In March 2009, File Under: Music released another EP called Roboteering, containing songs from Mangan's forthcoming album Nice, Nice, Very Nice. The album was recorded in Toronto at Green Door Studios with producer John Critchley, and featured an assortment of other Canadian artists such as Veda Hille, Justin Rutledge, Mark Berube, Hannah Georgas and members of Said The Whale, Major Maker, and Elliott Brood. Five months later, Nice, Nice, Very Nice was released in Canada. The album name was inspired by a line from American novelist Kurt Vonnegut's book Cat's Cradle, while musically Nice, Nice, Very Nice has been compared to Chad VanGaalen and Bon Iver. The first two singles from his second full-length, "Robots" and "Road Regrets" earned airplay on local Vancouver radio stations, as well as on satellite radio stations such as The Verge and CBC Radio 3.
In September 2009, Mangan was awarded "Artist of the Year" at the Verge Music Awards. In 2010, Nice, Nice, Very Nice was licensed and released by Toronto-based independent record label Arts & Crafts in the United States and Europe (via City Slang). The album was shortlisted for the Polaris Music Prize. Nice, Nice, Very Nice was also awarded "iTunes Album Of The Year" for the Singer/Songwriter category and won three Western Canadian Music Awards for "Independent Album Of The Year", "Roots/Solo Album Of The Year" and "Songwriter Of The Year". "Robots" was named "Best Song" by the CBC Radio 3 BUCKY Awards.