This article aims to present and discuss a set of technical matters affecting the maintenance and sustainment cost of military transport aircraft (airlifters). An overview of the military aviation technical support system is provided, in conjunction with a high level discussion on the life cycle cost. Four technical support pillars are defined as part of this analysis: supply, restoration and upgrade, engineering and regulatory compliance. A focused discussion on airlift sustainment factors, based on past experience, is used to identify technical considerations that can be used for the evaluation of new aircraft. A number of technical considerations which are key for cost purposes are identified and mapped against the defined technical support pillars, related to engineering and technical support and airworthiness management aspects. Important practical technical considerations are identified, discussed and critiqued under an independent lens. This article can stimulate discussion of the maintenance and sustainment costs of airlifters, both within military aviation operators and the defence industry community but also within the civil aircraft maintenance industry.