We argued that feelings of anger about the reforms and worries about one’s capability to survive in the job reflect poor adjustment. We theorized about predictors of difficult adjustment based on the resource based dynamic perspective, generally used to study adjustment to retirement. We used a large scale sample survey among 6,800 older workers in the Netherlands, aged 60-65 at time of interview in 2015. Testing our hypotheses revealed that adjustment is more difficult for certain subgroups than for others. Poor health conditions, manual work and long working careers are the strongest predictors of difficult adjustment. This research suggests that the 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, organizations and governments are challenged to design policies that facilitate more flexibility in the workplace and a in the transition into retirement.