2010
Following an investigation into whether a violent altercation between Portwood and ex Gary Shirley that aired on Teen Mom merited criminal charges, prosecutors arrested the reality TV star and filed two felony counts of domestic battery, one felony count of neglect of a dependent and one misdemeanor count of domestic battery. As part of a plea deal, Portwood plead guilty to two counts and was placed on two years probation.
2011
Portwood was taken into custody for felony possession of a controlled substance and ultimately charged with violating her probation. She spent the holidays behind bars, and in Feb. 2012 agreed to complete a court-ordered drug treatment program. If unable to stay out of trouble, Portwood would face a 5-year prison sentence.
2012
In March 2012 Portwood failed a drug test and dropped out of her treatment program by choice. Her five-year sentence was reimposed in its entirety, and she turned herself in three months later.
2013
Portwood was released from an Indiana jail in Nov. 2013, spending less than two years behind bars after earning "good time credit" for participating in a substance abuse program and exhibiting good behavior.
2015
By 2015, Portwood had turned her life around. She told E! News in an interview, "I think I've changed a lot. It's hard to think about the past because I can't remember half of it. Now, [I'm] living a sober life and trying to do good things. I'm trying to be normal."
2019
The 29-year-old was arrested in Indiana on a domestic battery charge following an alleged incident between her and a male victim. The man identified himself as Portwood's live-in boyfriend Andrew Glennon, and told authorities she assaulted him while he was holding their 1-year-old child.