I'm doing the belt and starter on my 1994 Heritage Softail. It has a small leak when warm and shut off which doesn't really surprise me. However after I took the primary cover completely off, I noticed quite a bit of grease and a bolt sticking out that I did not loosen. I'm wondering if it could be the primary case leaking and causing this problem or if it is the engine cases. I'm assuming it is the engine cases but I'd like to check. Also, the starter solenoid is pretty much worn out, so I bought a rebuild kit for it. I'm wondering if you guys just rebuild that when doing this type of job or do you get the whole starter rebuilt? Thanks. Here's a couple pics.

 

I'd say your primary and trans are ok but yea...the main bolt for the cases is definitely your leak...I would replace the nut with a lock nut and maybe even blue loctite all of them (one at a time) and torque to 15-17 lbs.. At least check them all, as for the starter if it is just the solenoid, just replace it. Make sure you check your pinion for damage..

 

Don't forget to remove the old large o-ring,looks like still there in pic.

 

That particular bolt does not have a nut, it threads into the other case...and if it is stripped, things will get ugly in a hurry...good luck

 

True That,
I believe that there are only 2 case bolts with nuts....Hopefully it just backed out....

 

Stripped bolts/threads don't usually walk much cuz they bind up. So I hope for your sake it can be cleaned up and retorqued and maybe blue locktite, check them all.

 

I haven't fully checked anything yet but it looks to have been backed out over time. I'm surprised all it takes is 15-17 ft. lbs. but after reading the service manual a few times it does say that. It doesn't mention anything about using Loctite but I doubt it would hurt. Seems strange that they wouldn't use something to lock it. I think the washer on that bolt is just a flat washer, not a lock washer.

 

That is correct on the washer and only use the Blue Loctite on that bolt..