Outlook sync errors with Office 365 Software & Applications

From sync errors to sign-in challenges and collaboration setbacks, these common Office 365 troubleshooting techniques can restore service quickly.



Troubleshoot Office 365 Sync and Login Issues

We tackle these by making sure the reset went through, checking Azure AD Connect, and confirming each device uses the right sign-in setup. We keep password synchronization reliable by staying proactive and making sure users know how their actions affect access across Microsoft 365 and their devices. Even when sync works, cached passwords on devices can cause login failures. Windows, Outlook, and mobile apps often save passwords so users don’t have to keep typing them. If a password changes, those caches might still use the old one until you clear them out. The M365 sync establishes a synced dataset based on your M365 data and the filtering configuration of your sync.

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Outdated credentials get stuck on devices, password sync gets turned off, or Microsoft Entra Connect just doesn’t update like it should. Here’s a step-by-step approach to help you spot the issue, fix it, and avoid these sync delays down the road. While M365 is highly stable, it’s not immune to occasional disruptions. We also check the synchronization scheduler to confirm delta and full sync cycles finish successfully.

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



Troubleshoot Office 365 Sync and Login Issues

On Windows, open Credential Manager, pick Windows Credentials, and remove anything related to Office 365 or Microsoft 365. On macOS or iOS, delete stored credentials from Keychain Access. To update from Azure AD Sync Outlook data file cannot be accessed to Microsoft Entra Connect, see the upgrade instructions.

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



Troubleshoot Office 365 Sync and Login Issues

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 Summary sheet on the spreadsheet attachment of your sync summary includes an Updated User Count and User Limit. These figures will give you an impression of how far over the limit the account is. Sync failure alerts do not always include a full summary or credential loop in Microsoft 365 attachment, you can run a test sync to obtain this data.

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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 Exchange Connectivity Diagnostic devices to Microsoft 365 services.

Common Causes of Office 365 Password Reset Sync Issues



  • We also scan Event Viewer logs under Applications and Services Logs → Directory Synchronization for Event IDs like 650–657 (for sync activity).
  • Running the Azure AD Connect Health tool gives you alerts for sync errors and interruptions.
  • We also check the synchronization scheduler to confirm delta and full sync cycles finish successfully.
  • Sync failure alerts do not always include a full summary or attachment, you can run a test sync to obtain this data.
  • For managed environments, we use Intune or Group Policy to force sign-in credential sync and clear old tokens.
  • The system requires that users have a first name, last name and a valid email address that conforms with your domain lock if enabled.
  • You can stop any accounts from being brought over by adding them to the sync deny list.
  • Users I create within the Office 365 portal are fine, so I assume it is something to do with Azure AD Connect.


First, we check that the password reset finished in Microsoft 365 or Microsoft Entra ID. The user should log in to the Office 365 web portal with the new password. If the old password still works, the reset probably hasn’t synced. To avoid this, double-check that password writeback is turned on and working. You can run a sync manually with PowerShell or the Azure AD Connect tool to make sure updates go through. Checking the sync logs helps confirm password changes are making it everywhere they should.

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