Beyond conserving urban heritage, the concept of historic urban landscapes (HULs) aims to tackle poverty and inequality, as well as to improve the quality of human settlements, through a people-centered approach in the context of rapid urbanization. This paper demonstrates the adaption of HUL tools and methodologies to investigate a slum in a historical city—the informal settlements along the Mae Kha Canal in Chiang Mai. An on-site field survey of the characteristics of the settlement’s composition and interviews with stakeholders, local authorities, and inhabitants were conducted. The analysis revealed that there is a gap between the desired strategy of the Mae Kha Canal agenda and the actual conditions of the location. The aforementioned contrast is discussed to suggest alternate options for upgrading the informal community while preserving its ancient walls, in line with HUL principles. The conclusion highlights the benefits of introducing the HUL approach in a slum setting and provides recommendations for deteriorated neighborhoods elsewhere that are either surrounded by or adjacent to historical features needing resilience.