I agree with @salamander uchiha+ for the most part but for Naruto it's a special case. Since Jiraiya uses
So you can make an argument that he surpassed him when he learned Kyubi chakra mode for the first time but if you want to be 100% literal then you would have to say War arc Sm Naruto surpassed Jiraiya.
Hebi Sasuke surpassed armless Orochimaru but with arms I would say MS Sasuke or possible EMS if you count his EdoTensei. Sakura reached Tsunade with 100 healings, I do not believe she surpassed Tsunade because only Tsunade's 100 healings can have her body completely severed then re-attached back again using Katsuyu. Sakura would instantly die if her body was severed completely like Tsunade's did during the edo Madara fight.
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, that means Pain arc Naruto is only stronger for the first few minutes of their fight.So you can make an argument that he surpassed him when he learned Kyubi chakra mode for the first time but if you want to be 100% literal then you would have to say War arc Sm Naruto surpassed Jiraiya.
Hebi Sasuke surpassed armless Orochimaru but with arms I would say MS Sasuke or possible EMS if you count his EdoTensei. Sakura reached Tsunade with 100 healings, I do not believe she surpassed Tsunade because only Tsunade's 100 healings can have her body completely severed then re-attached back again using Katsuyu. Sakura would instantly die if her body was severed completely like Tsunade's did during the edo Madara fight.