Many migrant sending countries have developed engagement policies as a way of facilitating interactions and relationships with their respective diasporas. Ukraine's challenge in developing a policy of engagement is complicated by the diversity of its diaspora. This diversity is conditioned by the political dynamics of the countries in which they have settled permanently and/or reside temporarily, timing and conditions of exit from Ukraine, generational distance from Ukraine, and the length of time a Ukrainian identified community has 'lived in the diaspora'. The paper analyzes how the diversity of the Ukrainian diaspora poses challenges and dilemmas for how the Ukrainian government develops a diaspora policy as the war with Russia grinds on.