According Richard's marker on the maps, Richard and Lilly just keep going up and down the same road after he is captured.
When the Confessor is releasing the Seeker from the back of the cart, the two bounty hunters surprise them. The bounty hunter holding the bow has the arrow on the wrong side of the bow. It should be on the same side as the hand holding the bow to prevent the very problem he had, needing to hold the arrow with one of the fingers. The very next scene, he makes another mistake by swapping hands. The left hand is now holding the string while the right hand is holding the bow, and the arrow is again on the wrong side. Further, given the placement of the quiver over the right shoulder, the person was a right hand draw, meaning in holding the bow with his right hand, he would not have been easily able to get a replacement shaft. Given he was a bounty hunter and using the bow as a weapon, he would have known how to use it, and so should not have made such fundamental mistakes with the basic usage.