How to Troubleshoot Common Microsoft 365 Problems and Issues

Even I've only been doing this with test users so far, so haven't actually broken any actual users yet, I still need to get this resolved quickly.



Troubleshoot Office 365 Sync and Login Issues

For managed environments, we use Intune or Group Policy to force sign-in credential sync and clear old tokens. Boost your SMB’s security and compliance with Microsoft 365 Business Premium. Discover Defender and Purview add-ons for enterprise-grade protection at SMB-friendly pricing. This means that the authentication setup for your sync is no longer valid. This can happen for the a number reasons particularly if your sync authenticates using Delegated Permissions. You will need to have the correct privileges set on your Azure account in order to set up the M365 sync.

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What to do when Office 365 password reset doesn’t sync across devices



Troubleshoot Office 365 Sync and Login Issues

I have multiple users experiencing sync errors with Outlook and office365. Another which is shown below, is a user opens a new message, or replies to one, and lets it sit for a while. When they go back to the message and press send they get an error that the message has been deleted. Ive repaired the OST and changed cache mode to only cache 1 year. With directory synchronization, you can continue clear Outlook credentials manager to manage users and groups on-premises and synchronize additions, deletions, and changes to the cloud.

Login & Sync Errors: Personal & Business Microsoft 365 Accounts on Same Device





Bad settings in Azure AD Connect cause lots of password sync failures. If password writeback isn’t enabled or the service account doesn’t have the right permissions, new passwords won’t update in Active Directory. That leaves people locked out with their new password on the cloud but not locally. We show users how to reset passwords using approved methods like the Microsoft 365 portal or self-service password reset (SSPR). If someone changes their password only in the cloud or just on a local system, things can get out of sync pretty quickly.

Reviewing Device Sign-In Settings



Troubleshoot Office 365 Sync and Login Issues

The Users Processed count will be 0 is there are no users in the synced dataset after filtering. The sync will fail if the groups you selected to load users from no longer exist in Azure AD. Typically this is because the selected groups have been deleted from Azure AD since the M365 sync was configured on your account. To get the sync working you will either need to delete users or have the user limit on your Exchange connectivity diagnostic account increased. Users I create within the Office 365 portal are fine, so I assume it is something to do with Azure AD Connect. We have reset the router, checked internet speeds, signed in and out of M365 apps, reinstalled apps and checked for Windows updates.



Password sync usually fails when credentials don’t update between Microsoft Entra ID (Azure AD) and your on-premises Active Directory. Most of the time, the problem comes from timing delays, configuration mistakes, or cached credentials on devices that don’t pick up new passwords. We check that Microsoft Entra Connect (Azure AD Connect) runs the latest version and password sync is on. Keeping things updated helps avoid compatibility issues between on-premises Active Directory and Microsoft 365. If problems stick around, we rejoin the fixtechguide Windows update outlook fix devices to Microsoft 365 services.

Common Causes of Office 365 Password Reset Sync Issues



  • The sync does not delete users but rather sets them to inactive.
  • The M365 sync establishes a synced dataset based on your M365 data and the filtering configuration of your sync.
  • On macOS or iOS, delete stored credentials from Keychain Access.
  • You will need to have the correct privileges set on your Azure account in order to set up the M365 sync.
  • Checking the sync logs helps confirm password changes are making it everywhere they should.
  • Bad settings in Azure AD Connect cause lots of password sync failures.


You should run a test sync after re-authenticating the sync to ensure it is working. Devices sometimes keep using cached passwords even after a successful sync. If users access multiple apps with the same login, we make sure Single Sign-On (SSO) settings line up so the new password works everywhere in Microsoft 365. If there’s a delay, we manually trigger a password sync using Microsoft Entra Connect.

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