Incumbent Helir-Valdor Seeder who has declared he will run for re-election, is up against a challenge from former prosecutor general Lavly Perling, who heads up an Isamaa faction known as the Right-wingers (Estonian: Parempoolsed), which despite its name broadly refers to party members on the more socially-liberal end of the Isamaa spectrum. The Parempoolsed emerged last year at a time when Isamaa was in office with the Conservative People's Party of Estonia (EKRE) and was ostensibly opposed to populism. Since then, the party has found itself in opposition, while one of the points of controversy, a planned referendum on the definition of marriage, was canned with the entry into office of the Reform/Center coalition in January.

The convention takes place at the Tartu Song Festival Grounds on June 20. Earlier reports that the convention would be postponed until after the October 17 local elections, a move which would have granted Helir-Valdor Seeder an extra year in charge on top of his regular term, was met with opposition.

The party has faced internal division and upheaval, including a recent, failed attempt at a corporate join-up by a right-wing, in the regular sense, group, Rahva tahe, which would have added over 500 new members, and Seeder has in recent months called for internal critics to be expelled from the party.

The June 20 convention will also host elections for the party's governing board, its court of honor – the body which oversees behavior of members among other aspects of party life and its review committee.

Several leading Isamaa members are in the running for the board, incuding MPs Viktoria Ladõnskaja-Kubits, Aivar Kokk and Priit Sibul – the latter heads up the party's Riigikogu group – and former government ministers Raivo Aeg, Tõnis Lukas, Marko Pomerants, Urmas Reinsalu, Riina Solman and Sven Sester. In total 34 people are running, with 20 positions to fill.

Sixteen leading party members are running for posts in the nine-person court of honor, while only one more individual is running for the review committee than there are positions (five) to fill.

Lavly Perling was prosecutor general October 2014-October 2019, and acting prosecutor general for a few months thereafter, until Andres Parmas took up the post in February last year.

Isamaa regularly polls around the 5 percent mark, a signal figure in that it is also the proportion of votes needed in a constituency to pick up seats, under Estonia's modified d'Hondt system of proportional representation. The party has polled at such levels in the past in the months leading up to elections, however, and still emerged with seats, for instance before the March 2019 general election.

The party recently proposed a vote of no-confidence in defense minister Kalle Laanet (Reform) in response to recently announced defense spending cuts.

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