My GF has the same problem, or rather, I have the same problem with my GF's outlook 2016. And when I try to do it manually, I come to a stop too. It asks to do it "automatically", but then it says something about the certificate being too old. My microsoft account is (obviously not exactly that) and I can't for the life of me figure out how to set it up again in Outlook 2016 after having removed as Microsoft tells me to. This month, apparently as the server for the calendar/email in Outlook 2016 is dead and gone, and I can't figure out how to "re-add" the account. I must be thoroughly stupid, but I feel like I have tried everything.
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