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Problems with iCloud and Outlook

An iCloud link with Outlook sounds great, a pity it doesn’t work in the real world.

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Lots of iPhone and iPad users got excited when they learned about iCloud and its ability to sync mail, calendar, contacts and tasks with Outlook via the Internet.

Hold the applause, if you actually try to use iCloud’s links to Outlook you’re in for disappointment and frustration.

You’re better off sticking with iTunes.

The iCloud/Outlook link is there and works so Apple isn’t outright lying. However the connection with Outlook is so proprietary and inflexible that it’s effectively useless for any existing Outlook user. has look at the Documents synchronization feature of iCloud separately.

After you’ve installed the iCloud application for Windows, you can see these configuration options.

iCloud control panel for Windows image from Problems with iCloud and Outlook at

If you want more details on the setup and workings of the iCloud program for Windows, check our detailed article.


The Mail option is usually grayed out. That’s because you need a MobileMe account from Apple to enable this option. Any other email service doesn’t qualify .. move along, nothing to see here.


Contacts can only be synced between iCloud and a specific iCloud Contacts folder it creates in Outlook.

There’s no way to make the iCloud Contacts folder the default contacts folder or ensure new contacts are saved in that folder.

You can copy/move your existing Contacts to the iCloud Contacts folder but any new contacts will go to the original contacts folder.

That means you have to keep checking to make sure any contacts are in the iCloud Contacts folder because there’s no way to do it automatically.

Calendar and Tasks

It’s the same problem here. iCloud makes new Calendar folders independent of any existing, default calendars.

You can’t change Outlook’s settings so these new calendar/s are the default location for new appointments.

The result of all this is that customers will have to check their calendar, contacts and tasks folders manually and move any new entries into the iCloud equivalents. Hardly a satisfactory solution.

Stick with iTunes

These severe limitations in iCloud with Windows are in stark contrast to the long standing method of syncing an Apple device with Outlook using iTunes. You plug your device into a computer with iTunes and it will sync all your music, apps and Outlook folders.

Unlike the simplistic iCloud version, in iTunes you can select which Outlook folders to sync. You can choose your existing calendar and contacts folders to synchronize and the choices even default to the Outlook default folders.

In other words the iTunes method of Outlook connection works while the iCloud one doesn’t, for all practical purposes.

Even better, with the latest iTunes and iOS v5 you can use iTunes to sync without the cable. The iPhone, iTouch or iPad and iTunes can sync whenever they are on the same local network.

Or use what you have

Exchange Server, Small Business Server, Office 365, Gmail and Hotmail users don’t need the iCloud service. All those mail hosts already store your calendar and contacts in a ‘cloud’ that you can connect to Apple devices using ActiveSync plus you get email connection without paying for MobileMe.

In short, iCloud is worse that useless with Outlook and there are better, cheaper ways to keep your data synchronized anyway.

Article posted: Wednesday, 26 October 2011

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