In case anyone else runs into this, I did figure out my issue. I had to change my filter back so that pass was being picked up as User_Password. I also hadn't been positive about the Password Type field, if that was for the users in the database or for my initial connection to the database. It is for the users in the database.
The other part that really confused me was the tcp/ip connection timeout errors I kept getting after trying to save my filter when my filter looked correct. After sniffing packets I finally figured out that although I had a port in the Port (Optional): field; the filter tab (which I was essentially using as a diagnostic tool) completely ignores the port field, at least for the MSSQL driver. The authentication was using the correct port, but that filter tab was using the default so it kept throwing out errors. I'm running CPPM 6.5.5.78974. I setup a new database instance with default ports to not cause confusion going forward.