The study of the Higgs boson properties is one of the most relevant activities in current particle physics. In particular, the Higgs boson couplings to third generation fermions is an important test of the mechanism of mass generation. In spite of their impact on the production and decay properties of the Higgs boson, the values of these couplings are still uncertain and, in models of new physics, they can differ in magnitude as well as in sign with respect to the Standard Model case. In this article, we study the possibility of a wrong sign bottom-quark Yukawa coupling within the framework of the minimal (MSSM) and next-to-minimal (NMSSM) supersymmetric Standard Model. We find that a wrong sign regime is not possible in the MSSM without violating experimental constraints, and we numerically examine the parameter values which give a wrong sign bottom Yukawa within the NMSSM. Possible experimental tests are also discussed, including novel decays of the heavy CP-even and CP-odd Higgs fields that may be probed in the near future and that may lead to an explanation of some intriguing di-boson signatures observed at the ATLAS experiment.