Helmut Oberlander was born on February 15, 1924 in Halbstadt, a Russian Mennonite settlement in what is now Zaporizhzhia Oblast, Ukraine.

During the Second World War, he served in the Waffen-SS and acted as an interpreter for the Einsatzkommando 10a. He was also a member of the Sicherheitsdienst and Sicherheitspolizei. The Einsatzkommando was a mobile killing squad in Nazis Germany responsible for the deaths of thousands of people during the war. Oberlander maintains he was forcibly conscripted into military service and that his duties only included translating Russian radio transmissions, acting as an interpreter, and guarding military supplies.

Oberlander immigrated to Canada in 1954 and settled in the Kitchener-Waterloo area. He opened a construction business and became a Canadian citizen in 1960.

The Government of Canada initiated a denaturalization and deportation process against Oberlander in 1995 for not disclosing his wartime record during his immigration interview in 1953. Between 1995 and 2018, numerous court orders were filed to strip Oberlander of his citizenship. Oberlander consistently appealed these orders.

In 2000, Judge Andrew Mackay concluded that while Oberlander may not have disclosed his wartime record there was no evidence proving he was involved in committing any war crimes or crimes against humanity.

In 2017 the Government of Canada stripped Oberlander of his citizenship for a fourth time through an Order in Council. In 2018, the Federal Court ruled that this revocation was lawful. Oberlander's appeal was dismissed in the Federal Court of Appeal in April 2019. The Supreme Court of Canada declined to grant Oberlander's leave to appeal the Federal Court decision December 2019. In 2020, Oberlander also lost his appeal to the Immigration and Refugee Board.