Among his most important proposals were abandoning the defence of the northern frontier to concentrate forces in the mountainous interior re-organizing the armed forces into Serb, Croat, and Slovene units in order to better counter subversive activities and using mobile Chetnik units along the borders.

His military career almost came to an abrupt end in 1939, when he submitted a report strongly criticizing the organization of the Royal Yugoslav Army. He was then appointed as an attaché to Czechoslovakia in Prague. Mihailović then came in contact with members of Zveno and considered taking part in a plot which aimed to provoke Boris III's abdication and the creation of an alliance between Yugoslavia and Bulgaria, but, being untrained as a spy, he was soon identified by Bulgarian authorities and was asked to leave the country. On September 6th, 1935, he was promoted to the rank of colonel. In 1935, he became a military attaché to the Kingdom of Bulgaria and was stationed to Sofia. Some authors claim that he met and befriended Charles de Gaulle during his stay, although there is no known evidence of this. That same year, he spent three months in Paris, following classes at the École spéciale militaire de Saint-Cyr. He was promoted to the rank of lieutenant colonel in 1930. In 1923, having finished his studies, he was promoted as an assistant to the military staff, along with the fifteen other best alumni of his promotion. In 1921, he was admitted to the Superior Military Academy of Belgrade. Following the war, he became a member of the Royal Guard of the Kingdom of Serbs, Croats and Slovenes but had to leave his position in 1920 after taking part in a public argument between communist and nationalist sympathizers. He later received several decorations for his achievements on the Salonika Front.

He served in World War I and was involved in the Serbian Army's retreat through Albania in 1915. At the end of the Second Balkan War, during which he mainly led operations along the Albanian border, he was given the rank of second lieutenant as the top soldier in his class, ranked sixth at the Serbian military academy. He fought as a cadet in the Serbian Army during the Balkan Wars of 1912–13 and was awarded the Silver Medal of Valor at the end of the First Balkan War, in May 1913. As both of his uncles were military officers, Mihailović himself joined the Serbian Military Academy in October 1910. Orphaned at seven years of age, Mihailović was raised by his paternal uncle in Belgrade. Dragoljub 'Draža' Mihailović was born on April 27th, 1893 in Ivanjica, Kingdom of Serbia to Mihailo and Smiljana Mihailović.

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