All over the world the retirement landscape is changing. Probably one of the bigger and more fundamental changes is the rise in the pension eligibility age. The fact that these reforms came quickly after the closing of early retirement opportunities urged the pre-pension cohorts to adjust their retirement outlooks. This research studied older workers’ emotional reactions to reforms that induce them to extend their working lives with a number of years. Using data from a large scale sample survey among 6,800 older workers in the Netherlands, aged 60–65 at time of interview in 2015, we examined why the pension reforms trigger stronger emotional reactions in some individuals than in others. We integrated theoretical insights from the theory of emotion and the resource-based perspective on retirement adjustment. Testing our hypotheses revealed that emotions are stronger among individuals that have less access to resources. Anger and worry is more prevalent among older workers in more demanding jobs, with less favorable personal (health, wealth) and social resources (no partner support). This research suggests that policy makers—mostly higher level professionals who are much less exposed to the challenges of working longer—have underestimated the psychological and social impact of the reforms on vulnerable groups of older workers and, in particular, less educated older workers with lower social status. With a further increase of retirement age to be expected, policy makers are challenged to design policies that spare vulnerable groups in particular, for example, by facilitating more flexibility in the retirement transition.