I bought my first bike in the spring of last year. a beautiful 2000 Heritage Softail. Runs excellent. Then one day I checked my oil, now my dip stick shoots out every once in a while., but thats not the issue. When it started shooting out I noticed I was dripping oil and my engine light eventually came on and I got a code. Winter was coming and I was planning to park my bike for the winter anyway, so I haven't started it again since, until yesterday
It fired right away, and I added some oil, because I lost oil due to the dip stick flying out. Now I'm not sure what the oil level should read on the dip stick. I understand my bike needs to be warm when I check it, but my dip stick doesn't have any writing on it. It just has 2 marks. So my question is where should the oil read? In between the 2 lines?

 

It's something blocked in the breather system
making the oil cap blow out.
Always check oil with the engine hot
these things wet sump like crazy. It'll show 1 qt
low cold. 2nd line = full (nearest the cap)

 

Most people fill it half way between those lines... in some engines, it reduces the amount of oil coming out the breathers into the air cleaner.....


Did you add oil before it popped out your dipstick?

I ask because on the softails, if left unstarted for an extended period of time, oil will seep from the oil tank, through the oil pump, and into the sump. If you check your engine cold, notice it's low, and fill it to between the lines..... when you start the engine, within a few minutes the engine will clear the sump, put all the oil back into the oil tank, which now has no room because you added more oil.... and you'll have a mini volcanic oil eruption from your oil tank. Don't ask me how I know....

If your bike has the proper level of oil and it's popping the dipstick out of the oil tank, it appears you have a problem.......

As mentioned, could be breather valves in the heads are malfunctioning, causing crankcase pressure to vent through the oil tank.... Have you done any work to the heads/rocker arms and removed/replaced the breather valves?