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In 2018, the Ninth Circuit ruled in Martin v. City of Boise that the city’s ordinance criminalizing individuals for sleeping or camping outdoors in public space—an increasingly popular method for cities to regulate the homeless—is unconstitutional under the Eighth Amendment’s Cruel and Unusual Punishments Clause. Martin was not the first case in which a court struck down an anti-homeless ordinance under the Eighth Amendment. However, it was the first to deem it unconstitutional for a city to punish a homeless person for sleeping outside when shelters are not “practically available,” even if they technically have available beds. The court in Martin said the shelters at issue were not practically available because they were religiously coercive. This Note argues, however, that courts reviewing criminalization measures should consider whether shelters are practically available to homeless individuals for reasons beyond religious coercion. Many functional barriers to shelter deprive homeless individuals of a meaningful choice, and the Eighth Amendment prevents governments from punishing individuals for matters beyond their control. Courts should make individualized inquiries when considering the constitutionality of criminalization measures to assess whether individuals experiencing homelessness truly have a meaningful “choice” in sleeping outside. However, the constitutional infirmities behind criminalization measures, the highly factual inquiries required of courts to determine their constitutionality, and their exacerbation of homelessness underscore the need for cities to stop criminalizing homelessness.