The Obama and Trump administrations have shared the same basic objectives towards Iran but have chosen radically different approaches to that end. While Obama was hailed – not least in Europe – for his emphasis on dialogue and negotiations, his policies still failed to contain Iran’s missile program and its use of “proxies” in other countries. The Trump administration’s emphasis on “maximum (economic) pressure”, in turn, is not per se doomed to failure. The major flaw of Trump’s approach, however, is that it is void of diplomacy. As long as the policy does not include a clearer understanding of the demands of as well as political/financial incentives towards Iran, “maximum pressure” runs the risk of dragging the United States still deeper into the Middle East’s violent conflicts.