How do I add a directory, or bulk, of users to Microsoft SQL Server permissions
SOLUTION UPDATE:

To finish the set up you must type the name of the directory into the check names box and click check names to confirm it. This seems intuitive but it is an easy step to miss. Please reference the pictures below, also my folder was named users, yours may be something else:

The first picture is before clicking the check names button


This picture is after clicking the check names button