AllMusic called Strays Don't Sleep "a small gem of an album."[2]The Skinny wrote: "It's a nice enough collection of songs, drawing on every last trick from the melancholy-acoustic textbook, the only trouble is that not one of the nine songs on offer raises the stakes beyond average."[3]Paste wrote that "from its dark, understated melodies and instrumentation to its elegant production, this record is an archetype for urban folk music."[8]The Sunday Times called the album "a work of fragile, studio-bound electronica."[6]
"For Blue Skies" Directed by Matthew Ryan, Neilson Hubbard; Shot, Edited by Matt Riddlehoover, Neilson Hubbard, Matthew Ryan; Featuring Mark Cabus The Film Inside The Film – Directed by Abe Bradshaw, Edited by James "Buddy" Villani
"Spirit Fingers" Directed by Jared Johnson
"April's Smiling At Me" Directed by Matt Boyd
"Cars And History" Directed by Gorman Bechard; Featuring scenes from his film You Are Alone
"Falling Asleep With You" Directed by Matthew Ryan; Shot by Lauwrence Boothy, Tonie Floyd; Edited by Rich Jegen, Kenny Bernstein
"Pretty Girl" [Bonus Version] Directed by Matt Boyd