Many kings of Jaffna, such as Cankili I, initially confronted the Portuguese in their attempts at converting the locals to Roman Catholicism, but eventually made peace with them.

Eventually, a usurper named Cankili II resisted Portuguese overlordship only to find himself ousted and hanged by Phillippe de Oliveira in 1619.

[1] The Jaffna kingdom came to the attention of Portuguese officials in Colombo for multiple reasons, which included their interference in Roman Catholic missionary activities (which was assumed to be supporting Portuguese interests), the lucrative markets and strategic benefits of Jaffna's Vannimai chieftaincies, and their support of anti-Portuguese factions within the Kotte kingdom, such as the chieftains from Sitawaka.

[1] By the late 16th century, Portuguese influence strengthened in the courts of the Kandyan and Kotte kingdoms and some of Jaffna's Vannimai chieftaincies were subdued by these kings.

They gained access to the seaports of Trincomalee and Batticaloa in the east, but the Jaffna peninsula proved more convenient as an entry port for military aid arriving from South India.

[1][2] In 1591, during the second expedition, led by André Furtado de Mendonça, King Puvirasa Pandaram was killed and his son Ethirimanna Cinkam was installed as the monarch.

This arrangement gave the Catholic missionaries freedom of action and monopoly in elephant export to the Portuguese, which the incumbent king, however, resisted.

The remaining captives were asked to become monks or nuns in the holy orders, and as most obliged, their celibacy avoided the production of further claimants to the Jaffna throne.

[13] At the time, the mainland south of Elephant Pass was claimed by the King of Kandy, Senerat; he and his troops were consistently harassing the Portuguese in the Jaffna Peninsula.

Two were led by Migapulle Arachchi,[11][15] during that period, Portuguese destroyed every Hindu temple[16] and the Saraswathy Mahal library in Nallur, the royal repository of all literary output of the kingdom.