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I’m having trouble filling my oil.
I filled overdrive with 1 1/4 pints (20 oz.)
It did not get up to the fill hole
So I put more in.
It still didn’t get up to the fill hole.
I checked my transmission level and it was over filled
So I drained it to stop flowing out
The overdrive still doesn’t come out the fill hole

I can't see any other possibility except you are filling with the transmission hole, as each unit has both a fill and drain hole.

Ok thanks, I did locate both fill holes and drain holes. I will check the level one more time in the overdrive.

I could have sworn there was some discussion awhile back showing there there was some kind of hydraulic connection between the transmission and the over drive. So filling one side will eventually overflow into the otherside. Perhaps the transmission portion doesn't have a rear seal when it's paired with overdrive, as the overdrive would have its own real seal.

No, not really. Oil can probably pass through the bearings but as thick as it is, that’s unlikely to happen. I’ll have to go through the photos from the Henney R11 that I just overhauled but I don’t recall any openings or holes between the two housings.

While both sections have their own level, fluid is circulated between both per this service letter snippet:

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