She went to the University of the West Indies at Cave Hill in Barbados, graduating with a bachelor's in law in 1984.
She obtained a legal education certificate from the Norman Manley Law School in Jamaica in 1986.
[1] Webster first entered politics in 2010, running for the Island Harbour seat in the House of Assembly as a member of the Anguilla Progressive Party.
[5][6] Alongside Cora Richardson-Hodge and Evalie Bradley, she was part of a wave of female candidates who took office in the House of Assembly that year, the first women to do so in over three decades.
[9] She ran for re-election to the House of Assembly in 2020 but lost to the leader of the Anguilla Progressive Movement, Ellis Webster, who became prime minister.