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"The place Kiriko sought to be her final abode was prison..." ― A hilarious yet poignant account of a lonesome woman's quest for comfort in her old age ― Kiriko was in deep despair. Amidst her barely manageable life relying on her meager pension and part-time income, her best friend and sole source of consolation had just died, and she was suddenly facing days of emptiness. Then one day she sees on TV a man arrested for theft claiming that he had nothing left to hope for in his life, and that he had committed his crime for the purpose of going to prison. Inspired by this thought, she sets prison as her final home, and begins to search for ways to get arrested with the least amount of trouble caused to other people.

Kiriko, in her "prison challenge," sets her sights on robbery. She infiltrates the office of black-market money lender Terada Kazuo by offering to work there as a cleaner, thinking that stealing the big amount of cash stashed there and getting arrested would send her to prison. She searches the safe and other likely hiding places for the money, but during her unsuccessful attempts she ends up inadvertently capturing another thief who had come to raid the office, and getting thanked by Kazuo. Will she ultimately consummate her planned theft?

Kiriko hones in on marriage fraud as her next crime. She attends a seminar for women on the fraudulent art of drawing money from men, and learns that the seminar is run by Koike Yukari, who had conned money out of Kiriko's acquaintance Mikasa Takashi. Kiriko goes to try her luck at match-finding events for senior-aged men and women, and though her long hiatus from dating inhibits her, she unexpectedly forms rapport with a seemingly ideal man. But as she heads to her first date with him, she deliberates between prison life and married life.

Kiriko is told to move out of her apartment, and in desperation she decides to pursue kidnapping. By this time a group of characters have formed to assist her prison challenge, including her work boss Kudo Itsuki, the money lender Kazuo, and Enomoto Yukina, a young girl she had befriended. They put together a scheme of kidnapping Yukina and getting a ransom for her. Kiriko somehow makes it through the kidnapping, the phone call demanding ransom and the receiving of the ransom, but when she finally thinks she would successfully be arrested, the matter takes an unexpected turn.

Having seen Kiriko's crime attempts take wild turns and end in failure, money lender Kazuo suggests to her the ultimate crime: murder. Knowing that he is stricken with cancer, he asks Kiriko to murder him, so that he could "die like a bad man should." Kiriko refuses this offer at first, saying that murder is outside her conscience, but then she considers Kazuo's sentiments and the days spent with her associates, and she wavers. What will she decide, and what world will she see beyond her ultimate crime attempt?