He made his Broadway debut in 2019 playing Phoenix in the musical Jagged Little Pill, a role he originated at the American Repertory Theater.

My Baby; the award recognizes "outstanding achievement in individual artistry, vocal, dance and acting performances for a male lead in a high school musical theatre production.

[6][7] In 2018, he was cast in the original Cambridge, Massachusetts, production of the musical Jagged Little Pill, inspired by the album of the same name by Alanis Morissette.

[12] Cipriano did not rejoin the production in September 2021 due in part to his stance on the controversy surrounding the musical's main character Jo, whose gender was changed from non-binary to cisgender for the Broadway version.

[13] In October 2020, it was announced that Cipriano would start opposite Belle Shouse and Stephen Moyer in the supernatural horror series Safehaven.