I've got it on side B in the program and on the printer. The issue is the eye not being able to find the black registration line. I make it to the process of manually positioning the line near the sensor. After it is set and ready to retry the registration, the printer feeds the substrate right past the eye. Needless to say, this is a bit frustrating as I am doing all I can to make it easy for the printer to do something it shouldn't have any issue with.
To anyone in the future having the same issue, I solved this problem by adding a 1" White Bleed to the front and back of my image. The contrast between the white bleed and the black registration line seems to make identification more accurate/easier.