It fought as part of 17th Army (Carl-Heinrich von Stülpnagel) in the Vinnytsia area and participated in the Battle of Uman.

It crossed the Dnieper and took part in the German advance through Ukraine before facing a setback during the Soviet winter offensive of 1941.

[2] The 295th Division also the Mobile Group of the First Slovak Republic, Slovakia's most significant contribution to Operation Barbarossa.

[4] In August 1941, members of the 295th Infantry Division either actively participated or at least in the majority passively stood by during a massacre of civilians in Bila Tserkva, a Ukrainian settlement close to Kiev.

The divisional first staff officer, Helmuth Groscurth, was unable to prevent the village's young children from falling victim to the SS.