I’d try to take some pictures for you but I’m not at the shop today. On the passenger side of the tail housing you can easily see the filler plug (with the square head for a removal by a wrench). To the right of that, and down low near the casting for the motor mount, is the drain plug. It’s smaller than the filler plug and has a female hex opening for an allen wrench. Often its socket is full of old grease and road dirt, so you’ll have to use a pick to clean that stuff out. I forget the hex size….maybe 1/4”. Don’t try to get a 90 degree allen wrench in there. We use a short allen that is made with an adapter for a 3/8” socket drive. You have to attack it straight on. This is normally adequate to loosen and remove the plug. Once in a while we’ll find that the plug is rusted in place and the allen wrench will strip out the hex socket of the plug.
It’s a pain in the rear end to get it out now so you can choose to leave it in place or end up pulling the extension housing off the transmission and using heat or drilling it out etc. The oil sump in the overdrive section is common with the front section and will drain out through there as well…..just not as completely or quickly as it would through its own plug.
If you are successful in removing the plug, it should allow the gear oil to flow. If nothing comes out, try poking a pick tool in the opening in case some internal debris is blocking the drain. If nothing comes out, I’d be very concerned that the overdrive gearing has been running dry and may be damaged.