Population ageing poses growing challenges to social security systems, in particular to public pension funds. The study analyses how Working Life Expectancy (WLE) and Healthy Working Life Expectancy (HWLE) in terms of three health indicators developed in Germany. Based on the German Socio-Economic Panel (GSOEP) from 2002 to 2018 (n = 211,141), time trends in labour force rates, mental and physical Health-Related Quality of Life (HRQoL), self-rated health (SRH) and the respective combinations (health indicator*labour force) were analysed for all respondents aged 18–74. WLE and HWLE were calculated using the Sullivan method. WLE and HWLE in men and women at age 18 and 50 clearly increased over time. These increases in HWLE were found in terms of all three health indicators. This development was mainly driven by the clear increase of the labour force rates, since the shares of individuals with good and satisfactory SRH or average and good HRQoL remained largely stable over time. The results show that from a health perspective there have been potentials for increases in WLE during the past two decades and that increasingly more healthy life years are spent economically active. However, life years in the labour force but in poor health have increased, too. The absence of clear improvements in health emphasises the importance of current and future preventive measures to maintain health, especially among the middle-aged and older labour force.