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Early in the second test of the Chuunin Exam, Oboro poses as Naruto to surprise Sasuke and Sakura. Sasuke sees through the transformation quickly as Oboro failed to copy Naruto exactly. Revealed, Sasuke and Oboro fight. Using his Sharingan Sasuke manages to get the upper hand and injure Oboro. Bleeding, Oboro retreats to attack again later.

Later in the second test, Oboro and his teammates use an illusion technique to cause Naruto, Sasuke, Sakura and Kabuto to walk around in circles and waste their time. When the group discovers the deception, the Rain Genin begin to attack the group with bunshin clones. From a hidden view point above, the Rain Genin are able to control the clones and launch kunai at the group below. Naruto decides that if all the clones are attacked at one time, the location of the Rain Genin will be revealed. Naruto then uses his Kage Bunshin and proceeds to fight the clones all through the night. By the next morning Naruto and the group are exhausted so the Rain Genin decide to reveal themselves and strike. Naruto held one more trick up his sleeve, the version of Sakura, Sasuke and Kabuto that were along with him here Kage Bunshin clones of his using the transformation technique. Standing behind the Rain Genin, the real Sasuke, Sakura and Kabuto then reveal themselves. Not expecting that revelation, the Rain Genin are momentarily unsure what to do. Sasuke tells Naruto that he can rest now, but Naruto does not want to show weakness in front of Sasuke. Striking quickly, Naruto punches all three of the Rain Genin.

Taking one last stand, Oboro uses a mist clone technique to create multiple clones of his Genin team. Naruto states that one must be the real version so he begins to attack the clones. Passing through them Naruto is unable to find any real physical bodies. Sasuke uses his Sharingan to see that none of the clones in front of them are real. Seeing Kabuto and Naruto off guard, the real Rain Genin rise from the ground and attack Kabuto. Kabuto is injured and they are surprised when they see Kabuto show a great deal of power behind his anger at being hurt. Using the opening Naruto then kicks all three of the Rain Genin and knocks them unconscious. Having their scroll taken by Naruto's team, Oboro and his teammates do not pass the second test of the Chuunin Exam.

After the Chuunin exam the Rain team resumed Genin work. With the Jounin Aoi, they accepted a mission to aide the Wagarashi family in winning the Todoroki shrine race held in the Tea Country. During this period, the whole team furthered their skills and learned the Mizu Bunshin ability. Oboro himself improved his Genjutsu. While Oboro went to stall Idate, Kagari and Mubi prepped a ship for naval combat. After sinking Idate's ship, the Rain Genin went to battle Team 7 underwater, where they held the advantage. However, Naruto used his Rasengen training to hand them another humiliating defeat.

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After Akatsuki seemingly kidnapped the Raikage’s brother Killer Bee, the Raikage ordered Samui and her team to head to Konoha to gather information on Uchiha Sasuke. Little did the group know that Killer Bee had actually avoided capture, and used the opportunity to leave his village. When the Raikage gave his impassioned speech that they had to save his brother, both Omoi and Karui were moved to tears as well.

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The elder toad foresaw the coming of a young boy to Myouboku Mountain. This boy was Jiraiya and the toads taught him their jutsu. Some years later the toad asked Jiraiya to again come before him. He foresaw that Jiraiya would one day become a great pervert and travel the world. He also saw that Jiraiya would train an apprentice, one who would either bring destruction or peace to the world. The toad believed that Jiraiya alone would decide which fate befell the world. It is unclear whether the toad himself is still alive, leadership of the toads apparently changed to Gamabunta some time after.

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The young man known as Orochimaru was selected to study as a Genin under Sandaime Hokage. A quiet and focused young man, he impressed his teacher and grew more and more skilled as the years passed.

Over time Orochimaru became obsessed with learning every possible jutsu and extending his own life. Sandaime Hokage had hoped Orochimaru would become the next Hokage but Orochimaru began to grow reclusive and cynical with life in the village. Sandaime thus chose another man to follow in his footsteps. Around this time Orochimaru began his murderous experiments. He dedicated himself to bizarre experimentation. When Sandaime Hokage found out, Orochimaru fled. Jiraiya had a hard time believing the revelation and he took off after his friend, determined to get him to return. They battled and Orochimaru prevailed.

Soon after he joined the mysterious Akatsuki, a group of missing-nins whose goal was to travel the world gathering jutsu and eventually gain possession of the bijuu. Orochimaru would eventually leave the group after several years. It was during this period when Uchiha Itachi joined. It is not entirely clear if Orochimaru left Organization purely because of his feelings toward Itachi or some other disagreement with the group. Though he left, he would carry one memento from his time with them. A jar in his compound would hold his original body's hand with his Akatsuki identification ring.

His hatred of Sandaime Hokage and his village would continue in the years to come. It would help drive him to invade Leaf and cause its destruction. Orochimaru would return to Leaf during the Chuunin Exam to determine if Uchiha Sasuke would be a worthy vessel to hold his spirit. Orochimaru had perfected the body switch and wanted a powerful body with the Sharingan ability to help him learn all the jutsu of the world.

Though he faced his former sensei in battle, he never did get the upper hand. Orochimaru was forced to retreat after the Third Hokage removed his ability to use jutsu techniques. He fled Konoha once again and returned to his compound battered and angrier than ever before. Orochimaru recognized his options were limited, so he sought out his fellow teammate and Sannin Tsunade.

A skilled medical ninja, Tsunade carefully weighed Orochimaru's offer to heal him in exchange for the resurrection of his dead brother and boyfriend. She eventually rebuffed his manipulation and he again retreated to his secluded hideout. With his body nearing its end Orochimaru was forced to play his final card and switch bodies. He would no longer be able to take over Uchiha Sasuke until his three year session in his new host body played itself out. While he began to adjust to the new body, he waited patiently for the arrival of Uchiha Sasuke. When Sasuke finally arrived at Orochimaru's compound, Orochimaru began to teach the young man many of the jutsu his knew. All with the purpose of dragging out the months to make the body primed for his arrival.

After several years Orochimaru and his confidant Kabuto decided it was time to settle an old score with Akatsuki. Kabuto had been placed with Orochimaru as a spy by Sasori, Orochimaru's old Akatsuki partner. Orochimaru knew this early on and removed Sasori's jutsu on Kabuto. When Sasori arranged to meet Kabuto once again, Orochimaru and Kabuto planned to take him out. They were surprised by Team Kakashi instead. Orochimaru would once again face Naruto and be forced to change his plans once again...