On October 22, 2018, the Town of Windsor received a letter from the law firm of Shenkman & Hughes alleging a violation of the California Voting Rights Act ("CVRA"). The letter claimed that the Town's current at-large election system dilutes the ability of Latino voters to elect candidates of their choice or otherwise influence the outcome of Town Council elections. The letter also threatened litigation if the Town declines to voluntarily change to a district-based election system. 

Over a series of public hearings and community meetings held in February and March 2019, the Town Council discussed and developed four Town Council district boundaries for the transition to District-based elections. The four districts are in compliance with the California Voting Rights Act, which requires that each district have a population within +/- 5% of 6,700 – the ideal population for each of the four districts. At their regular meeting on April 3, 2019, Council adopted Ordinance No. 2019-332, amending title 1, chapter 2 of the Code of the Town of Windsor to establish a district-based election system for four districts and an at-large elected Mayor. At the September 4, 2019 Town Council meeting, the Town Council adopted Ordinance No. 2019-336, amending Windsor Municipal Code Figure 1-2-200(A) of Title 1, Chapter 2, Article 2 "District Elections," to incorporate newly annexed territory into Windsor Town Council District 2. 

The Town of Windsor began transitioning from at-large to district-based elections with the November 3, 2020 election.

Sequencing
Sequencing for the transition to district-based elections will occur as follows.  A member of the Town Council shall be elected from Town Council District 3 at the November 2020 general municipal election, and every four years thereafter.  Members of Town Council shall be elected from Town Council Districts 1, 2 and 4 at the 2022 general municipal election, and every four years thereafter.  The Mayor shall be elected at-large, beginning at the 2020 general municipal election and every two years thereafter.