Attachment to one's former occupation and met expectations regarding retirement were proposed as predictors of the adjustment of military retirees. While results suggested that occupational attachment had a minimal impact, the extent to which expectations of civilian work, financial, and family aspects of life were met emerged as significant predictors of satisfaction and adjustment after military retirement. These findings suggest that the characteristics of the post‐retirement environment, and expectations regarding this environment, outweigh the importance of occupational attachment in determining post‐retirement adjustment in this setting.