84 Wing, the squadron was formed in August 1999 to train the RAAF's Lockheed Martin C-130J Hercules aircrew and ground support staff.

285 Squadron did not control any flying aircraft but managed the flight simulator used for converting aircrew to the C-130Js operated by No.

It was also allocated decommissioned Hercules airframes for training purposes, as well as flying aircraft from No.

285 Squadron was located at RAAF Base Richmond in the western suburbs of Sydney.

285 Squadron was responsible for training aircrew and maintenance staff to operate the Lockheed Martin C-130J Hercules transport aircraft of the Royal Australian Air Force (RAAF).

[4] The aircraft are generally crewed by two pilots and a loadmaster, and tasked with medium tactical airlift in Australia and overseas, transporting troops and cargo, and conducting medical evacuation, search-and-rescue, and airdrop missions.

285 Squadron managed the full-flight mission simulator (FFMS) used to convert aircrew to the C-130J, as well as decommissioned Hercules airframes used for loadmaster training.

It culminated in an airborne operation module, which included formation flying, airdrops, night landings with night-vision goggles, and simulated combat utilising the C-130's self-defence systems to prepare the aircrew for conditions in Middle East deployments.

[12] The squadron began operating a full-flight mission simulator (FFMS) for the C-130Hs in 2003, coinciding with the deployment of C-130Hs to the Middle East.

Replacing a more basic C-130H simulator, the FFMS was used to train pilots, navigators and flight engineers.

36 Squadron transferred its C-130Hs prior to re-equipping with Boeing C-17 Globemaster III heavy airlifters and relocating to RAAF Base Amberley, Queensland.

285 Squadron was named the most proficient RAAF training unit of the previous year.

[19] The C-130J FFMS was networked to a virtual exercise in August 2015, allowing aircrew operating the simulator at No.

285 Squadron's commanding officer, ninety per cent of C-130 flying training was conducted in the FFMS.

[22] In March, a commemorative cairn and garden was unveiled at Richmond in tribute to the squadron's inaugural commanding officer, "Zip" Szypula, who died in March 2001 with his partner and her daughter in an avalanche in the Himalayas, while preparing to climb Mount Everest.