Over the years, I ended up with several Microsoft accounts, and it is a mess. Here is how it happened.
I had a Microsoft account since time immemorial, associated with my personal e-mail. I had my MSDN subscription under this account.
I also had a Hotmail account since time immemorial.
I had a Skype account since time immemorial, too, associated with my personal e-mail. I used my standard, preferred username as my Skype name.
The Hotmail account became an Outlook account once Microsoft acquired Hotmail and created outlook.com. Thus, this became a separate Microsoft account. My standard, preferred username became a Microsoft Live ID.
So here is what I wanted to do at one point: I wanted to use my personal e-mail as my Office 365 and SharePoint online login. But for reasons I no longer remember, there were obstacles along the way. To resolve this problem, I first moved my MSDN subscription to my Outlook account. I then changed my old Microsoft account to be identified not by my personal e-mail but by my Gmail address. This freed up my personal e-mail address to be used as an Office 365/SharePoint online user account.
But then, one day when I was trying to use Windows 10 Quick Assist to offer assistance to someone, the software told me that I need not only to log on to Microsoft, but associate my account with my Skype account. OK, I’ll bite the bullet, I said… and associated my original Microsoft account (now under my Gmail address) with Skype.
And now I am having a problem. Skype tells me that my account has two aliases: The Gmail address and my standard username. But if anyone sends a contact request to my standard username, I get nothing. Today, I figured out why: these requests go to my other Microsoft account! (The one I never used with Skype.) Presumably it’s because my standard username also happens to be my Microsoft Live ID.
Curiously, if I actually log on to Skype using my standard username, I get connected to my Gmail-associated Microsoft account (which is what I want.)
Needless to say, there is no option to merge two Microsoft accounts. There is no option to unmerge a Microsoft account and a Skype account either. I cannot even add my old personal e-mail address as an alias to either of my Microsoft account; presumable because it is now set up as my Office 365/SharePoint online user account, I receive an error message indicating that a “work or school” e-mail cannot be an alias.
As far as I am concerned, this is an unholy mess. Just writing down what happened made my head spin a little. And I really wish I didn’t have to waste a good two hours of my life earlier this morning simply to get to the bottom of it all. (It all began when I made an unsuccessful Skype-to-landline call to Hungary and tried to call again using Skype on my mobile; the software, having updated itself, asked me to log in, and inadvertently, I logged in with the wrong ID. Bad idea, which I eventually remedied by shutting down Skype, deleting all Skype data on the phone, and then restarting Skype and starting all over again.)