I'll assume you're talking about regular gear oil like 90W or something like it. What kind of tractor? Makes a difference in what you have to do to get in and get out the sludge, and whether it's economical to use my method.
What I've done was drain her and then take the cover and shifter off in a way that I have a prayer of getting it back on right. Borrowed mother's measuring cups and scooped out all the hard sludge I could reach. Put mother's measuring cups in the dishwasher by themselves with a double-charge of soap and started it. Then took a parts brush and kerosene and swabbed down everything in sight (in the tranny, not the dishwasher!). Don't spare the kerosene in this part of the process. Then I pour some clean kerosene over everything and let it run out.
Final steps in my program are to put the cover and shifter back, refill with half-kerosene/half gear oil and take her out for a spin, using all gears and the PTO running.
Try to warm it up. If you're still with me, take her to the post office to get the mail or out to the store and have a coffee with the boys. When you get home, drain it once more and refill with the recommended lube.
That works for an open-top tranny like on a Farmall B pretty well. If you have a large capacity tranny or one that means removing a top deck to open it up (like my SuperC) but you're unwillinhg or not set up to remove the top, I'd still suggest going at it in the same general way. It may mean digging out what sludge you can with a loop of wire through the drain hole, but you should still try to rinse things off with kerosene. Instead of a run to town, you could put the rear up on stands and run it with a full charge of kerosene for a few minutes, and then drain before refilling.
The latter is a little less effective, and may require checking the condition of the tranny lube (never a bad idea in any case) next year, and changing it out again if you still have excess crud or moisture floating around.
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