At the outbreak of Operation Barbarossa, Boldin was the deputy of Gen. Dmitry Pavlov, commander of the Western Military District. Both men saw clear indications of the impending attack, but their warnings to the High Command were ignored. Late on June 22, Pavlov ordered Boldin by phone to mount a counter-attack against German forces advancing on Grodno. Boldin flew in a light aircraft under heavy fire to the command post of 10th Army near Bialystok. In the prevailing chaos it was impossible to carry out any effective attack, and by June 27 the 3rd, 4th and 10th Armies were all encircled west of Minsk. Boldin, at the head of a small group, spent the next 45 days fighting for survival behind enemy lines. Finally, on August 10, leading a total of 1,650 officers and men, his group broke through to Soviet lines near Smolensk. "STAVKA" Order No. 270 praised the feat of Boldin's "division", and he became a popular hero in those dark days.