Season 2 picks up nine months after Ashley and Miles' prison nuptials in the season one finale as Ashley is trying and raise their son on her own. She is reaching her breaking point and is taking it out on everyone around her. Miles is adjusting to life on the inside and counting down the days before their first family visitation weekend at San Quentin.

Rainey is doing her best to make Ashley and Sean feel at home while trying to stay connected to her son behind bars, but Ashley holds all the cards. Trish's new business is flourishing, but she is dealing with jealousy issues now that her best friend and business partner Jacque is dating Cuddie.

Janelle is growing frustrated with Ashley's constant need for support and has begun to miss her life back in Bali. Earl, fresh out of prison himself for unintentionally breaking his probation, has moved out of Nancy's house and is trying to re-establish a relationship with his own family, and his past.