In this chapter, I build a case for characterising the problems people face in family life as “messy”, bringing Ney's (2009) descriptor for macro-level policy problems into the micro-level system of family interactions. I propose the suitability of this messy characterisation in relation to analyses of real-life problems as “wicked” and “ill-structured”. I point to four markers of messy problems, identifying them as complex, value-laden, conflict-prone, and uncertain, and relate these markers to examples of problems involved in the giving and receiving of family inheritances. I suggest how problem solvers may cut through the messiness of inheritance problems by recognising ambiguous perspectives and values in themselves and other family stakeholders, and by identifying inheritance problems and pursuing solutions as inherently messy but not always unsolvable. I also discuss the role of community education programs in assisting problem solvers to address the dimensions and consequences of messy problem solving.