I have the same problem with a Lenovo laptop running Windows 10 and Office 2016. The iCloud Outlook Add-in shows Active in Outlook.
I found that iCloud hangs saying “Setting Up” the first time after installation. If you cancel it and start again, re-tick the box and Apply, it either comes back with a blank box, or it comes back with a ticked box which is actually a lie: if you close iCloud and re-open it, the box is unticked.
If you look at the Event Viewer (Windows key, type Event Viewer), it shows an error at the time you clicked Apply. Expand Windows Logs in the left-hand pane of the Event Viewer, and click on Application. Error is shown below, but I’m none-the-wiser. I have raised this on Microsoft’s Support forum, and will post here if anyone suggests a resolution. For reference, the thread is here:
https://answers.microsoft.com/en-us/office/forum/office_2016-outlook/communicati ng-between-outlook-and-icloud-icloud/f8d7802d-a51c-4af9-bb6a-c8f6556049cd?tm=146 6442835668.
Might be worth noting that I have this working correctly on another Dell laptop also running Windows 10 and Outlook 2016, with a different Apple ID for iCloud. Can’t spot the difference, and the working Apple ID doesn’t work on this Lenovo laptop, so perhaps it’s a PC configuration issue.
The error reported in Event Viewer is:
Log Name: Application
Source: Application Error
Date: 19/06/2016 16:38:20
Event ID: 1000
Task Category: (100)
Level: Error
Keywords: Classic
User: N/A
Computer: Lenovo
Description:
Faulting application name: AppleOutlookDAVConfig.exe, version: 4.8.24.0, time stamp: 0x56cc1f98
Faulting module name: mso20win32client.dll, version: 0.0.0.0, time stamp: 0x57459f65
Exception code: 0xc0000005
Fault offset: 0x000ae519
Faulting process id: 0x2c14
Faulting application start time: 0x01d1ca409177bdee
Faulting application path: C:\Program Files (x86)\Common Files\Apple\Internet Services\AppleOutlookDAVConfig.exe
Faulting module path: C:\Program Files (x86)\Common Files\Microsoft Shared\Office16\mso20win32client.dll
Report Id: 87fa0c2a-da60-4ea7-a16d-ea649d326168
Faulting package full name:
Faulting package-relative application ID:
Event Xml:
<Event xmlns="http://schemas.microsoft.com/win/2004/08/events/event">
<System>
<Provider Name="Application Error" />
<EventID Qualifiers="0">1000</EventID>
<Level>2</Level>
<Task>100</Task>
<Keywords>0x80000000000000</Keywords>
<TimeCreated SystemTime="2016-06-19T15:38:20.078485900Z" />
<EventRecordID>32507</EventRecordID>
<Channel>Application</Channel>
<Computer>Lenovo</Computer>
<Security />
</System>
<EventData>
<Data>AppleOutlookDAVConfig.exe</Data>
<Data>4.8.24.0</Data>
<Data>56cc1f98</Data>
<Data>mso20win32client.dll</Data>
<Data>0.0.0.0</Data>
<Data>57459f65</Data>
<Data>c0000005</Data>
<Data>000ae519</Data>
<Data>2c14</Data>
<Data>01d1ca409177bdee</Data>
<Data>C:\Program Files (x86)\Common Files\Apple\Internet Services\AppleOutlookDAVConfig.exe</Data>
<Data>C:\Program Files (x86)\Common Files\Microsoft Shared\Office16\mso20win32client.dll</Data>
<Data>87fa0c2a-da60-4ea7-a16d-ea649d326168</Data>
<Data>
</Data>
<Data>
</Data>
</EventData>
</Event>