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Hello & Welcome to JustAnswer. May i connect with you remotely to check/fix the issue directly? Thanks
What is the error you're getting and what procedure are you using to open iCloud contacts? Does the iCloud sync in real time with Outlook? Issue needs to be troubleshooted.
1. Go to Start -> Control Panel.2. Open iCloud Control Panel -> Sign out from iCloud control Panel.3. Go to Outlook -> Click on File ->Options ->Add-ins.4. Select Com Add-ins in Manage -> Click on GO.5. Disable all the Add-ins -> Click OK to save the settings.
Now go to iCloud Control panel and sign into the iCloud account. Open Outlook and check
How was it syncing with the icloud then via what?