First half especially, Leeds had 2 or 3 players on him every time he had the ball, leaving him with nowhere to go but back into defence. When we make him hug the touchline, a persistent multi-player press can cut off all the progressive angles.
I'd assume the best way to deal with this would be for him to pass to the defence and the defence to bring the ball forward with speed and accuracy into the spaces vacated by those Leeds players being tight to Jack.
Unfortunately, Ake and Akanji, despite their other qualities, aren't really the players for incisive line-breaking passes, and Stones was very wide on the right, making passes from the left wing to him risky due to the press a lot of the time.
So Jack passes back to the defence, they pass it between themselves and by the time they start moving forward, Leeds are back in shape and we've lost our overload.
When we allow Jack in off the wing a little more, he has more options and is more effective, but that's not without its risk to our shape.