Despite working life prolongation having been at the center of the policy agenda in Europe for the last two decades, organizations’ engagement in formal age-management activities intended to strengthen older workers’ motivation and work ability appears limited. Given policies to extend working lives, negotiated individualized work arrangements—often called idiosyncratic deals (I-deals)—can be an informal and complementary approach to formalized age-management practices, improving the person–job fit and helping older workers extend their working lives. Nevertheless, research on I-deals and retirement preferences remains scarce in the Nordic context, where collective agreements regulate conditions of employment and the employer–employee relationship. Using confirmatory factor analysis and structural equation modeling, this study examines five areas of I-deals (i.e., Task and Work Responsibilities, Workload Reduction, Schedule Flexibility, Location Flexibility, and Financial Incentives) and their relationships with retirement preferences among Swedish public-sector employees aged 55 years or older (n = 4,499). Findings show that I-deals are generally less prevalent among women and older employees, as well as among those with poor health, in lower socioeconomic positions, and with shorter organizational tenure. Regarding retirement preferences, we found Task and Work Responsibilities to be related to later preferred retirement age, while, surprisingly, the opposite was observed for Workload Reduction, probably because individuals who received workload reductions also reported poorer health. Comparatively, factors such as matching employees’ competence, experience, and growth opportunities seem to be the most important for public-sector employees’ retirement preferences.