During the week of October 14–20, 2014, Eurasia Daily Monitor presented a series of special issues featuring net assessments of developments across Eurasia since the beginning of the year. Following Ukraine’s Revolution of Dignity on the Maidan, and Russia’s ensuing cynical attack on the country and annexation of Crimea, the reverberations of these events have been felt far and wide across the post-Soviet space. Making sense of what has happened in the past ten months compelled Jamestown to take a step back and place the year’s events into a broader strategic context. The end result of our effort has been to commission a series of political landscape pieces by EDM contributors, which assess developments in Eurasia since the start of the year and anticipate where those regional trends may lead. The following compilation includes all the resulting articles published in EDM in mid-October 2014, as well as three other pieces, which had not been released until now. We hope that this collection can help to outline how the conflict over Ukraine has and is changing the security environment throughout Europe and Eurasia.