Major Di Milia joined the Italian Air Force Academy in August 2004, where he obtained a degree in Political Science. In 2009, he started military pilot training at the Specialized Undergraduate Pilot Training School in Vance AFB (US). He later obtained ‘Combat Readiness’ on the C130 aircraft at the Air Transport Squadron of 46th Air Brigade in Pisa. From 2011, he complemented his training with special skills, e.g. airdrop, air-to-air refuelling, night-vision goggle flight, and assault operations. As a pilot, he was extensively involved in air support missions abroad in Afghanistan 2011–2015, Kosovo 2012, Lebanon 2013, Libya 2014, and Iraq 2014. Furthermore, he participated in a plethora of multinational joint exercises. Since September 2019, he has served in the JAPCC as the Subject Matter Expert for Air Transport.