This article discusses the inherent limitations of law in transitional justice processes regarding land grievances. Through analysis of the case of Timor-Leste (East Timor), a country marked by post-colonialism, post-authoritarianism, and post-conflict. The article shows how complex transitional justice regarding land grievances can be, and argues that a legalist perspective gives a limited view of these grievances, both for studying and finding solutions to them. The article employs the concept of ‘wicked problems’ to overcome the limitations of law. First, it shows how these grievances should be studied through a multi-disciplinary approach instead of a purely legal one. Second, it argues that transitional justice regarding land grievances is primarily a political issue, and creating adequate arenas for political negotiation should be prioritized. Finally, the article shows that, due to its complexity and political nature, transitional justice for land grievances is ultimately a search for acceptable, rather than optimal, solutions.