The future of Ukraine depends on its relations with the EU. What is the law governing accessions? What are the main challenges facing Ukraine on the path towards EU membership? Going through the pre-accession scrutiny in times of war, Ukraine sets a unique precedent, where more experimentation could be possible to mitigate a huge risk that the EU repeats and amplifies the same mistakes it made in the Western Balkan countries – making the region a hostage of its contradictory and lethargic politics for too long. The evolution of EU enlargement law and the legal-political framework surrounding accessions across the different rounds of EU enlargement demonstrates that EU law is flexible while the practice of its application is volatile and deeply political. Enlargement practice shows that applying pre-accession conditionality may cause significant delays, while not delivering the results expected of it. A new approach to regulating accessions to the EU needs to be tested out before it is too late. This approach should build on Article 49 TEU and seek at least some depoliticisation of the enlargement process to guarantee the rule of law without dubious pre-accession techniques. Such an approach would speed-up accessions while making EU enlargement more predictable, serving the interests of Ukraine and other partners.