ABSTRACT It is common knowledge that the level of landscape heterogeneity may affect the performance of remote sensing based land use/land cover classification. While this issue has been studied in depth for land cover data in general, the specific relationship between the mapping accuracy and morphological characteristics of built-up surfaces has not been analyzed in detail, an urgent need given the recent emergence of a variety of global, fine-resolution settlement datasets. Moreover, previous studies typically rely on aggregated, broad-scale landscape metrics to quantify the morphology of built-up areas, neglecting the fine-grained spatial variation and scale dependency of such metrics. Herein, we aim to fill this knowledge gap by assessing the associations between localized (focal) landscape metrics, derived from binary built-up surfaces and localized data accuracy estimates. We tested our approach for built-up surfaces from the Global Human Settlement Layer (GHSL) for Massachusetts (USA). Specifically, we examined the explanatory power of landscape metrics with respect to both commission and omission errors in the multi-temporal GHS-BUILT R2018A data product. We found that the Landscape Shape Index (LSI) calculated in focal windows exhibits, on average, the highest levels of correlation to focal accuracy measures. These relationships are scale-dependent, and become stronger with increasing level of spatial support. We found that thematic omission error, as measured by Recall, has the strongest relationship to measures of built-up surface morphology across different temporal epochs and spatial resolutions. The results of our regression analysis (R2 > 0.9), estimating accuracy based on landscape metrics, confirmed these findings. Lastly, we tested the generalizability of our findings by regionally stratifying our regression models and applying them to a different version of the GHSL (i.e. the GHS-BUILT-S2) and a different study area. We observed varying levels of model transferability, indicating that the relationship between accuracy and landscape metrics may be sensor-specific, and is heavily localized for most accuracy metrics, but quite generalizable for the Recall measure. This indicates that there is a strong and generalizable association between morphological properties of built-up land and the degree to which it is “undermapped.”