My 1998 FLHTCUI with around 60,000 miles on it....the transmission leak has returned!
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All the seals on the shaft behind the belt pulley were replaced....and it still leaks. Not as bad as it did....but is leaking. I suspect that it will probably get worse.
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What is going wrong here? Apparently, the seals only work for a short time and they fail!

 

When you remove the pulley, there is a spacer that slides on the shaft and through the seal. You need to replace the seal and the spacer. You will see a tiny groove in the spacer, it should not be there, the spacer is worn. A new seal will not make a seal on that groove but will be worn out quickly because of the rough surface on the worn spacer. I'm pretty sure that is the problem.
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Good Luck!
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Dajavu is correct and also watch the belt tension.

 

It is the oil seal behind the primary bearing race on the shaft. Need a puller to get the race off and reinstalled.

 

The spacer was not replaced though....as it was stuck. We were unable to remove it and figured it was probably not leaking there. The spacer should have just come right off, but it didn't.
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The belt tension may perhaps be just a little on the tight side though. However, how would a belt just a little on the tight side make it leak? I've never had this leak with other Harleys I've owned in the past. I will loosen the belt, but doubt that this will cure the problem.
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Any ideas about the stuck spacer?

 

Heat........My Harley Parts guy told me if the spacer wouldn't come off try heating it up. When I replaced my seals, my spacer slide right out in my hands. I replaced my spacer as there were marks that you could barely feel but they were there. Now this is the second time I tore into mine. Mine still leaked and thats when I was told about the oil seal behind the primary bearing race. Replaced that and no more leaks, well not for now......my bike is a 93 Fatboy with 35,000 miles on it

 

Yea, I applied heat to it.....but with no luck though.&nbsp\\;Several of us tried to get it off....just no luck!