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The record of Western security force assistance shows that it often fails to build military capacity. To understand why, we must first examine when states deploy advisors. I argue that states send advisors to weak militaries with the expectation that they will lead to meaningful changes in the local military’s approach to issues like military reform, human rights, civil-military relations, and the foreign policy priorities of the sending state. Advisors use their local embeddedness to build personal relationships with their counterparts that generate influence over the local military at the individual level. I evaluate the theory using a case study of US, UK, Canadian, and Polish support to Ukraine (2014 – 2022). I show that despite Ukraine’s overall interest alignment with its international supporters, reforms at the strategic level were slow and often not implemented. Advisors were limited in their influence over their counterparts because they were not embedded with them. They did succeed, however, in increasing human capital in the Ukrainian military through training. In sum, Ukraine shows the mechanisms of influence during conflict, the importance of personal relationships developed through people on the ground, but also the limits of influence in areas of interest misalignment between supporter and partner.