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Under what circumstances does foreign donor assistance during war-to-peace transitions contribute to the strengthening of civil society and the deepening of democracy? I answer this question through a comparative study of civil society development in the Palestinian territories and El Salvador, where I conducted 130 interviews with directors of donor agencies, grassroots activists, and directors of NGOs. Divergent civil society developments in the Palestinian territories and El Salvador after the signing of peace accords in the early 1990s present a real puzzle given the pre-accord similarities in civil society organization between the two cases. Both the Palestinian territories and El Salvador had a legacy of rich, vibrant grassroots organization and civil society activity during their protracted conflicts. In both settings, grassroots organizations have played central roles in non-violent resistance, consciousness-raising, and the provision of community services. Moreover, after the initiation of the peace processes in both the Palestinian territories and El Salvador, foreign donors provided substantial assistance to civil society groups. However, their civil society developmental paths diverged sharply during the war-to-peace transition. In the Palestinian territories, existing civil society organizations have engaged less actively with their previous grassroots constituencies since the start of the war-to-peace transition, and the number of grassroots-based civil society organizations has decreased. Moreover, many of these organizations have been limited in their access to institutions that engage the state. In El Salvador, the re-constitution of civil society has led to its broad access to institutions that engage the state and to higher levels of grassroots inclusion in the political transformation process. / I argue that these divergent outcomes in the Palestinian territories and El Salvador reflect the differential effects that foreign assistance has on civil society after more or less inclusive political settlements. I find that in cases like the Palestinian territories, where the political settlement excludes important socio-political groups, foreign donor assistance is less likely to contribute to the strengthening of civil society or the deepening of democracy. Rather, foreign donor assistance to civil society is more likely to exacerbate political polarization and weaken civil society by further privileging those select groups already favored by the terms of the non-inclusive settlement. Conversely, after more inclusive political settlements like in El Salvador, foreign donor assistance can play a more constructive role in developing civil society and contributing to the deepening of democracy by encouraging grassroots organization, and expanding access to political institutions that engage the state.