The error code 80044500 may occur when the Microsoft Dynamics CRM for Outlook Client Configuration Wizard fails to configure to the CRM organization. The user error may show:
“You're running an outdated version of Microsoft Dynamics CRM for Outlook that isn't compatible with your CRM organization”
This error when the user is running an outdated version of CRM for Outlook that is incompatible with the newer server version of Dynamics CRM.
Upgrade to a version of the Microsoft Dynamics CRM for Outlook client that is compatible with your CRM Server version.