Constant Prompt for Credentials from Outlook (O365)

I am having an odd issue, some users are constantly receiving a request to enter there credentials for Outlook and Skype. We have a hybrid O365 environment and for the life of me I can not figure out why this keeps happening. The fix I have found is to remove all saved credentials and then have them re-enter but for some users this happens every few weeks and it is extremely frustrating. Anyone else see this of know how to fix it? O365 support hasn't been much help.
Christopher HippensteelNetwork/ Systems AdministratorAsked:
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Senior IT System EngineerSenior Systems EngineerCommented:
Hi Chris,

Can you please check your Azure AD connect or the Synchronization software for the Office 365 Identities.

Last time I got similar issue, it was the server requiring restart and fix some dirsynch object error.
Christopher HippensteelNetwork/ Systems AdministratorAuthor Commented:
I am not sure what I am checking in Azure AD Connect? Could you let me know what I should be looking for?
Robert RComputer Service TechnicianCommented:
sometimes it may help to go into the credential manager and remove what has been authorized there especially if you had a password change.
Christopher HippensteelNetwork/ Systems AdministratorAuthor Commented:
Restarting the server nightly seems to have resolved the issue for now.

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