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SBS 2011 Essentials: "Your Office 365 password is not the same as your Windows password"

Posted on 2014-03-27
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Last Modified: 2014-04-08
I'm receiving alerts from an SBS 2011 Essentials Server for some users: "Your Office 365 password is not the same as your Windows password".

I've checked the Office 365 tab on the SBS Dashboard, to ensure that it's "talking" to Office 365, and sure enough it's able to read the Organisation details, Subscription details etc.  I assume this means that the server has an up-to-date administrator account / password for Office 365.

So I'm puzzled as to why the password sync issue is occurring.  As far as I understand it, when a user changes their on-premise domain password, the server connects to the Office 365 service and changes the user's O365 password to match.

The users are correctly linked to their Office 365 accounts in the Users tab of the SBS dashboard.

So why should this be happening?  Might a user have changed their O365 password independently via the O365 portal or OWA?  What would happen if they did - would the server change it back to match their on-premise domain password again?

Finally (I'll avoid adding a fourth question to the preceding paragraph), the most important question: how can I make this work properly and stop generating alerts?
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Question by:wakatashi
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by:Vasil Michev (MVP)
ID: 39959770
Perhaps they changes the password in Office 365, or the new password didnt comply with the O365 policy. Check this article and the references within for more info:

http://support.microsoft.com/kb/2652040
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wakatashi earned 0 total points
ID: 39975604
Thanks Vasil.  I checked with the users, and it turns out that they changed their domain password on their PC rather than directly changing their Office 365 via the Web interface.

I got them to check that they could restart the PC and log on successfully with their new password (they could), and that they could access their mailbox at https://mail.office365.com using their new password also (they could).  So it looks as if despite the alerts I was getting from the server, the password syncing mechanism is working after all.

However, dialog boxes have been appearing several times per day for each user, prompting for credentials.  I got them all to rerun the Office 365 Desktop Setup, and this has solved the problem.  The users are no longer being prompted to reauthenticate, and the server's no longer sending alerts about out-of-sync passwords.
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by:wakatashi
ID: 39985527
More troubleshooting led to more information, with which I was able to solve this myself.
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