As cities aim for more sustainable patterns of urbanization, intensification has emerged as a core planning strategy. In 2013, the City of Regina set new intensification targets: absorb 30% of annual population growth through intensification and add 10,000 residents to the city centre by 2035. In the decade since, implementation has been unsuccessful. This study explores the barriers to core area intensification in Regina by engaging with key informants through semi‐structured interviews. Our findings identify the most significant barriers as soft market demand, a city centre that is unappealing as a residential context, insufficient political will, an absence of developers who specialize in core area intensification, and unfavourable development economics. These findings illustrate the unique challenges faced by mid‐size Canadian cites in disrupting entrenched development patterns and driving development towards the downtown.