This paper presents a synopsis of the challenges and limitations presented by existing and emerging land use/ land cover (LULC) digital data sets when used to analyze the extent, habitat quality, and LULC changes of the monarch (Danaus plexippus) migratory habitat across the United States of America (US) and Mexico. First, the characteristics, state of the knowledge, and issues related to this habitat are presented. Then, the characteristics of the existing and emerging LULC digital data sets with global or cross-border coverage are listed, followed by the data sets that cover only the US or Mexico. Later, we discuss the challenges for determining the extent, habitat quality, and LULC changes in the monarchs’ migratory habitat when using these LULC data sets in conjunction with the current state of the knowledge of the monarchs’ ecology, behavior, and foraging/roosting plants used during their migration. We point to approaches to address some of these challenges, which can be categorized into: (a) LULC data set characteristics and availability; (b) availability of ancillary land management information; (c) ability to construct accurate forage suitability indices for their migration habitat; and (d) level of knowledge of the ecological and behavioral patterns of the monarchs during their journey.