The Lamu Port-South Sudan-Ethiopia Transport (LAPSSET) corridor project is intended to traverse northern counties of Kenya, link with other corridors in Africa and attract investors. This article explores the dynamics of anticipation and how they relate to contestation over land, compensation and the benefits of development along the corridor area, finding that a variety of actors have different visions and capacities to position themselves favourably to achieve economic benefits from the corridor. Anticipatory behaviours may be both private and collective, the latter consisting of group claims on land prompted by the desire to block private actors, and also to prevent economic or political dominance by other ethnic groups. Thus both private and collective anticipation may exacerbate inequalities and lead to conflict along lines of ethnicity and class. Further, conflict may be ignited in an opportunistic manner to remove other potential beneficiaries, which is itself an example of anticipation.