The politics of representation has become increasingly complex in recent years. Amid weakening traditional political cleavages, the emergence of new political divides and mounting anti-elitism that have helped the rise of radical populist parties, voters face significant cross-pressures when casting their ballots. Despite a wealth of studies on the role of issue preferences in voting behavior, there are still many unknowns when it comes to understanding how voters trade off competing issue preferences against each other. Studying issue trade-offs is also important against the backdrop of the well-documented preference of radical left and right voters for redistribution and restrictive immigration policies, respectively. To investigate the strength of issue preferences among radical left, radical right and mainstream party voters and the willingness to compromise on their most important issues, we conducted a conjoint survey experiment with 2,000 participants in France, Germany, Italy and Spain. The voting scenario in the experiment featured proposals on salient political issues and different (non)populist stances on political representation. The results from the cross-country study as well as a large replication study with a sample of 4,000 German respondents show that voters of radical right parties are willing to accept large trade offs regarding their other issue preferences as long as their preference for restrictive immigration policies is fulfilled. Differently, radical left, Green and mainstream party voters have a more variegated range of issue preferences, some of them so strong that they are not traded off for their preferred redistribution and EU integration positions, respectively. The findings shed light on trade-offs related to emerging issues such as climate change and the distinct logics behind support for radical parties. They also have implications for the electoral prospects of mainstream and radical parties when trying to reposition themselves in the diversifying issue space of contemporary democracies. As such, understanding how voters navigate issue cross-pressures helps to explain the broader dynamics that are (re)configuring political conflict and voting behavior in Europe.