Insight Out saw the band mixing their textured vocal harmonies with an eclectic blend of influences, including Baroque pop, folk rock, sunshine pop, psychedelia and even elements of garage punk. Along with the hit singles "Windy" and "Never My Love", standout tracks on the album include P. F. Sloan's reflective "On a Quiet Night", the Addrisi Brothers' "Happiness Is", and the band originals "We Love Us", "When Love Comes to Me", and "Requiem for the Masses". The latter song in particular was an ambitious and somber piece written by multi-instrumentalist Terry Kirkman, featuring layered Latin vocals and recounting the story of a matador dying alone in the bullring, miles away from his home. As such, the song was intended by Kirkman to strike parallels with the plight of U.S. soldiers serving in the Vietnam War and to function as a veiled protest against that conflict.
Music critic Matthew Weiner, writing for Stylus magazine, has described Insight Out and its follow-up Birthday as "minor classics in the late-sixties pop genre", while music historian Richie Unterberger viewed the album, within the context of The Association's back catalogue, as "characteristically eclectic". In his review for the Allmusic website, Bruce Eder has described Insight Out as "an enjoyable folk-rock album", but also noted that the LP was recorded "somewhat in the shadow of Harpers Bizarre's experimental "Feelin' Groovy" single.
Insight Out has been reissued a number of times on CD, including a remastered edition of the album in its standard stereo configuration on Collectors' Choice Music in 2003 and as a Japanese release on Warner Bros. in 2005, with the addition of two bonus tracks. In 2011, Insight Out was reissued in a deluxe CD package by Cherry Red Records, featuring the original mono mix of the album and multiple bonus tracks.