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Key aspects of international policy, such as those pertaining to migration and trade, manifest in the physical world at international political borders; for this reason, borders are of interest to political science studying the impacts and implications of these policies. While some prior efforts have worked to characterize features of borders us- ing trained human coders and crowdsourcing, these are limited in scale by the need for manual annotations. In this paper, we present a new task, dataset, and baseline approaches for estimating the legibility of international political borders automatically and on a global scale. Our contributions are to (1) define the border legibility estimation task; (2) collect a dataset of overhead (aerial) imagery for the entire world’s international borders, (3) propose several classical and deep-learning-based approaches to establish a baseline for the task, and (4) evaluate our algorithms against a validation dataset of crowdsourced legibility com- parisons. Our results on this challenging task confirm that while low-level features can often explain border legibility, mid- and high-level features are also important. Finally, we show preliminary results of a global analysis of legibility, confirming some of the political and geographic influences of legibility.