Finally got the replacement transmission gasket and hoping to put it on this weekend. While I'm in it, I want to go ahead and change the engine oil as well.
The bike is leaking a lot and I've tied it to two places:

1 - the transmission gasket, leaking down the kickstand (previous post)

2 - a screw underneath the engine. Now I'm guessing this is the drainage screw for the sump pump that I've read about in other posts that strips pretty easily.

Am I correct? Is there anyway to shore this leak up? The service manual only describes what level the oil should be at and doesn't explain this screw.

 

It always helps to note the year of your bike in the post.

By transmission gasket do you mean the primary cover gasket?

Can you post a pic of the screw that you suspect of leaking? Depending on which screw it is it may be possible to remove it and re-install with some thread sealant or whatever.

When i had oil leaking along the side stand it was coming from the shifter shaft oil seal. This can be a common leak, especially if there are forward controls on the bike.

 

sorry, its a 75 - left side shift - no forward controls.

And I was wrong - seems like the screw that is leaking is at the rear of the engine - there is another one at the front of the engine that is not leaking

pictures of the two leaks below:

1 - the screw on the bottom rear of the bike

http://www.flickr.com/photos/67696148@N04/6310674335/http://www.flickr.com/photos/67696148@N04/6310674335/ by http://www.flickr.com/people/67696148@N04/, on Flickr

2 - the leak from the transmission

http://www.flickr.com/photos/67696148@N04/6289699172/http://www.flickr.com/photos/67696148@N04/6289699172/ by http://www.flickr.com/people/67696148@N04/, on Flickr

 

what you dont want to do is try to take out those plugs, they are very easy to strip and if you do its a complete teardown! there are holes put in the cases during the machining of the cases the
way i drain the motor is to start it for a few seconds then drain the tank running the motor gets the oil back to the tank, there shouldnt be much oil in the motor just take the cover loose and lean the bike over to drain what little there is

 

Ok, so don't remove the plugs. Now I'm guessing that back plug is for motor oil?

Any suggestions on how to stop the leak?

 

the way your pic looks like the plug isnt leaking, looks like the oil is running down from the primary cover and dripping from the plug, need to clean the whole area up real good and make sure whats leaking, ill bet a primary gasket will take care of your problem, oil runs to the lowest point cant run up hill i can clearly see the primary leaking

 

The drain plug in the second pic is the drain plug for the primary chain case. The oil in there services both the primary and the transmission.

There is no problem removing this plug. Note that it is in an extra thick section of aluminum case so it is unlikely to strip the threads under normal use.

If it should strip it is easy to helicoil it - you just have to remove the primary cover. If it has not already been helicoiled and you are concerned that it might strip someday, then heli it the next time you have the cover off, then you are good forever no worry.

As already mentioned that drip probably comes from higher up. Clean it all up, attach paper towels to suspect places, then either let it sit overnight or ride or both. Then examine the paper towels. It usually takes 2 or 3 runs thru this to isolate the leak[s]. Do not take any fix action until you are certain of the leak location.

The leak in the first pic is not clear to me. You say the bottom rear of the bike. Where is it in the pic? I see a plug with an o-ring? I am not familiar with it is the newer ironheads do not have it.

 

Like others have said..... The rear plug is the transmission drain plug and is meant to be removed to drain the transmission oil.
Your trans plug appears not to be leaking.
If it however, remove the plug which will drain the trans.
Wrap YELLOW Teflon tape around the plug about 4 times and reinstall it.

The same goes for the primary drain plug which appears to have a huge oil drop on it.
More than likely the plug is not leaking gut I believe the leak is coming from the primary gasket and is running down to the low point (the plug) and then falling to the ground.

The plug YOU DO NOT WANT TO TOUCH is the one just forward of the oil pump. LEAVE THIS ALONE, even if it is leaking.
There is no repair should you strip the threads and that is going to happen if you either remove it......... or try to tighten it up.

There is no drain plug for the sump anywhere on the engine.
A Sportster is a dry sump lubrication system with the oil being held inside the oil tank, not inside the engine.
So just remove the oil tank drain plug when you want to change the oil.
pg

 

When all else...well forget about that...just shoot it w/ the shot gun over & over until it has a real reason to leak--that'll teach it, huh?

 

Almost got to the shotgun... but luckily I avoided it!

I changed finshed changing the transmission oil and put on a new primary gasket - now the puppy barely leaks. There is still a SUPER slow drip from the screw on the bottom of the bike, but it's like 1 drop every day so I'm not worried about it.

Didn't do anything to the clutch cable though. The lever gives feels exactly like it did before I took the cover off so I am assuming that I don't need to re-adjust.

However, I tried to start the bike up after it sitting idle for 2 weeks and all I got was the rapid clicking sound. Looking at other threads it looks like this is a battery issue (tested the battery and it's at 11.6V) so I have it setup to charge overnight.

So I am guessing that something is slowly draining the battery? I saw all the circuit breakers when I removed the seat awhile back, so I am guess my next steps are to check those breakers to see if any are hot and then go from there... that sound about right?