How to troubleshoot problems with iCloud - Outlook synchronization

Problem:

You experience various problems with synchronization between Outlook and iCloud.

Solution:

The synchronization failures can happen in various scenarios. The most common issues are listed below.

If the described solutions do not work, or you experience other synchronization problems, follow the diagnostic procedure.

Problems after upgrading/updating Windows or Outlook, and situations when CodeTwo Sync for iCloud does not work at all

If you experience synchronization problems after upgrading or updating your Windows or Outlook (for example, you have just upgraded your Windows 8.1 to Windows 10, or Outlook 2013 to Outlook 2016), follow the steps below. This solution also applies if your CodeTwo Sync for iCloud does not work at all.

  1. Go to your iCloud Control Panel / iCloud for Windows and log out from iCloud.
  2. Log in to your iCloud account.
  3. Restart Outlook.

If the above does not help, you need to:

  1. Close your Outlook.
  2. Reinstall iCloud Control Panel / iCloud for Windows (you can do this in the Windows Control Panel).
  3. Reinstall CodeTwo Sync for iCloud via the Windows Control Panel.

Duplication of synchronized items

If you experience duplication of items, you might need to review your settings for all of the devices that sync with your iCloud account. For example, if all your computers, phones, and tablets synchronize the same contacts with your iCloud account, you might get duplicates - this depends on the iCloud settings. In some scenarios, you will probably always experience duplication (e.g. when you created an identical contact on several different email accounts, and you sync all of these accounts to iCloud). Outlook is not able to recognize duplicates, and neither is CodeTwo Sync for iCloud. In such a case, you need to remove duplicates manually or use a third-party product to help you delete or merge duplicates. Be aware that such tools may not be free.

The diagnostic procedure

If items are not synchronized between your iPad/iPhone and your Outlook, perform the steps below to figure out where the problem lies.

Before you start

Before you begin the diagnostics, make sure that:

  • you have the latest versions of iCloud Control Panel / iCloud for Windows and CodeTwo Sync for iCloud installed on the Windows machine you are synchronizing;
  • your mobile Apple device is configured with an iCloud account;
  • you meet all of the system requirements listed on the website of our product;
  • iCloud Control Panel / iCloud for Windows is up and running, and it uses your credentials;
  • you are using CodeTwo Sync for iCloud with the default Outlook profile (learn more). CodeTwo Sync for iCloud works only with the default Outlook profile. This limitation is caused by Apple's iCloud Control Panel / iCloud for Windows;
  • CodeTwo Sync for iCloud Outlook add-in is not disabled. To check the add-in's status, go to the list of active add-ins in Outlook’s options. Note that the first add-in which is turned on is Sync for iCloud, but this is not our software - this is the Apple's add-in. Find the CodeTwo Sync for iCloud add-in. If it's disabled, try turning it on again. See our article on how to enable disabled add-ins in Outlook.

If you meet all of the above requirements and the problem is still present, apply the following solutions in the exact order provided. After each step, check if the issue is solved.

  1. Restart Outlook.
  2. Use ScanPST to repair your Outlook data files as per these guidelines (you might need to perform the repair process a couple of times until ScanPST finds no errors in your Outlook data files).
  3. Reboot the machine where Sync for iCloud is installed.
  4. Reinstall Apple's iCloud Control Panel / iCloud for Windows (you can do this in the Windows Control Panel).
  5. Reinstall Sync for iCloud via the Windows Control Panel.

The procedure

If, despite applying the solutions above, the synchronization problem persists, begin the diagnostic procedure.

Step 1.
On your Apple device, create a new test item in one of the folders you wish to synchronize (calendar, contacts, or reminders). Now check if the item appears in the corresponding folder on www.icloud.com.

YES, IT DOES: Go to Step 2.

NO, IT DOESN'T: There is a problem with the synchronization between your Apple device and iCloud. You need to fix this before proceeding to Step 2 (consult Apple Support).

Step 2.
Did the test item appear in the corresponding folder in the iCloud folder tree in your MS Outlook?

YES: Go to Step 8.

NO: Go to Step 3.

Step 3.
Do you have internet access on the machine where you want to synchronize Microsoft Outlook with Apple iCloud?

YES: Go to Step 4.

I DON'T KNOW: If you accessed this article on the machine in question, then it most probably is connected to the Internet. To be 100% sure, consult your internet service provider or an IT expert.

NO: You need to have an internet connection. If you do not know how to enable internet access, consult your internet service provider or an IT expert.

Step 4.
Do you see the iCloud folder tree in your MS Outlook in the Folder list view?

YES: Go to Step 5.

NO: Make sure that iCloud Control Panel / iCloud for Windows is correctly set up on the machine, as described in this article. If you still don't see the iCloud folder tree, look for a solution at Apple Support.

Step 5.
Are you signed in to iCloud on the machine where you synchronize Outlook with iCloud?

YES: Go to Step 6.

NO: Close your Outlook. Go to Start > Control Panel > iCloud and sign in. If this does not fix the problem, go to Step 6.

Step 6.
Do you see the iCloud's Refresh / Go online button in your Outlook?

YES: Go to Step 7.

NO: Follow this Knowledge Base article. If this does not help, look for a solution at Apple Support.

Step 7.
Does your Outlook show the most up-to-date information from iCloud?

YES: If so, go to Step 8. If everything is up to date except the test item (the item has not been synchronized), you need to fix this before proceeding. Try asking Apple Support.

NO: Click the iCloud Refresh / Go online button in MS Outlook. If it does not help, look for a different solution. You need to solve this issue before you proceed.


You can advance to Step 8 only when the test item appears in Outlook.

Step 8.
Is CodeTwo Sync for iCloud configured to synchronize the iCloud folder that contains the test item with another folder in your MS Outlook (let us call it the target folder)?

YES: Repair the MS Outlook data file that hosts the target folder using SCANPST as per these guidelines.

NO: You need to fix this before proceeding. Right-click the iCloud folder, select Sync with Outlook and navigate to the target folder. If this does not resolve the test item synchronization issue, use SCANPST as explained above.