Retrieving an old hotmail.com account password - how difficult is it?

User has lost his password and its linked to his itunes account
feck1Asked:
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slightwv (䄆 Netminder) Commented:
I tried to retrieve an old Hotmail account a few years ago but I didn't have any of my personal information linked to that account to verify I was who I said I was.  I wasn't successful and had to let it go.

If the user had personal information attached to the account, they might be able to verify their identity:
https://support.microsoft.com/en-us/help/12429/microsoft-account-sign-in-cant
RobertSystem AdminCommented:
I also went through the process and was successful as I happened to have entered information I was able to confirm my identity.
If you know the personal information you entered you can open a ticket and they will try to help but you basically need to be able to prove your the owner of that account which is difficult if you used made up information to remain anonymous.
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