After working fine for years, suddenly iPhone and Outlook stopped syncing contacts and calendars. Outlook started throwing off messages a la, “Outlook had a serious problem with the iCloud Add-In, do you want to disable it?,” and the iCloud tab and Refresh button disappeared from Outlook. None of what I’ll politely call the ‘easy fixes based on standard instructions’ you so often see about things like this all over the Web did a thing to change the situation. Here’s how I solved it:
 In Outlook 2010: File > Options > Add-ins. That brought me here:
This is actually the ‘after’ view–after I fixed this. The view when I attacked this problem was identical except that iCloud Outlook Addin was appearing under Disabled Application Add-ins. No, I am not disabling it and going through the process all over again for the sake of this piece. There is journalistic integrity–and there is “Why in God’s name did you touch it again after you rescued it the first time?!” But I digress…
Anyway, noticing the file location paths, I typed in a separate note the file location for the iCloud Add-in shown above: C: > Program Files (x86) > Common Files > Apple > Internet Services > APLZOD32.dll. You’ll see why in a minute.
The page is preset to Manage COM Add-ins, and I pressed [Go].
In this view I selected the Cloud Outlook Addin* to highlight it, as shown above, and pressed [Remove].
 Next, in this same view I next pressed [Add…], and navigated to the file location I had found above, which brought me here:
I selected the file, saw it was now listed in Active Application Add-ins, and noticed that, miracle of miracles, the [iCloud] tab at the top of the Outlook window, and the [Refresh] button, had returned. Yes, syncing iPhone to Outlook could actually be a refreshing experience again.
So far so good, but any dev and probably many readers know what comes next: TESTING.
I held my breath as I tested it: added and deleted Calendar and Contact items, and modified existing items, on iPhone and in Outlook, and they are now updating both ways—iPhone-to-Outlook and Outlook-to-iPhone—either immediately in front of my eyes, or when I hit Refresh.
“Victory is mine”…and, if you’ve been seeking a solution to this problem: YOURS. We’re all in this together.