[6] In February 2008, Freeman released the initial version of Cydia, a software distribution and installation tool for jailbroken iOS devices.

[11] He has developed a plethora of software extensions for jailbroken iOS users to add features to iOS, including Apple File Conduit 2,[12] Cycorder,[13] CyDialer,[14] Cydget,[14] Cyntact,[15] Cyueue,[16] Five Icon Dock, Veency,[17] and WinterBoard.

[21] In April 2013, he built an implementation of a root (jailbreak) for Google Glass[22] and published an analysis of the ramifications.

[26] In January 2016, he announced his candidacy for the Santa Barbara County Board of Supervisors,[27] and in June 2016 he lost in the primary election for that role.

[28] He then ran for a four-year seat on the board of directors for the Isla Vista Community Services District and was elected in November 2016.