"Shikadai's Doubts" (シカダイの迷い, Shikadai no Mayoi) is episode 44 of the Boruto: Naruto Next Generations anime.
As usual search procedures yielded no results, Kōtarō drafts the recently graduated genin into the search for the Byakuya Gang, instructing them to report anything unusual as they go about their regular missions, and not to engage them in battle. The genin discuss what to do if they are attacked, and Iwabee is surprised by Boruto's reluctance to battle. The Byakuya Gang commits a robbery near where Team 5 is aiding a construction company. Iwabee pursues them as they flee, and blocks their escape with earth walls. However, they easily break free, and Metal is injured while protecting Denki from an icicle. At the hospital, Udon lectures Iwabee and tells him to stay home. They watch news reports on the Byakuya Gang, and see they are well-received by poorer populations. At home, Himawari asks Hinata about the gang, and while Boruto agrees with helping those in need, he disagrees with hurting others to do so, and considers Naruto responsible, seeing the social inequities at question to be due to his ineffectiveness. Later, the genin discuss the gang, their merits, and methods. The Byakuya Gang prepares the robbery of a pawn shop. Ryōgi decides to go ahead, claiming to want to memorise the area. The others are concerned that Ryōgi could betray them, but Gekkō doesn't share their opinion. Boruto goes to Katasuke for more games. Spotting Shikadai in the park, Temari tells that she will be busy because every chūnin and above is going on missions because of the Byakuya Gang. Shikadai and Ryōgi play shōgi. They discuss the village and the recent attacks until Boruto arrives and shows Shikadai the limited edition games he got from Katasuke. Shikadai introduces Boruto and Ryōgi to one another. Boruto finds Ryōgi to be familiar. A cold wind blows when Ryōgi leaves. At the pawn shop, Ryōgi arrives late, and warns them not to flee towards the park, to avoid coming across genin. Sumire and Wasabi notice them robbing the pawn shop, but as they leave, the gang spots them and attacks. Temari attacks the gang, Namida arriving with her. Three of them escape, while Temari chases the other to the park, passing by Boruto and Shikadai. Temari asks them for diversions, but he manages to escape. Temari, having picked up on Shikadai's hesitation, tells him that it's ok to take risks sometimes, otherwise all the great things will pass him by. Ryōgi regroups with the rest of the gang, and Gekkō receives word of support from other villages, and decides to go ahead with the next phase of his plan.