In German cities, higher levels of education increase people’s propensity to cycle. However, it remains unknown whether this effect is restricted to certain contexts, such as cities with low or medium cycling rates, or whether it is a more universal occurrence. This paper develops and tests competing hypotheses on how the effect of education on cycling might depend on the overall cycling level: (a) educational inequalities in cycling could increase proportionally with the overall cycling level or (b) such inequalities might diminish in high-cycling cities because their advanced pro-cycling mobility cultures encourage cycling among all social groups. I analyse about 150,000 trips made by about 50,000 residents from 143 cities in the Netherlands and Germany using multilevel regression models. Results fall in between the competing hypotheses, meaning that the effect of education is similarly large in cities with low, medium, or high overall levels of cycling. Hence, there is no automatism in the sense that higher cycling shares in general will also imply greater cycling equity.