When Russia invaded Ukraine in February, the question most analysts were asking was not whether Russia would win. It was how fast. On almost every quantifiable metric from military strength to economic size Russia has decisive advantages over Ukraine. A swift Russian victory appeared inevitable. Of course, that swift victory didn’t happen. And in recent weeks, the direction of the war has begun to tilt in Ukraine’s direction. On Sept. 6, the Ukrainian military launched a counteroffensive near Kharkiv in northern Ukraine and regained 3,400 square miles of territory in a week — more territory than Russia had captured in the last five months. Analysts are now saying it’s unlikely that Vladimir Putin can accomplish one of his chief aims: annexing the Donbas by force. Andrea Kendall-Taylor is the director of the trans-Atlantic security program at the Center for a New American Security. She’s a former intelligence officer who, from 2015 to 2018, led strategic analysis on Russia at the National Intelligence Council. When we spoke, she was recently back from a trip to Ukraine. And she believes that the long-term trends favor a Ukrainian victory. In this conversation, Kendall-Taylor helps me understand this watershed moment in the war. We discuss why Ukraine’s recent counteroffensive was so significant; how it and other recent developments have hampered Russian morale, manpower and weapons supply; whether sanctions are really influencing Russia’s strategy, and how sanctions might get worse; how this conflict is profoundly changing Europe; whether this recent turn of events signals a possible Ukrainian victory; why “personalist dictators” like Putin can be so dangerous when backed into a corner; how likely it is that we’ll see stalemate or settlement negotiations in the near future; how Kendall-Taylor rates the likelihood of various outcomes; what we should expect in the next phase of the war and more.