Small settlements as a category are doing fine in the Netherlands, contrary to overall sentiment. Small settlements do face specific issues, though, issues that one would expect to see in larger cities, possibly the result of the hybrid urban nature of the Netherlands: many small cities in a vast urban region. This article showcases four challenges that small Dutch settlements face, each in a particular way intersecting with built heritage or building vacancy: induced seismicity, the production of synthetic drugs, spilt over mass tourism and the vulnerability of 1970s and 1980s community buildings as young heritage. By addressing these cases, the article seeks to explore the breadth and region-specific nature of actual challenges faced at the crossroads of small settlements and up-and-coming built heritage.