Born on 12 November 1889 in Bratucice near Okulice, the son of Błażej and Anna, née  Korcyl. In 1904, he became a member of the Riflemen's Association (Polish: Związek Strzelecki). In October 1915, he left school and volunteered for the Polish Legions Infantry Regiment. After the Oath Crisis, he was conscripted into the Austrian army, from which he deserted before devoting his effort and time to organising the structures of the Polish Military Organisation (Polish: Polska Organizacja Wojskowa, POW) in the poviat of Bochnia.

He volunteered for the reborn Polish Army and, as a soldier of the 4th Polish Legions Infantry Regiment, his fighting experience included the defence of Lviv and the Polish-Bolshevik war. His bravery and tactical skills demonstrated during fighting near the village of Zaręba earned him the Silver Cross of Virtuti Militari, presented on 1 June 1920 by Marshal Józef Piłsudski.

After the end of military operations, he stayed in the Polish Army. In 1935, he was transferred to the General Staff, where he took up the post of Head of the East Department in Branch III. Until the spring of 1939, he was involved in preparing the Polish Army’s action plans in case of war with the Soviets.

During the September Campaign, he fought in the defence of Warsaw, and was awarded the Gold Cross of Virtuti Militari for his actions while defending the capital. On 27 September, he became a soldier of the Service for Poland’s Victory (Polish: Służba Zwycięstwu Polski, SZP), and later of the Union for Armed Struggle (Polish: Związek Walki Zbrojnej, ZWZ) He took command of field structures in Łódź, but when this was exposed he was forced to leave for the Soviet occupation zone in October 1940, and was captured there by the NKVD in January 1941. He was interrogated in Lviv prison by Lavrentiy Beria and Ivan Serov, then transferred to Moscow and subjected to a brutal investigation. In August 1941, after the Sikorski-Mayski Agreement had been signed, he was released from prison. General Władysław Anders appointed him Chief of Staff of the Army and then gave him command of the 7th Infantry Division with which Okulicki was evacuated to Persia. When staying there, he decided to return to Poland and continue fighting in the underground.

In May 1944, he landed outside Wierzbno, near Cracow, and made his way to Warsaw where he was assigned to the Home Army Headquarters. During the Warsaw Uprising, he inspected barricades, visited soldiers, comforted them and encouraged them to continue their efforts. It was then that he was awarded the Order of Virtuti Militari for the third time, with a Gold Cross for the second time.

When the decision was made to surrender, General Tadeusz Komorowski ordered Okulicki to remain in the underground and entrusted him with command of the Home Army. He was credited with overcoming the crisis of the underground army which had suffered heavy losses at the hands of the Germans and Soviets. He also devoted a great deal of attention to supervising the establishment of the cadre organisation called “Independence” [Polish: Niepodległość] (codenamed “NIE”) which General  “Nil” August Emil Fieldorf had been in the process of organising for many months. This deeply hidden structure was to gather personnel capable of surviving under the conditions of the Soviet occupation.

In his order dated 19 January 1945, he dissolved the Home Army. He himself stayed underground because, in his opinion, it was only under deep cover that NIE could fight effectively against the new occupant.

In February 1945, the Soviets proposed that negotiations could be started with the leaders of the Polish Underground State. At the end of March, in Pruszków near Warsaw, Okulicki met General Ivan Serov from the NKVD whom he had already known from the Brygidki prison in Lviv. Together with other leaders of the Polish Underground State, he was arrested and deported to Moscow, despite the security guarantees given by the Soviets. In June 1945, the leaders of the Polish Underground State underwent a show trial in Moscow. General Okulicki was sentenced to 10 years imprisonment, which was the highest sentence passed at that time. However, he spent only a year and a half in a Soviet prison. He died on Christmas Eve 1946 in unexplained circumstances.