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The worst is I cannot find any reason why it's still asking for password and in very random intervals. Their login to OWA works correctly so password is correct too. Few users using Outlook 365 started reporting that their Outlook keeps asking for password and when I was remotely connected to those users, they used correct username and password in the prompt (so there is not any problem with DOMAIN\ or username format). Office 365 does not have exchange online setup and there is not authorized domain, so there couldn't be any colision with on-premise exchange autodiscovery. I would like to ask if you didn't face the similar problem last few weeks when using Outlook 365 connecting to on-premise Exchange 2019.
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