This paper investigates eating behaviours and motivations of early career military trainees from two pathways (officer cadets and army recruits) to understand whether, and to what extent, healthful eating behaviours were present, and what motivates eating in general and healthful habits specifically. The study also sought to understand whether groups need strategies that are pathway specific or are transferrable across different trainee populations. Participants were recruited via email to complete an online survey and through in-person invitations to ensure a diverse cross section of trainees (n = 195) and recruits (n = 297). Two-step cluster analysis revealed three distinct segments with education, opportunity and motivation being the most important variables within a wider multivariate segment formation and stepwise linear regression was performed to identify the most optimal model with the least number of predictors for each segment. The ideal model for the uninterested segment contained nine predictors, seven predictors for the Breakfast skippers segment and eight predictors for the Weight conscious segment. This study found that there is room for improvement in the eating habits of military trainees across military training pathways. Eating motivations, and their associations with healthful eating habits, indicate a need for strategies that are broader than instilling or reinforcing health motivations. Strategies that can be implemented to support healthful eating for military trainees include provision of food preparation and cooking skills training, coupled with provision of social support and environments that facilitate healthful eating. Furthermore, three distinct segments were discovered within the trainee population, indicating that strategies for positively changing trainees’ eating behaviours may not need to be pathway specific, rather it may be possible to introduce the same group of segmented strategies across both pathways. Future research directions and limitations are outlined.