The 44-day Karabakh War reshaped the geopolitical landscape of the South Caucasus region. Azerbaijan regained its territories and historic justice was restored. What is transpiring in the region at the moment will decide its future for many decades to come. Peace, prosperity, and inclusive development in the long-fragmented South Caucasus region may take shape through normalization of relations and proper communication between Armenia and Azerbaijan. The two nations of the region paid a very high price in the name of the occupational, expansionist, and irredentist policy of Armenia that disregarded international law and attempted to perpetuate the ‘results’ of the illegal occupation of the territories of Azerbaijan. In the context of the new reality, there are several important areas that demand a good deal of work and resource mobilization on the part of Azerbaijan, as well as bona fide cooperation on the part of Armenia. Issues in the political track, i.e., those related to the Armenia–Azerbaijan normalization process and the signing of a peace treaty, demilitarization and demining, reconstruction of the liberated territories, connectivity, and humanitarian issues, are currently the most pressing ones and require cooperation, dedication, and continuity. This piece attempts to highlight current work in these areas and define the challenges remaining ahead.