In a large class of models for Weakly Interacting Massive Particles (WIMPs),the WIMP mass $M$ lies far above the weak scale $m_W$. This work identifiesuniversal Sudakov-type logarithms $\sim \alpha \log^2 (2\,M/m_W)$ that spoilthe naive convergence of perturbation theory for annihilation processes. Aneffective field theory (EFT) framework is presented, allowing the systematicresummation of these logarithms. Another impact of the large separation ofscales is that a long-distance wave-function distortion from electroweak bosonexchange leads to observable modifications of the cross section. Carefulaccounting of momentum regions in the EFT allows the rigorously disentanglementof this so-called Sommerfeld enhancement from the short distance hardannihilation process. The WIMP is modeled as a heavy-particle field, while thelight, energetic, final-state electroweak gauge bosons are treated as soft andcollinear fields. Hard matching coefficients are computed at renormalizationscale $\mu \sim 2\,M$, then evolved down to $\mu \sim m_W$, where electroweaksymmetry breaking is incorporated and the matching onto the relevant quantummechanical Hamiltonian is performed. The example of an $SU(2)_W$ triplet scalardark matter candidate annihilating to line photons is used for concreteness,allowing the numerical exploration of the impact of next-to-leading ordercorrections and log resummation. For $M \simeq 3$ TeV, the resummed Sommerfeldenhanced cross section is reduced by a factor of $\sim 3$ with respect to thetree-level fixed order result.