Office 365 - Error 500, Could Not Connect, Invalid Credentials, Bad Username/ID/Password

This article applies to errors received trying to Test or run Discovery or Sync an Office 365 (O365) directory.

When configured for an O365 directory, the Source and Destination tab Test button might return Error 500.

When running a Discovery from or a Synchronization to an O365 directory, instead you may see an O365 authentication error:

Connecting to remote server outlook.office365.com failed with the
following error message : Access is denied. For more information,
see the about_Remote_Troubleshooting Help topic. 

Three possible causes of these errors from O365 are:

1. Unable to reach the Microsoft O365 domain

   • internet access down or can’t reach outside site

2. Typo in the O365 Login or Password on the Source and/or Destination tab of the connection

3. Permissions on install directory are insufficient.

4. IIS security be set up incorrectly

   • Disable Anonymous
   • Enable Windows Authentication

To Troubleshoot:

1. Try browsing directly to your o365 site and use the same authentication login/password
2. Update file permissions to apply Full Control for Everyone per this knowledge base article (step 1).
3. Check your IIS settings
4. Try using dirweb.exe to rule out IIS being the cause

If the troubleshooting steps above are not helpful, please contact our Technical Support team for additional assistance.