Simon V was the fifth child and eldest son of Bernard VII "the Bellicose" and Anna of Holstein-Pinneberg and inherited Lippe after his father's death, around 1511.

An open conflict arose in 1530 when Protestant hymns were sung during a Catholic Easter Mass.

Simon, who remained a Catholic all his life, was outraged, and spoke of insurgent farmers who refuse to endure any authority over themselves.

Philip of Hesse urged the citizens of Lemgo to redress their dispute with Simon V; nevertheless, Lutheranism continued to spread in the cities.

In 1535, Simon V and Duke John III of Cleves invaded Lippstadt, which had turned Protestant.