Intermittent T.O. Bearing Disengagement with Wilwood High Volume MC

[BANKO]

Hey guys, I just swapped in a new MC from Wilwood (3/4" bore 260-6764) while my others are being rebuilt. I've bench bled the MC and also bled the T.O. bearing line. I noticed an issue today while driving that when holding the pedal to the floor for long periods of time, the clutch disengagement will become progressively closer to the floor. It resulted in me not being able to engage my T56 into gear. I tried pumping the pedal a few times, but it didn't seem to help. Then it just began functioning without issue. I checked the fluid level and it seemed slightly low, so I re-filled the MC. I suspect there may be air in the lines or the T.O. bearing is leaking.

Got any tips on how I can diagnose?

Thanks!