It is my best guess (that could be a mistake) that a certificate needed to pass the Trust test in MS has not been updated or created by Apple since the introduction of Office 365 - 2106 (Outlook).
- I have mentioned this to the Sr Adviser who is bird dogging this with the engineering team responsible for iCloud and iCloud for Windows. At last one of two people have need the same complaint that on their MACs that sync will not work and the add-in is missing in Outlook for MAC too. I have tried changing the filtering for the Trust Center to see if the add-in would show up that the hate wide open. No such luck. I don't think a certificate is out there for 2016.
- Note somewhere in all this we also saw notations that 'click to run' versions of Office 365-2016 was not compatible with iCloud for Windows (iCloud for mail, calendar and contacts). Apple noted that those with Office 365 - Outlook 2016 should use their iCloud mail, calendar and contacts. This sure tells me that Apple's support / engineering for iCloud for Windows knew that their iCloud for Windows (4 and 5) would not sync with the new Outlook.
So, we cannot let Apple off the hook for responsibility to make their product work for us. If Apple needs something from MS to do their trick for iCloud for Windows, it has been long pass time that ask and get this done. MS knows this is not working too and points us back to Apple support. If you go to MS support and look around there are a few questions raised on this problem to the MS support.
I think by Monday, it will be time to ask for help on this from the top down rather than the bottom up. Let's see what the next 2 days bring then those who are willing may help in a letter writing campaign to Tim Cook.I hope this post survives the monitor who seems to not be able to move problem up the chain but can erase whatever discussion is deemed 'inappropriate'.
BWWIGGS