We study factorization in single transverse spin asymmetries for dijet production in proton-proton collisions, by considering soft gluon radiation at one-loop order. We show that the associated transverse momentum dependent (TMD) factorization is valid at the leading logarithmic level. At next-to-leading-logarithmic (NLL) accuracy, however, we find that soft gluon radiation generates terms in the single transverse spin dependent cross section that differ from those known for the unpolarized case. As a consequence, these terms cannot be organized in terms of a spin independent soft factor in the factorization formula. We present leading logarithmic predictions for the single transverse spin dijet asymmetry for $pp$ collisions at RHIC, based on quark Sivers functions constrained by semi-inclusive deep inelastic scattering data. We hope that our results will contribute to a better understanding of TMD factorization breaking effects at NLL accuracy and beyond.