In 2014 the Russian Federation laid claim on Crimea, causing a change of regime and reportedly profound changes in Internet regulation and connectivity in the peninsula. The goal of this study is to introduce tools to monitor this, and similar situations, and to document changes that happened to the Internet in Crimea. This analysis aims at deconstructing a simplistic vision of a geopolitical controversy, by looking into technical arrangements between providers on the international and regional level, and in the context of international sanctions. We employ a multidisciplinary approach, combining sociological fieldwork with Internet measurements to cross-verify our findings. This paper sheds light on some transformations on Crimean networks through an analysis of AS dependencies and semi-structured in-depth interviews with ISPs from the region. We show that network measurements provide an impartial assessment of the effect of politically relevant changes, and allow us to monitor the impact of geopolitical and legal constraints on the networks, such as international sanctions. We believe this work lowers the barriers for interdisciplinary studies that covers Internet infrastructural changes and sets a first milestone to automate such studies in the future.