Feminist scholars and activists have for many years pressured policy makers to address gender inequalities in their policy responses. As a result, gender is increasingly being mainstreamed into both humanitarian and development policies carried out by the United Nations as well as other donors. Drawing on field work in Jordan, Lebanon, and Turkey that included interviews with a range of international and national non-governmental organizations (NGOs), as well as staff members from a variety of United Nations organizations, this paper explores the degree to which and how gender has been mainstreamed into the Syria response, with a particular focus on the 'livelihoods' component of the response, which focuses on income generation for refugees. The analysis focuses on the role that both local and global structural factors play in shaping the response, with comparisons being made across the three country contexts, as well as a broader focus on the importance of understanding existing outcomes in the context of neoliberal globalization. A related emphasis will be on challenges associated with the process of implementing a gender mainstreaming agenda in a context that is increasingly being defined as straddling the humanitarian and development divide, in light of the fact that the Syria crisis is nearing almost a decade. Whereas humanitarian approaches tend to be more short term and involve providing for refugees basic needs, because of the protracted nature of the crisis, more emphasis is now being placed on creating employment for example. This paper also will look at challenges that have arisen during this conflict, and how UN entities and donors have adjusted their approach over time with an emphasis on how both NGOs and UN entities have tackled pressures to ‘gender mainstream’ in a political context that is highly fraught.