A client using Outlook 2010 wanted to sync messages he sent using his iCloud account on his iPhone with Outlook. Because iCloud (including me.com addresses) use IMAP, it should work. It didn't so he called Apple support. Apple told him it was not possible to sync Outlook sent items to the iCloud server. I showed him how to do it.
Outlook 2013 should pick up the Sent Messages folder automatically and use it instead of Sent Items folder.
iCloud users who want to sync their sent items with Outlook 2010 or Outlook 2007 will need to configure Outlook's Sent folder to use iCloud's Sent Messages folder for sent items.
Step 1: Subscribe to the Sent Messages folder
The Sent Messages folder is not subscribed by default, you'll need to do this step first. Right click on one of the folders in the iCloud folder list and choose IMAP folders....
- Click Query to list all of the folders on the server.
- Find and select Sent Messages folder.
- Click Subscribe.
- Click Ok to exit the dialog when after selecting and subscribing to the desired folders.
Step 2: Select the Sent Messages folder in Account Settings
- Open the Account Setting dialog. This is on the File tab in Outlook 2010 and on the Tools menu in Outlook 2007.
- Double click on the iCloud IMAP account.
- Click More Settings button.
- In Outlook 2010, click on the Sent Items tab; in Outlook 2007, click on the Folders tab.
- Select the option to Choose an existing folder... in
- Select Sent Messages folder.
- Click Ok and return to Outlook.
Within a few minutes, the messages you sent from your iPhone should sync to Outlook. Messages you send in Outlook will be available on the iCloud.
Sent messages aren't syncing
If the messages aren't syncing between Outlook and the iCloud, you need to check settings on the device. Open Settings, select iCloud on the left, then select the account on the right. Select Advanced, then Advanced again on the next dialog. The final dialog lists the folder the iCloud is using for it's special folders. Outlook needs to be using the folder that is assigned to the Sent Mailbox.