The context of retirement has changed over the last decades, but there is little knowledge on whether the quality of retirement adjustment has changed as well. Changes in retirement regulations and historical differences in resources may affect the quality of adjustment and increase inequalities between different socioeconomic groups. In the present study, we investigated historical differences in retirement adjustment by comparing cross-sectional samples of retirees from 1996, 2002, 2008, and 2014, based on the population-based German Ageing Survey. Adjustment was measured with three different indicators (perceived change in life after retirement, retirement satisfaction, adjustment difficulties). Retirement satisfaction was higher in later samples, but for the other two outcomes, there was no evidence for systematic increases or decreases in levels of retirement adjustment with historical time over the studied period. White-collar workers reported better adjustment than blue-collar workers did, and for two of three outcomes, this effect was stable over time. The white-collar workers’ advantage concerning retirement satisfaction, however, increased. We conclude that in Germany, at least for those who retire within the usual time window, adjustment quality has not changed systematically over the examined 18-year period. We only found mixed evidence for a growing social inequality in the retirement adjustment. However, as individual agency in choosing one’s retirement timing and pathway is increasingly restricted, social inequalities in well-being before retirement may increase.