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Although New York City had shown increased attention to coastal flooding since Superstorm Sandy in 2012, much less attention had been given to fluvial, or rainfall, flooding, until 11 New Yorkers drowned in their basement apartments during Hurricane Ida in September 2021. This study interviews 22 households in basement apartments or in homes with basements that have experienced flooding. We find that complex social problems, or "wicked problems" are complex and wicked all the way down, from the municipal scale to the individual basement. Features of rain flooding make it surprisingly dangerous, and particularly difficult to address. This paper documents the diverse uses of basements as residences, and residents' experiences during and after flooding, to demonstrate that detailed understanding of the uses of basement housing must be taken into consideration when considering policies to address rain flooding and basement flooding.