Volunteering to fight in the Waffen—SS for the Nazis in February 1944, Käärmann was among those who fought the Red Army until Estonia was occupied by the Soviets seven months later.
At the end of the war, the Soviets conducted extensive sweeps to arrest and deport the many Estonians who had served in the German Waffen-ss.
Wanting to avoid the fate of his brother, who was arrested and sent to Russia's most dreaded Arctic prison camp near Vorkuta, Käärmann returned home to his family farm on October 4, 1944.
Ten days later, after a message was sent via a Latvian Forest brother, a nurse from Latvia came secretly to the house and amputated his badly injured arm.
The Estonian Minister of Defence, Jaak Aaviksoo, awarded the Cross of Merit [et] (third class) on September 10, 2007, to Alfred Käärmann for his part in the struggle to establish Estonia’s sovereignty.