Russia’s attack on Ukraine in February 2022 has not only brought war back to the European continent, it has also created a new urgency for the European Union to allow new members to find economic and strategic protection within its confines. While no accession procedure has been successfully concluded since 2013, the list of candidates is growing. In June 2022, the European Council decided to grant the status of candidate country to both Ukraine and the Republic of Moldova. This was greeted with great enthusiasm, in particular in Ukraine—which now expects a swift accession in reward for the enormous price it has had to pay for its European choice.The key question this chapter addresses is which dynamics have evolved in this early accession process under the conditions of war, where the EU strives to defend the rule of law and democracy internally and externally simultaneously (in particular because of past experiences of how vulnerable democratic achievements are to recession), while at the same time trying to prove its geopolitical capacities by providing credible accession perspectives. The literature on EU conditionality provides us with helpful insights into factors conducive to the transformation of a candidate country along EU conditions (e.g. clarity, tangibility of rewards, absence of veto-players). This seems to make Ukraine an ideal candidate for successful transformation, as the renewed emphasis of the ‘geopolitical’ EU on enlargement strengthens the credibility of the promise, and a renewed enlargement methodology contributes to clarity and increases (tangible) rewards along the way. Additionally, an active Ukrainian civil society is putting pressure on political elites to continue on their European path. The close linkage of EU accession with reconstruction plans for Ukraine also makes successful EU integration an effective remedy for domestic challenges.We argue, however, that in order to comprehensively understand ‘membership politics’ and the politicisation of EU conditions, it is essential to address the contextual interpretation of the norms posed by the EU as part of its accession conditionality. For this, we combine the concept of conditionality with approaches to norm contestation from International Relations (IR) Research. This induces a shift of perspective from a unidirectional norm-giver/norm-taker perspective, closely assigned to conditionality approaches, towards a focus on the web of interactions between actors on the EU and the Ukrainian side as they engage with, interpret and enact norms based on their social context. By example of the reform of the Ukrainian judiciary (and here in particular the Constitutional Court of Ukraine) we show how the ‘sovereignty argument’ is put forward to challenge the “West’s right to evaluate”. Furthermore, the contestation of time frames is of high salience not only because Ukraine demands a ‘fast track accession’ against the will of some EU Member States, but also because it raises the stakes as to how ‘sufficient progress’ for gaining promised rewards is assessed. It is thus indispensable to conceptualise and address contestation in order to understand the current challenges of turning Ukraine’s candidate status into a meaningful membership perspective under increased geopolitical pressure, and while a war is raging on the EU’s doorstep.