install the iCloud control panel. It needs Vista or Window 7, although I located instructions to shoehorn iCloud into a Windows XP laptop.

I wanted to set things up so that I could easily share my Calendar and Contacts between my Windows 7 laptop, my iPad, and my iPhone. I set up my GMail account as an "Exchange" account on both mobile devices. On the PC I had Outlook 2007 (a later look at Outlook 2010 gave the same results). The free Google sync calendar plugin syncs the Outlook calendar with my Google calendar account, but this didn't take care of syncing my contacts.

iCloud Contacts

I decided to move my Contacts to iCloud. This worked well and I've had no issues with it, other than having to set Outlook to use the iCloud Contacts for email address lookups. It was annoying that iCloud made its own Contacts address book instead of using Outlook's regular address book, but it's not a huge issue.

iCloud Calendar

If you use Google Calendar sync with a calendar of any significant size, it will soon begin to fail sporadically, and in fact can wipe out your entire calendar (luckily I make several backups of my Outlook data in .pst files regularly), so I decided to use iCloud for Calendar sync. It installed easily, but the first sign of trouble was that my Outlook calendar disappeared—every event was wiped clean and the calendar was empty. iCloud makes its own calendar and imports all the events from the old calendar, but until you realize this you have some heart-stopping moments. More on this later.

The second sign of trouble was that iCloud failed to import calendar events from my old calendar where someone else invited me to meetings. Since I was not the event organizer, iCloud wouldn't automatically accept the event. I had to manually drag each and every one of these events from the old calendar to the new one. That took a few hours, but it seemed to work. Unfortunately, when you do this, iCloud feels the need to send event updates to every attendee on every manually dragged event. Without telling you. Colleagues got event updates for current meetings but also for meetings up to six years in the past, which looked embarrassingly unprofessional. It's an unacceptable issue to do this without informing the user.

The other issue was that Outlook doesn't like to use calendars that aren't its main calendar. For instance, the Outlook Reminders pane on the right side of its main window shows your upcoming appointments for the day. Unfortunately, there is no way to force Outlook to use the iCloud calendar for the Reminders pane. The Reminders pane is rendered useless, informing you that you have no upcoming events. There were other minor issues, but it was obvious that Outlook couldn't handle how the iCloud calendar was set up. This was made worse by the fact that iCloud's predecessor MobileMe had no such issue. It used the main Outlook calendar. New functionality is fine, but taking away functionality is a sure way to incense users.

Google Calendar Redux

I decided to go back to Google Calendar, but I didn't trust the Google Sync plugin. I moved to a paid application called gSyncit which worked solidly. I turned off iCloud calendar sync, although to get it out of Outlook I had to remove iCloud completely and then reconfigure it to sync only calendars.


iCloud seems to work well with a Mac setup and for Contacts with a Window configuration, but I think the best solution at the moment is to keep calendars out of iCloud on the PC side. It's obvious that iCloud needs work—the issues detailed above are simply unacceptable. For this reason, it only rates a 2.7 out of 5.0. I look forward to the next revision of iCloud.

End of article.