She debuted in After School's sub-unit Orange Caramel on June 18, 2010, on KBS Music Bank with the song "Magic Girl".

On June 12, 2014, Raina and rapper San E released an R&B duet called "A Midsummer Night's Sweetness".

On June 5, 2017, Raina released her third OST titled When Rain Falls for MBC's drama Lookout; fellow After School member E-young participated in lyric-writing, composition and arrangement for the track.

Subsequently, on September 5, 2018, Raina's soundtrack single entitled "Home" was released as the fifth OST for SBS' drama Your Honor.

[11] To much excitement of fans, Raina released her next OST for KBS's Once Again alongside former Myteen member and Produce X 101 contestant Song Yuvin, called "Love is Danger".

[12] Since then, Raina has been announced as part of the line-up for MBN's female idol revival show Miss Back hosted by Baek Ji-young.