iCloud and Microsoft Outlook

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How to sync Outlook to your Apple devices with iCloud and why it sucks.

Apple’s iCloud service provides a way to synchronize some parts of Outlook with your Apple iPhone, iTouch or iPad but it doesn’t work as most people would like.

Before iCloud, you could synchronize your Outlook Contacts, Calendar and Tasks via iTunes. Whenever you plugged your device into the iTunes enabled computer, details would be exchanged between the device and Outlook. This is clumsy, somewhat unreliable and slow. However it worked as people would expect because it linked existing Outlook folders with the Apple device equivalent.

Now with iCloud the synchronization can happen automatically whenever Outlook is running and the device is on the Internet via Wifi. However it links with special ‘iCloud’ folders in Outlook not the default folders most people use. This is a serious limitation that makes the promised Outlook synchronization almost worthless.

You might decide that the benefits of iCloud are not enough to make up for the inconveniences.

We’ve looked at iCloud’s document synchronization (such as it is) separately.

How it works

Outlook Calendar, Contact and Tasks information from an ‘iCloud’ set of folders is synchronized with the iCloud service on Apple’s servers.

From there it is synchronized with any Apple device you have. New or edited items made on the devices are replicated back to the iCloud storage and from there to Outlook and other devices linked to that account.

As a bonus, you can view or edit Calendar, Contacts, Tasks from any web browser.

Alas, as we’ll see, the integration doesn’t work as you’d like or expect.


To get started with iCloud on Windows you need:

  • Windows XP with Service Pack 3 or Windows 7
  • Outlook 2007 or Outlook 2010

(If your Outlook is connected to Exchange Server, Small Business Server or Office 365 then you don’t want to use this iCloud feature. That’s because Exchange Server already acts as a central store for all your Outlook data which can be accessed from Apple devices as well as web browser. Ask your network administrator for setup details.)

For the rest of us, you need the new iOS v5 which is a free update for iPhone (3GS, 4 and 4S), iPod touch (3rd or 4th generation) plus all iPads (1st or 2nd generation). It’s installed via iTunes and may take an hour or more to complete.

During the device setup for iOS 5, turn on the iCloud option when prompted, or go to Settings and customize it at any time. For the purposes of this article you’ll need the ‘ Contacts ‘ ‘Calendars’ and ‘Reminders’ options ON.

1619 iCloud   sync settings on iPad - iCloud and Microsoft Outlook

It works with 32-bit or 64-bit Outlook.

iCloud for Windows

For Windows Vista SP2 and Windows 7 users only there is an iCloud Control Panel free download available.

This gives you access to some iCloud features like mail, calendar and contact sync.

All this is controlled from an iCloud item in the Windows Control Panel.

1619 iCloud configuration on Windows control panel - iCloud and Microsoft Outlook

Choose the ‘Contacts’ and ‘Calendars and Tasks’ options then click Apply.

You’ll need to close Outlook during the setup or the setup will do that for you.  As usual, be careful to ensure that Outlook has really closed and not just invisible.

1619 iCloud setup   reminder to close Outlook - iCloud and Microsoft Outlook

When you restart Outlook you’ll see a new set of folders under an ‘iCloud’ heading.

1619 iCloud folder list in Outlook - iCloud and Microsoft Outlook

These are additional folders to the default ones you regularly use. There are two calendar folders ‘Home’ and ‘Work’. Tasks folder is called ‘Reminders’ while Contacts is another contact folder.

It is these folders that are synchronized with iCloud and your Apple devices – not the default folders where, most likely, you store all your information.

The sync does work well and, after any initial rush of data exchange, will update a folder in seconds so the same information appears in Outlook, on the web and a device respectively.

1619 iCloud contacts in Outlook - iCloud and Microsoft Outlook

1619 iCloud contacts in web interface - iCloud and Microsoft Outlook

1619 iCloud contacts on iPad - iCloud and Microsoft Outlook

There is a ‘Refresh iCloud’ button added to Outlook but we didn’t find it necessary since any changes appeared on our test device within seconds.

iCloud Web Interface

You can see contacts, calendar and reminders saved in the iCloud online storage from any web browser. Go to icloud.com and login using your Apple ID.

These are the default icons which appear whether you have those parts of iCloud enabled or not.

1619 iCloud   main web screen - iCloud and Microsoft Outlook

Reminders are shown in the right-hand column of the calendar view.

1619 iCloud   Reminders segment in Calendar web view - iCloud and Microsoft Outlook

In Outlook and on devices the Reminders have their own icon and display

make it work

Now you have all these extra iCloud folders in Outlook how can you make it all work with your existing data? It is clumsy but possible.

The important thing is to remember to use the iCloud folders instead of the folders you’re accustomed to using. You can’t delete the default Calendar, Contacts and Tasks folders so they’ll always be there and you have to learn to ignore them (I said it was clumsy).

All your existing contacts can be copied or moved to the iCloud Contacts folder. The same with moving Tasks to iCloud’s Reminders.

(It’s best to move the items so you don’t get two folders with the same items and then the risk of confusion about which one to update. On the other hand, there’s a small risk of data loss when there’s only one copy of your vital details. Cautious computer boffins will make a safe copy of the calendar, contact and task info into backup folders ‘Before iCloud’ before making the move).

For the iCloud calendar, Apple defaults to having two calendars (Home and Work). Apple calendars have an ‘overlay’ option to show multiple calendars in the same view – a feature that Microsoft belatedly achieved in Outlook 2010.

You can use that home/work split if it suits you and move your Outlook appointments into the two Apple calendars according to their type (personal or business).

An alternative is to create a new calendar in iCloud – maybe called ‘All’ and move all the Outlook appointments into that folder. iCloud will sync the new calendar folder just like the default ones (you can delete the empty Home and Work calendars if you wish).

What’s missing

It would be much better if the Outlook integration allowed users to nominate which folders were synchronized. This would allow Outlook users to work with their standard folders and standard views while retaining the benefits of iCloud synchronization.

There’s no reason for this except expediency. Apple devices have better sync capabilities when cabled connected to a computer with iTunes running. In iTunes you can nominate which Calendar and Contact Outlook folders are to be synced. iCloud doesn’t give you that elementary choice.

It seems Apple has taken the easiest and cheapest development approach that allows them to promote ‘Outlook compatibility’ with iCloud. It’s only when the customer tries to use this compatibility that they find it’s not all it could be or even similar to the iTunes option already available.

Office users will be familiar with the ‘box checking’ marketing trick because Microsoft has done it many times. Apple is supposed to do better than that.

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