There is limited investigation of how military personnel evaluate their deployment experiences. An understanding of their perceptions would help unit psychologists to advise commanders on ways to improve the deployment experience (and therefore mental well-being) of personnel. This study examined the interplay between deployment overall ratings, personnel characteristics and positive and negative deployment experiences in aid of such understanding. The participants were 1,226 Australian Defence Force personnel who deployed to East Timor and (through a survey) provided an overall rating of their deployment and comments on major positive and negative deployment experiences. Descriptive statistics detail ratings by personnel characteristics, and a hybrid content/thematic analysis details the positive and negative experiences. The study was approved by an Institutional Review Board. Over 80% of the participants rated their overall East Timor deployment experience as positive, with 13% rating it as neutral and 7% as negative. Intrinsic rewards (eg, ability to use skills) were the most commonly expressed major positive experiences of the deployment, with deployment administration and military leadership the most common negatives. Most intrinsic rewards were reported more often in participants with a positive deployment rating, while poor leadership was most frequent in those with a negative rating. Military leadership is corroborated as a negative experience of military deployment, while a new finding indicates that intrinsic rewards are a common feature in positive evaluations of deployment. Leadership is a factor that Defence Forces can address to improve the deployment experience. The study strength is the range and size of the sample, with a limitation the potential for recall bias (the data were collected, on average, 5 years postdeployment). Future research should replicate this type of analysis to build a picture of the experiences and evaluations of personnel from a range of different deployments.