Ivan Annenkov received a home education and attended lectures at Moscow University in 1817 and 1819, but did not complete the course. After passing the exam at the General Staff on August 10, 1819, he was accepted into the Life Guards Cavalry Regiment as a junker. From November 1, 1819, he became an estandart-junker, then a cornet, and from December 21, 1819, a lieutenant, with the rank confirmed on March 13, 1823. Among his friends were many future Decembrists, such as P. N. Svistunov, F. F. Vadkovsky, and A. M. Muravyov. He spent his childhood and youth in his mother's house in Moscow at the corner of Petrovka and Kuznetsky Most.

On December 14, 1825, Annenkov was on Senate Square, but he sided with the government, commanding a platoon of cavalry guards protecting the artillery. After the uprising was suppressed, he was arrested and sentenced to 20 years of hard labor, loss of rank and nobility, and lifelong exile in Siberia.

Six months before the uprising, Ivan Alexandrovich met Polina Göbl, the daughter of a Napoleonic officer, who came to Moscow to work as a milliner. In the summer, they met at a fair in Penza. The Annenkovs had estates in the Simbirsk, Penza, and Nizhny Novgorod provinces, and under the pretext of visiting them, the young people made a short trip. In one of the villages, Ivan arranged with a priest for their wedding, but Polina refused out of fear of her mother. In November 1825, they returned to Moscow. The uprising shattered their plans. Polina made it to Chita, where she married Ivan Alexandrovich in the wooden Mikhailo-Arkhangelsk church. At the time of the wedding, his shackles were removed.

Only thirty years later, in 1856, the Annenkovs received permission to leave their place of exile. They were prohibited from living in St. Petersburg and Moscow, so they settled in Nizhny Novgorod in June 1857. Ivan Alexandrovich was appointed to a special assignments position under the Nizhny Novgorod governor. He passed away on January 27, 1878.