OneDrive messaging not in sync with Skype, why?

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Windows Central Question

OneDrive messaging not in sync with Skype

(I apologize in advance for the length of this post; I want to make sure you experts have all of the background.)

My friend and I both have Live/MS accounts from way back, and we used to use MS Messenger to communicate.

After MS "upgraded" Messenger to Skype my friend started using the OneDrive web client for messaging. He also uses the iOS Skype app. I use only the Skype PC client.

We noticed this week that I was unable to send images or files to him. On my Skype client, the whirlygig kept spinning, and he never got any notifications on his end. I noticed that his entry in my Skype contacts list showed "Messenger: name@emailhost.com", and his profile did not have the normal Skype attributes. There was no "add phone number" for example and I could not see if he was online or not. Normal messages got through to him, though, both to his OneDrive client and his iOS app.

So I searched Skype directory for his name and it came back with several hits, some quite old. But the one with "Live: liveaccountid" in its profile - the same Live ID that he uses to sign into OneDrive and the iOS app - looked current so I added it to my contacts.

In my Skype client now, that profile shows up as a "normal" Skype account, and I can send images/files to it. BUT - my friend only gets the messages on the iOS app. His OneDrive client doesn't get anything.

It seems to me that the problem is in OneDrive somewhere. Somehow it is stuck in Messenger mode, and can't see anything sent to his Skype account. So to sum up:

In my Skype client, I have two entries for him: one says "Messenger: name@email.com" and the other says "Live: liveaccountid". First one works for messages only, to both iOS and OneDrive. Second one works for messages, images, and files, but only to the iOS Skype client.

In his OneDrive client, he has two entries for me: one shows as "X Y" (a very old display name I used to use back in the Messenger days) and one shows as "Xavier (Young)" (my current Skype display name). He can send (via Messenger API) to the old "X Y" display name, but cannot send anything from OneDrive to the new/correct "Xavier" display name. iOS Skype app works fine for sending to either.

I will be eternally grateful to anyone who can give us a clue WTH is going on. Seriously, some time between now and the heat death of the universe my ghost or spirit or whatever will say, "wow, I'm really glad that guy helped me with OneDrive in 2015."
 

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