This paper lays out potential options available to the conflict parties involved in the war in Ukraine on the triggers, conditions and modalities for the relaxation of sanctions as part of an eventual peace agreement, and for their reimposition in connection with the verification and monitoring of the implementation of the settlement. It also explores sanctions relief in relation to a possible security guarantee for Ukraine that could be linked to a wider negotiated peace agreement, whereby some sanctions could be reimposed through snap-back provisions in the case of breaches of the peace agreement. In reviewing earlier cases of sanctions easing across a number of jurisdictions, it finds that sanctions relaxation does not form a strategic part of most sanctions planning or execution. Instead, protracted autonomous (or unilateral) sanctions regimes – imposed outside the UN framework – that are reinforced and broadened over time and imposed by a coalition of states and organisations are becoming the norm rather than the exception. At the same time, there is some useful precedent for sanctions suspensions that policymakers can draw on in the Russia context, should the need arise. The United States (US), European Union (EU) and United Nations Security Council (UNSC) have all used sanctions relaxation with some degree of success (albeit often temporary in nature) in recent years. This has taken a wide range of forms and sequences and has been used to fulfil a variety of objectives, including supporting various stages of conflict resolution and peace agreements. Sanctions easing remains unlikely in the Russian context in the immediate future, however, due to the severity of the security threat, lack of political will and absence of trust. This article concludes that sanctions flexibility could nevertheless play a central role in all phases of an eventual peace agreement as well as in relation to a security guarantee for Ukraine, while outlining a number of key challenges and considerations surrounding implementation and coordination across relevant actors. Factors such as timing, duration, coordination, communications, sequencing, reversibility, scope and strategic combination with other policy processes are all factors that will play an important role at such a point.