April 2024 marks the 20th anniversary of Baltic NATO membership. This symbolic milestone offers an opportunity to take stock of the Baltic security landscape and discuss what has been achieved over the last two decades and what challenges still lie ahead. Russia’s war in Ukraine has upended the once hopeful vision of the Baltics as a tension-free geopolitical space, thus giving way to confrontational and escalatory dynamics. The previous NATO tripwire logic, with a modest multinational force presence, is no longer viewed as sufficient. Instead of placing faith in the policy of military reinforcement, the Baltic states are now actively calling for a robust allied presence on the ground. In light of this, the Riga workshop, by gathering lead scholars and practitioners, seeks to tackle the following key questions: What are the baseline requirements for credible deterrence on NATO’s eastern flank? Are the Baltic states ready to accommodate a brigade-size allied presence? What is the role of women within small-state armed forces such as the Baltics and how have they faired in implementing NATO’s Women, Peace, and Security agenda? The event, consisting of two scholarly panels and a policy roundtable, will be of interest to policy practitioners, international relations students, and the broader audience.