The dilemma faced by Germany in formulating its Afghanistan strategy amidst the Taliban’s return to power and their oppressive policies towards women and minorities is explored by presenting two opposing ration- ales for German involvement in Afghanistan. On the one hand, a certain degree of engagement and dialogue with the Taliban could prevent further escalation by upholding political leverage and making the Taliban more predictive. On the other hand, engaging in dialogue with the Taliban risks compromising Germany’s commitment to its Feminist Development Policy as well as legitimising the Taliban’s Islamist and oppressive rule. Diplomatic engagement and support for Afghan-led peace processes are presented as alternatives. The discussion leads to three broader policy pathways for Germany, among which the resumption of bilateral and the strengthening of multilateral Development Cooperation (DC) with a strict conditionality on women’s rights improvements is considered the most reasonable. With a strict non-legitimisation approach towards the Taliban regime at its core, this pathway calls for a joint EU positioning, continuous negotiations and a broad readjustment of DC funds towards low-risk-high-payoff sectors.