Your two most pressing Outlook iCloud Sync issues SOLVED

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If you are reading this, you probably want to be able to add or change contacts or calendar items in Outlook on your computer and have them reflected, ‘through the magic of iCloud,’ on your iPhone, and vice versa, from phone to computer. That was all I wanted, but I hit some walls that seemed insurmountable until I found solutions posted by some expert and helpful users. I decided to post them together to offer you, the reader, one-stop shopping to these fantastic fixes.

ISSUE: “Setup cannot continue because Outlook is not configured to have a default profile.”
This one smacks you in the face right out of the gate, after you have installed iCloud and are in setup. You check the box to tell iCloud to sync Mail. Contacts, Calendars, and Tasks, hit apply–and you get the message above. After rapidly descending on an estimated 11 zillion sites with solutions that did not work, I found one that did.
SOLUTION: Close iCloud. Open File Explorer, go to c: \ Program files(x86) \ Common files \ Apple \ Internet and find the file simply called iCloud (it’s icloud.exe, but the extension may not be visible). Right-click it and choose Properties. Click the Compatibility tab and you should see something like this:

The compability troubleshooter button is highlighted, and I pressed that and put the system through its paces, but ultimately all you have to do is check the box and select the pulldown menu so it reads as it does here: “Run the program in compatibility mode for Windows 8.” Press [OK] at the bottom.

Now open iCloud again, check the box for Mail. Contacts, Calendars, and Tasks, hit apply, and it should go through its sequence to set up iCloud and Outlook to sync.

ISSUE: Contacts are syncing but calendar items are not.
I again found a number of sites with well-meaning solutions that weren’t, but thankfully found one pretty quickly that worked.
SOLUTION: Open Outlook, choose calendar, and double-click in a date box to set up a new Appointment. You’ll notice Calendar at top left.

Your calendar may be defaulting to Outlook Data File as mine did:

If so, use the slider to page down, find your iCloud calendar, and check the box for Calendar:

I was going to say this is not a permanent solution because you will have to do this every time. However, it appears that if I just remember to keep the iCloud calendar checked instead of letting Outlook select Outlook Data File as the default calendar to show, new calendar invites I create are coming up correctly in iCloud calendar.

To close the loop, I double-checked whether calendar entries I create in iCloud are syncing to Outlook. iOS lets you preset the calendar in which new Appointments are created. So yes, new Appointments I create on my phone are syncing fine in Outlook without any adjustment.

As some of my friends in other parts of the world like to say: “There you are. All sorted.”

I am guilty of having saved content and screenshots in my files, but not links to the pages where I found this sage advice, to give credit where due. Thank you, solution providers. You know who you are, and you have my eternal gratitude.

 

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How iPhone Got Her Outlook Back

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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:

[1] 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].

[2] That brought me here:

In this view I selected the Cloud Outlook Addin* to highlight it, as shown above, and pressed [Remove].

[3] 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.

*Whoever was in charge of placing dashes in filenames missed on the iCloud and VBA (Microsoft Visual Basic for Applications) “addins,” or as they’re widely known: Add-ins.