Cunningham first entered politics as a member of the Templeton Unified School District Board of Trustees before successfully running for the California State Assembly in 2016.

[2] Cunningham introduced AB (Assembly Bill) 2385, which urges publishers to provide a detailed description of how newer versions of their materials differ from older ones,[3] and AB 2580, which requires hearing officers to grant requests for hearing extensions by applying a specified standard of "good cause” in due process cases pertaining to special education matters.

[4] He co-introduced AB 1743, permanently funding the Career Technical Education Incentive Grant (CTEIG) which aims to equip students with necessary skills for the future economy.

[9] AB 653, introduced by Cunningham and signed into law authorizes a Santa Barbara County nonprofit hospital to enter into a joint powers agreement with a public agency.

[14] Cunningham, along with other Central Coast Legislators worked to lessen the impact from the closure of the Diablo Canyon Nuclear Power Plant.

Cunningham and State Senator Bill Monning authored legislation that would address unemployment after the closure of the plant by providing job assistance programs to former employees.

Cunningham also worked on legislation that provided an $85 million settlement for San Luis Obispo County to address impacts from the closure.