Outlook 2010 won't sync with iCloud on the web

Outlook 2010 Calendar syncs with the iCloud Calendar in Outlook. Both are visible in Outlook, both are ticked. Calendar Sync is set up in iCloud Control Panel 2 and on settings on my iPhone & iPad. However, appointments don’t show in iPhone, iPad or iCloud on the web.

Here's what I've discovered: Outlook has two "versions," one for iCloud and one that is an Outlook data file ("My calendar"). You can check a box in Outlook to enable either of them (go to the Home tab and expand the navigation pane). The iPad does not sync with the Outlook data file. Anything entered there has to be manually copied to the iCloud version of Outlook in order to sync with iPad. So, to sync with iPad you have to uncheck "My calendar" in Outlook and then check "iCloud" and use that version of Outlook. But when I use the iCloud version, Outlook will not accept appointments sent to me by clients. It also screws up my communication with clients in other ways. So using the iCloud version of Outlook does not work for me.
I've discovered a third-party software that seems to solve this issue: Code Two Sync for iPad. You can Google it for reviews, the download link, etc. I downloaded and installed it and it immediately copied (synced?) all the appointments in the Outlook data file version of Outlook ("My calendar") to the iCloud version and synced them with my iPad. There were a bunch of duplicates, but I think there's some way to fix that. However...it also crashed Outlook on my computer (I have an older computer that is having issues). So I needed to uninstall it. I repeat, this is because my computer has been having other issues, I don't think it is the software's fault. I may try it again when I have more time to troubleshoot. Anyway, you might try this software and see if it works for you.

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    Hi guys, the basic summary is that after upgrading from a mobile me account to icloud (using a me.com account), I was able to sync everything from Outlook to the customer's iPhone but anything created after that would not sync. I tried creating a contact, calendar item, and other calendar items, none of which showed up either way (outlook to phone and vice versa).
    Here are all the details that may be needed to assist with this question (and thank you!)
    The account was upgraded from mobileme to iCloud, then outlook was upgraded from 2003 to 2010.
    OS is Windows 7 64 bit
    Outlook has 2 data files which hold all the contacts/calendars/tasks.
    I had to add the me.com email to outlook so that it would perform the initial sync.
    After the initial sync, all calendars, contacts, etc were moved to deleted items (which I think may be normal). I just moved them back to one of the pst files.
    At this point, creating an item in any calendar, or creating a contact does not result in that contact/calendar entry showing up on the iphone (or vice versa).
    Outlook does not show "icloud" calendar, only the calendars I previously created, but the iPhone says "All iCloud Calendars" and they list the calendars that we created in outlook.
    Customer says it synced fine when he used mobile me back in the day, and then it stopped so we had to upgrade to iCloud. Any ideas? =/ I spent over an hour trying to figure this one out, even had some brief apple tech help.
    Thank you SO much for your help. I'd LOVE to be able to get this fixed, otherwise I need to start looking into alternatives for syncing iphone with outlook 2010

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