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The negotiation period that followed the aftermath of the 2016 Brexit referendum was marked by significant political instability in the United Kingdom. In this context, major divisions within the Conservative Party could have created opportunities for Jeremy Corbyn’s Labour Party. However, the strategy of “constructive ambiguity” that Labour adopted was eventually a failure, ending in resounding electoral defeat in 2019. This article analyses the choices made by the party in this context, considering both party elites and grassroots activists, based on qualitative data collected on both of these levels of the organisation. It shows that the leadership’s control over the party was highly dependent on both a precarious coalition of organisational actors and support from the members. Disagreements within the party – including among Corbyn’s supporters – meant that taking a clear stance either for or against a second Brexit referendum could have jeopardised Corbyn’s position. Ambiguity was thus seen as the only way to keep the party united around its leader.