This Operating System Is Not Presently Configured To Run This Application

This is an issue with updated DLLs in Office 2016 conflicting with third-party software applications, including AbacusLaw by CARET. The solution is to delete the Abacus Outlook add-in DLLs, and update AbacusLaw by CARET.
Delete the Outlook add-in DLLs, located in SysWOW64:
- AbacusMO.dll
- AbacusOfficePlugin.dll
- AbacusRedemption.dll
Change to Install mode and run the AbacusLaw by CARET update as admin.
Once done and back in Execute mode, test by opening and closing both Outlook and AbacusLaw by CARET as the user at least three times.