iCal vs Outlook calendar

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I run a Mac Mini ver 10.7.5, iCal 5.0.3, Mail ver 5.3, Outlook ver 14.3.4, iTunes 11.0.4(64 bit) and Office for MAC 2011.

My dilemma is that I have never been able to sync Outlook to my iPad and iPhone. I believe that iCloud is operational and setup correctly.
I tried to setup an iCal calendar but with no success.
I just want one or the other calendars to function correctly between three OS devices.

I have attempted so many things by now I have completely comfused myself.

I'm wondering if starting all over from a clean slate might help.

Please help this Apple novice!
 

Slydude

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If things have gotten that confused starting over is probably a good idea. Let's get started with a few questions:

1. You mentioned that iCloud seems to be working properly. What things have you tried to synch that seem to be working properly?
2. What happens when you try to sync a calendar using iCloud and Calendar?
3. Does synching work if you synch using a USB cable?
 
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Hi Slydude,

1. I guess nothing works as I have tried to sync the iPad and the iPhone and nothing comes over.
2. When I USB sync either device the info content tells me that Contacts and Calendars are syncing via iCloud.
3. See 1 and 2.

I really don't know what I'm doing.
 

Slydude

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Give this setup walkthrough a quick read. The process should be essentially the same for iPad and iPhone. If that does not work post back with results and we'll try and straighten things out.
 
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When I switched to Apple from Windows couple of years ago I had used Outlook for years and was stuck on thinking I should keep at it. Tech support helped me through migrating my data, which was tricky, but synching was challenging. Then I simplified my life a lot by abandoning Outlook and using the Apple apps instead. You might have reason to persist with Outlook, but that's an option to think about. My old Outlook data is still there if I need to look into it, but i've rarely had the need. I do miss the all-in-one convenience of Outlook, but not enough to try again.
 

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