The present research examines the effects of contract breach on retirement satisfaction. We specifically tested the moderating role of retirement self-efficacy and the mediating role that negative affect may play in influencing the relationships between contract breach and retirement satisfaction, either anticipated or actual. Two empirical studies have been conducted by self-reported questionnaires, with older workers of Spanish descent from Spain—one sample being comprised of workers still in the workforce (Study 1; N = 160) and the other being comprised of recent retirees (Study 2; N = 215). We found that contract breach was positively related to negative affect and negatively related to both anticipated (Study 1) and actual retirement satisfaction (Study 2). Moreover, moderation analyses showed that these effects are strong for participants with low rather than high retirement self-efficacy. Theoretical and practical implications are discussed.