Milestones contains eleven songs, all but one of which are previously released. Five of them, including Dunn's self-penned well-beloved hit "Daddy's Hands", were originally released in the late 1980s by independent label MTM Records. Four more, including her two #1 country hits "Are You Ever Gonna Love Me" and "You Really Had Me Going", were originally put out by Warner Bros. Nashville, which signed Dunn after MTM closed its doors in late 1988 and acquired her MTM masters. In addition, "A Face in the Crowd" — a duet with Michael Martin Murphey that appeared in the latter's thirteenth studio album Americana (1987), also released by Warner Bros. — and the controversial "Maybe I Mean Yes", a brand-new song, also make their appearances in Milestones.
Two singles were released from the album: "Maybe I Mean Yes" and "No One Takes the Train Anymore", which was previously an album track from Dunn's fourth studio album The Blue Rose of Texas (1989). The former peaked at #48 on the BillboardHot Country Singles & Tracks chart.[2]