I'm changing all the fluids on my 2008 Heritage Softail. I have checked my service manual and the owners manual and can't find out if you check the primary on the jiffy stand or upright. Naturally it would have to be checked cold. It gives the amount (32 oz.) and says not to overfill. Also I can't find out if you check the transmission hot or cold but it says to check the engine oil and transmission on the jiffy stand. Any help is appreciated.

 

Have someone hold the bike vertical and fill the primary until the oil just touches the brass colored metal ring at the bottom of the clutch pack.

My early Dresser (with the smaller primary,) takes 32 oz. Please check again, but I think Softail / Dynas took more like 38 oz.

 

I've used RedLine oils for many years. If you buy their V-Twin PowerPak, it included a snazzy funnel for filling the trans and primary.
http://www.redlineoil.com/Products.aspx?pcid=19