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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 are listed below. Click on the links to read about the solutions.

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

If you experience any 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, follow the steps below:

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

Duplication problem

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

Other synchronization problems

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

IMPORTANT: Before you start, 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 Apple device is configured with an iCloud account.
  • You meet all of the system requirements listed on this site.
  • iCloud Control Panel / iCloud for Windows is up and running with your credentials typed in.
  • You are using CodeTwo Sync for iCloud with the default Outlook profile. 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. Be aware that during the activation our program slightly alters the Outlook Add-In installed in your system. This is very often detected by local antivirus software or the Outlook itself. Go to the list of active add-ins in Outlook’s options. The first add-in which will be turned on will be Sync for iCloud (but this is not our software, this one belongs to Apple). Most probably, our CodeTwo Sync for iCloud add-in will be at the bottom of the list as the disabled add-in. Try turning it on again. See this article on how to enable disabled add-ins in Outlook.

If you meet all of the above-listed 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 (NOTE: you may have to perform the repair a couple of times until ScanPST finds no errors in your Outlook data files)
  3. Reboot the machine which hosts Sync for iCloud.
  4. Reinstall Apple's iCloud Control Panel / iCloud for Windows (you can do this via the Windows Control Panel).
  5. Reinstall Sync for iCloud via the Windows Control Panel.

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

Diagnostic procedure

Step 1. Create a test item with C2TEST as Subject/Name on your Apple device in one of the folders you wish to synchronize (calendar, contacts or reminders). Now go to www.icloud.com and check if the test item appeared in the corresponding folder (Fig. 1).

YES, IT DID: Go to Step 2.

NO, IT DIDN'T: There is a problem in the synchronization between your Apple device and iCloud. You have to correct this before proceeding (click here for Apple Support).

271-1
Fig. 1. A Reminders/Task folder viewed via iCloud.com (click image to enlarge).

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

YES: Go to Step 8.

NO: Go to Step 3.

271-2
Fig. 2. iCloud folder tree viewed in MS Outlook 2010.

Step 3. Does the machine which hosts the MS Outlook you want to synchronize with iCloud have internet access?

YES: Go to Step 4.

I DON'T KNOW: If you accessed this article on the machine in question, then chances are it has internet access. To be 100% sure, consult your internet service provider or an IT expert.

NO: You have to fix this. If you do not know how, consult your internet service provider or an IT expert.

Step 4. Do you see the iCloud folder tree in your MS Outlook when in 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. If this does not help, look for a solution at Apple Support.

Step 5. Are you signed in to iCloud on the machine in question?

YES: Go to Step 6.

NO: Close your Outlook application. You have to correct this by going to Start, Control Panel, iCloud and signing in (Fig. 3). This did not help? Go to Step 6.

iCloud Sign in window
Fig. 3. iCloud Sign in window (click the image to enlarge it).

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

YES: Go to Step 7.

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

Step 7. Is your most up-to-date iCloud information present in MS Outlook on the machine in question?

YES: If so, and only the test item was not synchronized, you have to correct this before proceeding. Try asking Apple Support.

NO: Click the iCloud Refresh / Go online button in MS Outlook (Fig. 4). If it does not help, look for a different solution. You have to correct the problem before proceeding.

271-4
Fig. 4. The iCloud Refresh button in MS Outlook 2010.


NOTE: You can advance to Step 8 only when the test item appears in the correct folder in MS Outlook.

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

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

NO: You have to correct 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.

  • Applies to: CodeTwo Sync for iCloud Other Tools for Outlook
  • Categories: FAQ, How-To, Troubleshooting
  • Last modified: 2016-11-22
  • Created: 2012-11-08
  • ID: 271
  • Keywords: icloud, outlook, synchronization, iphone, ipad, contacts, calendar, tasks, reminders, item, diagnostics, sync, sfic
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