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iCloud - Outlook synchronization diagnostics

Problems after Windows or Outlook upgrade/update or program does not work at all:

If you experience problems after upgrading or updating your system or Outlook, for example you have just upgraded your Windows 8.1 to Windows 10 or Outlook 2013 to Outlook 2016 please follow the below steps. Also, if your Sync for iCloud does not work at all please do the following:

  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 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 Sync for iCloud (you can do this via the Windows Control Panel).

Duplication problem:

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

Other synchronization problems:

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

IMPORTANT: Before you start, make sure that:

  1. 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.
  2. Your Apple device is configured with an iCloud account.
  3. You meet all system requirements listed on this site.
  4. iCloud Control Panel / iCloud for Windows is up and running with your credentials typed in.
  5. You are using Sync for iCloud with the default Outlook profile. Sync for iCloud works only with the default Outlook profile - this limitation is caused by Apple's iCloud Control Panel / iCloud for Windows.
  6. CodeTwo Sync for iCloud Outlook addin is not disabled. Be aware that during the software activation our program slightly alters the Outlook Add-In installed in your system. Very often this is picked up by local anti-virus software or Outlook itself. Please 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 in the bottom of the list as the disabled add-in. Please try turning it on again. See this article on how to enable disabled addins in Outlook.

If you meet all of the above listed requirements and the problem is still present, apply the following solutions in this order (check for the issue after each step):

  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 find 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 (you can do this via the Windows Control Panel).

IF, DESPITE APPLYING THE ABOVE SOLUTIONS, THE PROBLEM PERSISTS, BEGIN THE BELOW DIAGNOSTIC PROCEDURE.

Step 1. Create a test item with C2TEST as Subject or 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 synchronization between your Apple device and iCloud. You have to correct this before proceeding (Apple support click here).

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 correct this. If you don't 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 doesn't 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: Please close your Outlook application. You have to correct this by going to Start, Control Panel, iCloud and signing in (Fig. 3). Didn't help? Go to Step 6.

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

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

YES: Go to Step 7.

NO: Apply this KB article. If this doesn't 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 didn't go through, there is something very strange going on. You have to correct this before proceeding. Apple support.

NO: Click the iCloud Refresh / Go online button in MS Outlook (Fig. 4). If it doesn't 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 with the test item with another folder in your MS Outlook (let's 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: 2016-01-15
  • Created: 2012-11-08
  • ID: 271
  • Keywords: icloud, outlook, synchronization, iphone, ipad, contacts, calendar, tasks, reminders, item, diagnostics, sync, sfic
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