iCloud 5.1 has solved the problem for me!
As the first post indicated, I had the problem where I’d get a windows pop-up that said to Repair iCloud installation, then Restart.
I downloaded the update. Restarted my machine. Upon restarting, iCloud opened without an error message. I checked the box for Contacts, Calendars, and Tasks which is what I’ve been wanting to sync with Outlook. The synchronization process began. I opened Outlook and all my data for Contacts, Calendars, and Tasks were synchronized with iCloud again. I did have to adjust my view in Outlook on a few things. I’ve been able to input new information and see it immediately on the iCloud.
For the record, my original post was Oct 27, 2015 11:29 AM. I’m running Windows 10 on a 5-year-old laptop (which was previously running Windows 7) and had upgraded my Outlook 2013 to Office 365.
I did not try any of the “work arounds” proposed in this thread. There was too much to wrap my arms around so I VERY painfully waited.
Meanwhile, I wonder…
Why did this error/problem happen? Could it have been prevented?
Why did it take Apple this long to resolve?
What changes will Apple make in the future to ensure this doesn’t happen again?
It’s hard to express how much trouble not having iCloud working with Outlook has caused me. I bought an iPhone because it synced with my Outlook. I had/have the expectation that I will receive prompt and continued support. Apple failed me in ways that has cost me lost productivity that I’ll never get back.
Although I’m relieved to have this fixed, Apple’s response to this matter will cause me to move forward with skepticism about Apple’s ingenuity, its commitment to customers, and their products.