The album was reissued in an remastered and expanded 25th anniversary edition on August 28, 2020. The release also features a live album, "Live at Umbra Penumbra", a 1994 performance at a Portland café, thought to be the earliest-known live recording of Smith performing as a solo artist. As part of the anniversary edition, J.J. Gonson, the artist behind the "Elliott Smith" album cover, released a 52-page coffee table book with handwritten lyrics, words from Smith's peers about the album's creation, and a series of previously unseen photographs. Gonson released a series of photo prints of Smith, one per month through August 2020, available for purchase through Morrison Hotel Gallery.