Well, I installed a tach in my truck and it confirmed my suspicions. My overdrive isn't engaging. It does go into the "free wheeling" mode, but the RPMs don't drop at all.
It is a 55 2nd with the 3 speed column shift. After reading the shop manual, it appears to me the likely cause in either the soleniod, the relay, or the governor switch.
I am about to start down the trouble shooting of the electircal components as outlined in the manual.
Does anyone have some insight regarding what is the most likely cause, or something I am not seeing?