While this article was originally when iCloud2 was introduced many, many years ago, some of the issues raised back then remain a problem today, such as messages getting stuck in the Outbox.

1. Appointment and contact notes are plain text only
2. Natural language not supported in date fields
3. The contact linking field is missing
4. Outgoing messages are stuck in the Outbox
5. iCloud error: The set of folders cannot be opened.

In some versions of Outlook and iCloud, you may be able to set iCloud data files as the default data file in Outlook. However, it is not recommended at this time and is not supported. See iCloud default data files for details.

iCloud Contacts not listed first when clicking To

If you don't see your iCloud contacts first when you click the To button, the iCloud contact folder is not set as the default list in the Address Book Options.

1. Open the Address Book using the Address Book button on the Home ribbon
2. Click Tools, Options
3. Select iCloud in When opening the address book, show this address list first

If iCloud is not listed in the Address book drop down, you need to right click on the iCloud Contacts folder, choose Properties and enable it as an Address book. See "Contacts are missing when you click the To button" for more information.

Change Views

To apply a different view to all Contact folders switch to the View tab and apply a different view to the folder:

1. Select a Contacts folder not in the iCloud
2. Switch to the View tab
3. Expand the Change views button and select Apply current view to other folders
   
4. Expand the iCloud entry and select the iCloud contacts folder
   
5. Click Apply

Additional Outlook-icloud articles are listed at the end of this article, with the newest articles at the top of the list.

Appointment and Contact notes are plain text only

The Notes field in Appointments and Contacts use plain text format in iCloud. This is "by design" due to frequent complaints about the formatting getting messed up during the sync process.

Additionally, the date fields in iCloud appointments do not support natural language. You need to type the date in full short date format (2 digit year ok).
1d does not convert to tomorrow's date
12/1 converts to 12/1/2000
12/1/12 converts to 12/1/2012

The Contact linking field is missing

The contact linking field is not supported in iCloud. This is the field at the bottom of an appointment or contact that displays linked contacts. (It's turned off by default in Outlook 2007 and up and can be enabled via the Options > Contact Options dialog.)

Outgoing messages are stuck in the Outbox

Users are reporting outgoing messages getting stuck in the Outbox after installing iCloud.

There are two causes:

iCloud is marking the messages read when you look in the Outbox. You'll know the message was marked as read by the icon - its no longer a closed envelope and is the draft's paper and pen icon instead.

The solution: stop looking in the Outbox or stop using iCloud. To resend, open the message and switch to the Inbox then click Send on the message. Do not look in the Outbox.

The other cause is just a general problem with iCloud. This usually manifests after installing updates. If this is the case, there are two potential fixes:

1. Disable iCloud, verify email sends correctly then re-enable it.
2. Move the message from the Outbox to the drafts folder or delete it. Open it from Drafts or Deleted Items then Send again.

I tried to disable iCloud using the Outlook Trust Center but it won't let me. It keeps telling me only an Administrator can do this and I am one.

You need to close Outlook. Right click on the Outlook shortcut you use to open it and choose Run as administrator. If you don't see run as administrator, hold Shift as you right click. Now you should be able to disable it. Complete instructions (and screenshots) are available at Add-in can only be Disabled by an Administrator

iCloud error: The set of folders cannot be opened.

After upgrading Windows, you may receive the following error:

The set of folders cannot be opened. The information store could not be opened.

You need to re-sync the iCloud data file. close Outlook, open the Control panel and search for Mail. Select Data Files. Select iCloud from the list of accounts then click the Settings button. Close Outlook and reopen Outlook.

Tools in the Spotlight

Companionlink for Outlook

CompanionLink synchronizes Outlook data with phones and other supported desktop applications and web-based services (like Google). Companionlink supports all versions of Outlook, including Outlook 2013 32-bit and 64-bit, and Windows 10. Version 9