Political upheaval in the Middle East and North Africa caused by the Arab Awakening provided a new impetus to studying ‘fragile states’ problematique which came to the forefront in political and expert discourse in the last decade. Examining international engagement in fragile states and situations through the lens of risk-management seems to be especially relevant. This paper unveils key dilemmas faced by external actors in aiding fragile states and choosing the following parameters of engagement: aid volumes, duration of engagement, aid channels, financial instruments, procurement modalities, implementing partner in recipient country, conditionality and priority sectors. Each of correspondent eight sections starts with positing hypotheses about donors’ choices and proceeds with their verification based on empirical data. The paper concludes with observations on potential and limitations of a selected analytical lens and on ways how to improve its utility. First, no option seems to allow external actors to simultaneously mitigate contextual, programmatic and reputational risks and maximize political and economic dividends, and donors tend to prioritize egoistic interests over mitigation of any other risk factors. Second, multiple counterexamples to each hypothesis derive from heterogeneity of both ‘fragile states’, which vary dramatically in terms of determinants, manifestations and consequences of their fragility, and community of donors, which often assess risks of engaging with the same partner countries differently given their specific long-term national interests, aid management systems, imperatives of reacting to shifts in domestic political and economic environment or other factors. Third, to better navigate a logical labyrinth and reconstruct an objective picture of interactions of these two groups one should meet at least three conditions: 1) taking into account the emergence of non-Western donors and its impact on the established donors’ strategic considerations; 2) collecting detailed data on emerging donors’ engagement with fragile states as well as on volumes and composition of military and non-ODA security assistance provided to fragile states; 3) studying the partner countries’ perceptions of risks related to receiving external assistance.