If all your content synced correctly, the issue is likely related to the specific user account your are trying to sync. If your content didn’t sync as expected, try running the "i Phone/i Pod touch sync" test using i Tunes Diagnostics while your device is connected to i Tunes. If your data still doesn’t sync with the new user, apply the steps for system-wide issues.
Instead of syncing, you can opt to replace all contact or calendar data on your i OS device with the data in your Outlook profile.
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As of the i Cloud 5.1 update, which was released at the end of 2015, i Cloud supports Outlook 2016, 32 and 64 bit as well as Windows 10.
If you're having issues syncing using i Tunes on your PC, consider setting up i Cloud for Windows instead.
It is the simplest way to keep all of your contacts, calendar, notes, and documents up to date across all of your devices.
i Cloud helps you manage your contacts, calendars, and notes automatically so that you can access them where and when you need them.
With i Cloud, you can access your contacts from your i Phone, i Pad, i Pod touch, computer, or at i
If you prefer to sync using i Tunes, then follow the steps below to resolve the issue.
Run the ‘i Phone/i Pod touch sync test’ using i Tunes Diagnostics while your device is connected to i Tunes.