95 Dyna. Bought used with 5,000 miles on it. Only 7,400 miles on the mill now.
It's only happened twice, with a warm engine.
But I hit the starter button and get a grinding or clacking type noise. Hit the starter button again, she fires right up.
Anyone know what might cause this ?

 

I’ve got a 95 Dyna and mine has done it a couple times too.
I also had an 09 Road King that did it and it turned out to be the compensator was shot.

 

The OP`s compensator is completely different from an `09.

@KentuckyChristian The description makes me suspect the starter clutch is on its way out.

Make sure the battery and charging system are in good working condition.

 

I figured it was something in the starter.
Battery and charging system are good ( so far). Looks like I'll be putting a starter motor on this winter.

 

A weak battery can reveal a bad starter clutch.

Any work done to engine, like raising compression?

 

Are there any mods to the motor?

 

You don`t need to replace the starter motor, just replace the starter drive clutch.

Item 21 in the illustration, still available from the dealer.

You can get them from the aftermarket, but all you will get is the clutch unit (item 37), nothing else.

illustration

 

Battery and charging system are good.
No mods to engine other than exhaust and air cleaner / breather.
Idle mixture jet has been uncapped and dialed in.

 

Battery and charging system are good.
No mods to engine other than exhaust and air cleaner / breather.
Idle mixture jet has been uncapped and dialed in.

 

Connection to the primary helped my 97 Dyna. I’m not sure if I will rebuild it or replace it this winter. Only 20,000 on it. But the age is probably the culprit.