Cab and Nacho, on a ONE MAN bleeder, if you hit the end of the stroke and an air bubble is:

halfway between the caliper and oil catch can

and the catch can is BELOW the bleed,

that air bubble rises and goes back into the system.

If the catch can is ABOVE the bleed screw, then the air bubble travels UP to the catch can where it belongs and fluid drains down to the bleed screw.

This is Grade 2 Science, air rises in fluid.

Get a Helper next time and watch it, and you'll see what I mean. It's way faster and you use way less fluid my way.