Grandniece of the Decembrist Pyotr Kakhovsky, she was a representative of the Left Socialist-Revolutionaries during the Russian Revolution: in 1918 she organized the assassination of Field Marshal Hermann von Eichhorn, commander of the German occupation forces in Ukraine.

[1] In total she spent forty-five years of her life in prison and exile, both under the Tsarist and Soviet regimes, as well as briefly at the end of World War I in German military jail.

Probably thanks also to her acquaintance with Alexandra Kollontai,[2] for some time she supported the ideas of social democracy and briefly sided with the Bolsheviks in Saint Petersburg, becoming secretary of their local district organisation.

[2] After the outbreak of the 1917 February Revolution, the other political prisoners from the Nerchinsk Katorga were released as well and she collaborated with Maria Spiridonova in the creation of the Chita Committee of the Party of Socialist Revolutionaries.

[2] During June, Kakhovskaya and Donskoy conducted surveillance, trying to establish the most successful time and place for the murder of the German Marshal, who was considered a ruthless tyrant.

After her return to Moscow, she too suffered from typhus and was arrested again at the beginning of 1921: despite the fact that she was already sitting in Butyrka Prison during the Kronstadt rebellion, she was found guilty of complicity in it and sentenced to exile in Kaluga[11] in 1922.

A special session at the Collegium of the Joint State Political Directorate (OGPU) condemned Kakhovskaya to 3 years in a concentration camp with a replacement for expulsion to Vyatka for the same period.

Their term of exile having been extended, in 1928 Kakhovskaya, Izmailovich and Spiridonova moved to Tashkent, where they earned a living by technical translations from English, and gave private lessons.

In the early 1930s, they were re-arrested and exiled to Ufa,[10] where they formed a sort of commune, also including Spiridonova's husband, Ilya Mayorov, his invalid father and teenaged son, and Kakhovskaya's elderly aunt.

In February 1937, the whole group was hauled in by the NKVD and detained for several months under the charge of havig attempted to create a united counterrevolutionary centre and having carried out terrorist acts against the Communist leaders of Bashkiria.

[13] While they were held and subjected to harsh interrogations, however, "the entire Bashkir government itself was arrested, so charges of plots against Stalin and Politburo member Klementi Voroshilov were substituted.

"[14] On 25 December 1937, in a closed session of the Military Collegium of the Supreme Court of the Soviet Union on the fabricated case of the All–Union Socialist Revolutionary Center, Kakhovskaya was sentenced to 10 years in prison.

In 1954, she was released from exile and, next year, she moved to Maloyaroslavets, where she was engaged, among other things, in translating the fairy tale by Antoine de Saint-Exupéry The Little Prince (unpublished).

In November 1958,[15] at the age of 71, she would have a memoir she called Notes and Explanations ("Zapiski i Zaiavleniia") sent on to the Central Committee of the Communist party, to the Council of Ministers, and to the Office of the Public Prosecutor, with the sole aim of keeping alive the memory of her comrades' late years.