From at least 1888 onwards, Anna was Nikolai Orelov's wife, and was fully aware of her husband's Assassin background. As such, she would seek to calm him when Nikolai felt guilt over the death of his friend and brother, Aleksandr Ulyanov.
During 1888, Anna was several months pregnant with her and Nikolai's first child. However, the baby died before birth; a grievous blow to the Orelov family, which caused Nikolai to become bitter and filled with hate.
Between 1908 and 1917, Anna gave birth to Nikolai's first surviving child, a daughter they named Nadya, and the two were present with Nikolai when he exhumed the body of Grigori Rasputin.
In 1917, Anna, Nikolai, and Nadya fled Russia. They boarded a boat bound for the United States, where they started a new life together. Some time later, Anna gave birth to a son, who she and Nikolai named Innokenti.
During the Palmer Raids of 1919, while Anna and her family were in a local bar, federal officers arrived and began to round up Russian immigrants. In the ensuing chaos, Anna and Nadya were separated from Nikolai and Innokenti, and were deported back to Russia. The Assassin Brotherhood later claimed that they had ensured Anna's and Nadya's safe arrival in Russia, to protect "their own".