Unable to login to Windows 10 with Microsoft account constantly receiving PC Offline message

Andrew N. Kowtalo
Andrew N. Kowtalo used Ask the Experts™
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I have a windows 10 machine that is currently giving me the message Your PC is offline.  Please sign in with the last password used on this PC.

The Microsoft account that was used with the device has not been used in ages.   I was able to reset the password for it from the Microsoft portal and verified I could log into it and was able to access the inbox.  Its an outlook.com account.

I then connected to the laptop to the local network and gave it internet connectivity out, however when I try to sign in with the new password I updated the machine still gives me the message that the PC is offline with the associated account.   I have no way to switch user or login using a different account as this laptop was only setup with the outlook.com account.  

I know the machine has been off for quite sometime, do I just have to let the laptop sit and stay connected to the network and will it eventually go online by itself allowing me to login to the Microsoft account or is there a work around?  I was told I can not format this laptop as there is data on it that is needed so if someone could tell me how I can login to the machine with this outlook.com account it would be appreciated.

This is the CEO's machine so this is pretty mission critical.

Also I have had this laptop connected wirelessly and wired with internet connectivity and have let this sit now for about 30 minutes.  

She has critical files on here she needs so reformatting is out of the question.

How is it possible that the machine reports offline even though it is physically connected to the network and getting out to the internet!?
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Andrew N. KowtaloSupport Center Engineer

Author

Commented:
So it looks like Windows is asking for the last cached password that was entered correctly on the machine.   Unfortunately the user does not know the last successful locally cached password she logged in with.   They gave me 5 different passwords none work.
Top Expert 2013
Commented:
you can take out the disk drive, and copy the documents you need over - to gain time for the repair of the MS account
Andrew N. KowtaloSupport Center Engineer

Author

Commented:
As much as I didn't want to take that route it may be possible.  I know This user has her taxes on her laptop however I do not know where they are located.  

I did manage to login to her O365 account and there was only 2 emails in it, which means all of her email is probably stored in her outlook.   I am assuming she never exported her email so I highly doubt there is a PST file.  Part of me wonders if there is an application that can over ride that login as I really need to get into the account.   She even showed me the password that was associated with the account on her phone and passwords, I tried that left right up and down backwards and forward and it kept telling me offline.  So there is a cached password in there, I just don't think I will be able to get in.
Top Expert 2013

Commented:
are you sure it is connected to the internet?
in case case -  here the normal procedure :  https://www.nextofwindows.com/how-to-deal-with-your-pc-is-offline-message-in-windows-8

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