Forests that encompass the border triangle of Poland, the Czech Republic and Slovakia currently suffer from centuries of inadequate forest management strategies, including overexploitation during the countries’ respective communist regimes and high stress levels due to airborne emissions from heavy industry. Since the fall of the Iron Curtain, each country has approached forest monitoring, protection and the improvement of forest conditions in its own way. Spaceborne remote sensing of forest changes across country borders offers great potential for better understanding the underlying drivers of change and for developing comparable indicators between countries. For this paper we evaluated how forests changed in the border region of Poland, the Czech Republic and Slovakia between 1987 and 2005 and how these changes depended on industrial transformations before and after 1989. We used Landsat Thematic Mapper imagery and a Support Vector Machine (SVM) classifier to assess forest cover change between 1987 and 2005. Our results showed that 8.12% of the forest stands in our study region were degraded either partially or completely during that time period, a percentage that equals 14,972 ha of the area’s total forest cover. At the same time, 7.57% (13,951 ha) of the area were reforested or regenerated on previously damaged forest stands. Forest changes were similar in the Czech Republic and Slovakia, but differed in Poland. Comparing forest composition, topography, and aspect with forest decline revealed the importance of forest management and pollution legacies from communist times when explaining today’s forest disturbance patterns.