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I sync my contacts / calendars via iCloud with my iPad. Could I set up another Outlook (on my Laptop) and have all three in sync - or would this mess up everything?

So e.g. create an appointment on my Desktop, sync to iCloud, and get this appointment forwarded to my laptop's outlook.

Is someone having experience with such a scenario?

Desktop <-> iCloud <-> Laptop <-> iCloud <-> iPad

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If you following Apple's instructions to set up iCloud on your PC with both your desktop and your laptop, then everything will sync nicely between Outlook on your desktop and Outlook on your laptop.

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I do not have any problems setting it up. No issues with 1 Outlook and 1 iPad. But with 2..n MS Outlooks I am not sure whether I will mess up all my contacts (e.g. double contacts, lost contacts ..) – Horst Walter Dec 18 '11 at 21:11
up vote 0 down vote accepted

Update: I am doing this for a while now. It works with one iPad and 3 Outlooks. During the setup stage I have been bothered with some cloned contacts and calendar entries, but after changing all contacts to iCloud and removing the redundant contacts manually it works fine now.

Make a backup of your calendar and contacts before you start!

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