This Article highlights the legal and procedural restrictions a Member States faces during its withdrawal from the EU and subsequent talks on a future trade relationship by analyzing the unprecedented case of the UK. One such restriction consists of an obligation to negotiate withdrawal as a result of the principle of sincere cooperation. Other limits derive from the withdrawal process itself, designed as it was by the European institutions on the basis of a very scant Article 50 TEU. By then comparing the three substantive pillars of the EU-UK WA—citizens’ rights, the financial settlement, and the Irish border— with the UK’s initial negotiating red lines, I offer two conclusions: That the aforementioned constraints on the withdrawing state can significantly weaken the defense of its interests during its withdrawal process and that having to agree to important issues in a first and separate stage of “orderly withdrawal” talks also diminishes the state’s bargaining power with regards to the next stage of negotiating a future partnership with the EU.