Meaning you just put it on the trk & pumped it up with oil Travis?
Remove cylinder from trk, but do not remove oil supply hose to cylinder. Turn cyl upside down, hold it between both hands applying some resistance while extending cyl with running pump. Fully extended, stop pump, count to ten so air bubbles rise to the top (bottom of cyl). Then retract cyl using pump, keeping cyl upside down & maintaining force on cyl between your hands till it's fully retracted. Repeat 2 more times. It should then be completely air bubble free.
Works good if one person handles the cyl while a 2nd person operates the radio... me usually being by myself used my knee & one hand to apply force to the cyl while operating radio with other hand... kind of a juggling act that if it slipped off my knee, then I had to start over again.
I did this to my flagship KH back in 2000 & it continues to this day to go up & down without hesitation, loaded or empty box. Wedico telescope cylinder.