I noticed a oil drip that originated from my left rear shock today after I sat on it and fired it up while doing a bit of work. My question is, is the shock shot for sure or do they sometimes leak a bit after a while of non use? Should I replace immediately or just keep and eye on it to see if it keeps leaking?

If it is shot then it sure didnt last long because it only has 7000 miles on it even though it's an '07 (I bought it used late last summer).

 

Where did the oil come from? Bottom near the boot or at the air hose connection? You can pull the boot down and inspect it for oil. If you find oil there, maybe clean it up and take it for a ride. Inspect it again and see if more oil has leaked. If it's a seal, manual says to replace it.

 

It originated from under the boot so I imagine it is a seal.

 

I know some shocks can be rebuilt, but my 09 service manual says "Air shocks are not repairable. Replace if damaged, worn or any sign of leakage is discovered." Might want to call your local shop & see what they say...

 

My right shock did the same thing after only 2,000 miles. Took it down to my dealer and they swapped it out out right then and there. Took a brand new one off of bike they just uncrated when they couldn't locate replacement in a 50 mile radius. Bike was under a year old at the time. Do you have an extended warranty?

 

This company does Harley shock rebuilding when they lower the shocks:

http://bitchinbaggers.com/products/drop-shocks/

I don't know if they rebuild them and leave them stock, but you could always call and ask them. Otherwise its a great time to get that back end slammed.

 

I've also noticed that when I have mine on the jack with wheels hanging that left rear shock is dripping a little from the under the boot. Enough to run down the exhaust and leave a few drops on the floor. Figured it was from leaving it on the jack to long. It doesn't leak sitting on the floor and it holds air as normal as it did before. Have put on about 500 miles on it since I noticed the leak, about half with the wife on back and haven't noticed any ill effects. Got me wondering how much oil is in one. Going to put it back on the jack to see if leaks again.

 

Well, as mentioned the stock shocks are not rebuildable so I guess it's time to replace. I dont think the shock is very bad but the seal must definitely be on it's way out at a paltry 4 years and 7000 miles.
I picked up some Progressive 416's as replacements from Dennis Kirk for $280 shipped. That's only $100 more than a single stock replacement shock from the dealer.

 

Unfortunately those stock shocks are as cheap as chips inside, which is why they don't perform very well, but you have certainly not got your money's worth out of them. There are a lot of shock brands out there to chose from, that range from good enough to superb, depending on how deep your pockets are. After studying HDF threads I went with custom-built Ohlins from HDF sponsor Motorcycle Metal. The bike is transformed! No more cheap air shocks for me. Time for a change I suggest!

 

Mt right one did the same thing. Took it to the dealer and waited while they replaced the shock and tire. Had around 1k on that tire