While Uryū Ishida and Orihime Inoue were watching Kenpachi Zaraki and hiding on top of a building in the court of pure souls, he found Orihime distracted and almost killed her. However Uryū notices this and saves her. After conversing for a short while, with Jirōbō doing most of the talking of how little chance they stood against him along with the regret they should be feeling, Uryū interrupted him by destroying his Zanpakutō's release, bringing him to his knees. Jirōbō uses his uninjured arm in an attempt to attack Orihime afterwards, either to take advantage of her vulnerability or take her hostage, but Uryū fires arrows through his soul chain and soul sleep. This causes him to lose his Shinigami powers and as a result of losing his power, he presumably loses his position as a Shinigami.
Jirōbō is a very boastful man, talking the entire time during his fight with Ishida simply about how they should give up since he is the greatest projectile expert and so on. He is also very cowardly. Jirōbō attempted to kill Orihime while she did not notice, and upon realizing the difference of power between Ishida and himself, attempted once again to either injure or capture her. This placed him at odds with the chivalrous Quincy, resulting in the loss of his abilities.