Von der Osten debuted in 1902 at the Dresdner Hofoper and performed there regularly until the end of her career.
Von der Osten also was active as an opera director and served in that capacity for the premiere performance of Richard Strauss’s Arabella.
Von der Osten’s career led to guest appearances in many of Europe’s leading opera houses.
From 1923 to 1924, she found great success in the female roles of Richard Wagner—particularly that of Isolde in Tristan und Isolde—while touring with director Leo Blech’s “German Opera Company” in North America.
Von der Osten died in 1936 at her estate at Talmühlenstraße 49 in Kurort Hartha (today: Tharandt).