As mobile and multi-homed devices are becoming ubiquitous, the need for a dynamic, yet secure communication protocol is unavoidable. The Host Identity Protocol (HIP) was constructed to meet this requirement; to provide significantly more secure mobility and multi-homing capabilities. HIP opportunistic mode, which is to be used when other, more trusted mechanisms are lacking, is based on a leap of faith (LoF) paradigm. In this paper, we analyze different Man in the middle (MiTM) attacks which might occur under this LoF, and propose a set of tweaks for hardening opportunistic HIP (HOH) that strengthen opportunistic modes security.