AbstractThis essay reflects on the problematic relationship between informal settlements and built heritage in Metro Manila, Philippines. Trained as a historian with scholarly and middle‐class socio‐civic sensibilities, I am oriented toward the preservation of historically significant structures. Such a seemingly safe positionality, however, is often made problematic by the reality of informal settlers occupying heritage sites, especially in the bustling cities of Asia’s so‐called “developing economies.” This complexity goes beyond finding the right balance between preserving mementos from the past and the material needs of the present. One cannot simply take a stance privileging socioeconomic provision over historical conservation, or vice‐versa, without accounting for class positionality, competing definitions of heritage, state‐capital relations, and the varying degrees and modalities of agency exercised by informal settlers. This paper foregrounds the ongoing struggle of informal settlers in Intramuros, Manila’s centuries‐old, Spanish walled city, by historicizing its “decline” from being a colonial nerve center to an area of blight. At present, these long‐time residents, who also provide the necessary labor for the tourism industry that sustains Intramuros, find it increasingly difficult to maintain their communities, even as tourist arrivals and the revenue they generate keep growing in number. Their situation provides insights that can deepen—and even unsettle—our understanding of this brewing tension between crumbling markers of the past and the present‐day inhumane housing conditions of our cities’ marginalized people.