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14 Episodes 2009 - 2009
Episode 1
On Tanabata, Mikuru takes Kyon three years into the past. There she is put to sleep by her future self, who tells Kyon to help out a certain someone. Kyon sees a young Haruhi sneaking into her school and helps her draw strange symbols.
Episode 2
Haruhi summons the SOS Brigade to make the most of summer vacation with a whirlwind tour of summer activities.
Episode 3
25 mins
With two weeks left of summer, Haruhi tries to plan the best for her and the rest of the SOS Brigade. Although the Brigade does everything from launching fireworks to catching cicadas to handing out balloons, Haruhi seems reluctant to admit that they did everything she wanted by August 30. Kyon spends the last night of summer struggling to finish the homework he put off during the whole summer.

Episode 4
25 mins
As the SOS Brigade tries to enjoy the last two weeks of summer to their fullest, Kyon gets an unwavering sense of deja vu towards the activities. After Mikuru becomes unable to time travel, they, Itsuki, and Yuki figure out that Haruhi as unwittingly trapped the Earth in a time loop. The last two weeks of summer have been repeating for over 500 years and will continue to do so until Haruhi finds a satisfactory conclusion. Only Yuki retains her memories of each scenario. On August 30, Kyon tries to talk to Haruhi in an attempt to end the loop, but fails to decide what to say.

Episode 5
25 mins
Once again, the SOS Brigade tries to enjoy the last two weeks of summer to their fullest. Once again, Kyon gets an unwavering sense of deja vu. Once again, Brigade members figure out the weeks have been repeating for over 500 years. Unfortunately, Kyon again fails to end the loop by August 31.

Episode 6
24 mins
As the SOS Brigade tries to enjoy the last two weeks of summer to their fullest, Kyon gets an unwavering sense of déja vu towards the activities. After Mikuru becomes unable to time travel, they, Itsuki, and Yuki figure out that Haruhi as unwittingly trapped the Earth in a time loop. The last two weeks of summer have been repeating for over 500 years and will continue to do so until Haruhi finds a satisfactory conclusion. According to Yuki, eight cycles have passed since the previous episode. On August 30, Kyon tries to talk to Haruhi in an attempt to end the loop, but fails to decide what to say.

Episode 7
24 mins
As the SOS Brigade tries to enjoy the last two weeks of summer to their fullest, Kyon gets an unwavering sense of deja vu towards the activities. After Mikuru becomes unable to time travel, they, Itsuki, and Yuki figure out that Haruhi as unwittingly trapped the Earth in a time loop. The last two weeks of summer have been repeating for over 500 years and will continue to do so until Haruhi finds a satisfactory conclusion. According to Yuki, three cycles have passed since the previous episode. On August 30, Kyon tries to talk to Haruhi in an attempt to end the loop, but fails to decide what to say.

Episode 8
24 mins
As the SOS Brigade tries to enjoy the last two weeks of summer to their fullest, Kyon gets an unwavering sense of deja vu towards the activities. After Mikuru becomes unable to time travel, they, Itsuki, and Yuki figure out that Haruhi as unwittingly trapped the Earth in a time loop. The last two weeks of summer have been repeating for over 500 years and will continue to do so until Haruhi finds a satisfactory conclusion. According to Yuki, three cycles have passed since the previous episode. On August 30, Kyon tries to talk to Haruhi in an attempt to end the loop, but fails to decide what to say.

Episode 9
24 mins
As the SOS Brigade tries to enjoy the last two weeks of summer to their fullest, Kyon gets an unwavering sense of deja vu towards the activities. After Mikuru becomes unable to time travel, they, Itsuki, and Yuki figure out that Haruhi has unwittingly trapped the Earth in a time loop. The last two weeks of summer have been repeating for over 500 years and will continue to do so until Haruhi finds a satisfactory conclusion. On August 30, Kyon tries to end the loop by inviting Haruhi and the rest of the Brigade to help him with his homework. Haruhi accepts, and after eight episodes spanning 15,532 cycles, time finally restores to normal on September 1.
Episode 10
24 mins
Anticipating the upcoming Cultural Festival, Haruhi holds a meeting to help decide how the SOS Brigade can participate. During the meeting, she announces plans to screen a homemade movie. Haruhi will write, direct, and produce, while Yuki contributes money from the Literature Club. The next day, Haruhi also hires Mikuru and Itsuki as the leads, Yuki as a supporting actor, and Kyon as assistant director. Kyon will handle all the parts of production Haruhi will not want to do. By the end of the day, the Brigade has acquired a camera for filming and guns for fight scenes.

Episode 11
24 mins
Fearing unknown dangers will arise during the production of the movie, Kyon promises himself to protect Mikuru. After school, Haruhi announces the roles she has assigned her actors. Mikuru will play a battle waitress from the future, Itsuki will play a young esper, and Yuki will play an evil alien. Over the course of the next few days, the SOS Brigade films commercials, Mikuru running, and a battle scene. Whenever Kyon asks Haruhi about the story, she simply assures him she planned out everything in her head and can change things later if necessary.

Episode 12
23 mins
During lunch, Haruhi informs the rest of the SOS Brigade that Mikuru must suffer as much as possible for the movie's ending to feel truly satisfying. Since it is forbidden to film at the shrine, they instead decide to re-shoot the fight scene. Haruhi orders Mikuru to shoot a beam from her left eye, causing Mikuru to unintentionally slice the reflector board and burn Yuki's hand. The rest of the day is spent filming random scenes of Mikuru's everyday life while she wears a bunny suit. The next day, Haruhi hires Taniguchi, Kunikida, and Tsuruya to play Yuki's minions.

Episode 13
23 mins
The SOS Brigade films Mikuru being assaulted at a private pond, then goes to Tsuruya's house to film Itsuki caring for Mikuru. When Haruhi drugs Mikuru into kissing Itsuki, Kyon engages in a fierce argument with Haruhi. Later, Itsuki informs Kyon that Haruhi is altering the world to suit her movie, as evidenced by Mikuru shooting beams and pigeons at the shrine turning white. Haruhi comes to school the next day in a depressed state. After talking with Itsuki and Taniguchi, Kyon reluctantly agrees to continue following Haruhi.
Episode 14
24 mins
As the SOS Brigade continues filming the movie, reality continues to lose order. Itsuki advises Kyon to make Haruhi aware that the movie is only fiction, or else she might bring disaster upon the world. To restore Haruhi's sense of reality, Kyon helps her come up with an ending for the movie, then has her record a disclaimer that the movie is a work of fiction. Although neither of them stay awake long enough to finish editing and visual effects, the movie is mysteriously completed just in time for the Cultural Festival. During the end credits of the episode, Kyon informs Haruhi that the other Brigade members are an alien, a time traveler, and an esper, but Haruhi responds by commanding Kyon not to trick her.
