Also known as I Take A Chance Every Time, this album was released in an incredibly limited hand-made CD-R edition on band member Juan Garcia's Little Hands label in late 2000.

Taking a step back from the upbeat pop of the full-band recordings from this time, Cruel August Moon is a collection of far quieter reflective bedroom slowcore. The sound is much closer to the patient folk of Flashpapr, all the members of whom play on this record.

Jessica Bailiff, Erika Hoffmann and Risa Buberniak also lend female vocals to this quiet, sad dream of a record.