In late June 1941, Nazi Germany stormed the borders of the Soviet Union, occupying the three Baltic republics within weeks. By the end of 1941, a significant proportion of the Jewish population had been murdered by German forces and local collaborators. In the days before full Nazi occupation of the territory, Latvia's Jews confronted the question of whether to flee into the Russian interior or stay in their communities. History shows that this would be a critical choice. Testimonies and memoirs of Jewish survivors illuminate the competing motivations to leave or to remain. This article highlights the key factors that figured into these calculations and the interaction between individual agency and structural opportunities and obstacles in determining where Latvia's Jews were when Holocaust in their homeland began.