Bugger.
i guess as long as I知 going to ride roads like this, I知 going need a skid plate.

Put a rock through the oil pan.

 

Looks like you need a pan am! That痴 some crazy roads for a softail lol

 

Ouch that's an expensive "well that sucks."
Part of riding off road is knowing the limits your bike has and what line to pick through a path as to not hit things, but ofc that's nowhere near easy to do.

Hogworkz makes a skidplate that I've been eyeing at https://hogworkz.com/hogworkz-black-...oftail-m8.html

 

I almost bought the Pan Am. But compared to the Heritage, it's a tall bike for me, and certainly has its own issues. Around here, roads like this are darned rare, and often not a pretty ride. So normally I don't go down them...normally.

Anyhow, I really should have listened to that cautionary voice in my head that said something like "this doesn't look like a good idea". 😆
But, the little boy inside my head was shouting "go for it" and "you can do it!"
Little boys are always silly. Even the ones in older mens heads.

The bottom where I came out (and took that picture) makes it darn clear what you're getting into, and why you shouldn't.
The top, where I did enter, was all leaf covered, and not that bad. Then it dropped steeply down while getting rather nasty. It was where turning around and going back was dubious. So, press on!

The bike handled it all with great aplomb. I really was surprised at how well it was doing. Which, in part, may have contributed to the damage. I wasn't going super slow, because I didn't need to.
No, I wasn't trying to mountain goat over stuff, just riding it. But the bike wasn't slithering and wasn't vicious with wheel kick or stuff either. It was actually pretty durn easy going.

Which "bang" punched the hole? Can't say. Can guess in hind sight, but really only because the rear end started slipping off rocks at the end there, probably because of the oil on the tire.

It was a slowish leak, so I never lost oil pressure, no odd or ugly engine sounds. Did make going around turns interesting as I rolled down into a little hamlet that a tow truck could get to.
Nice folk down there. They regaled me with tales of crashes and failures on that road, and could hardly believe I'd gotten that bike down it.
Was given snacks, some home made candy brittle, water, etc. Even invited in for dinner, and possibly more if a tow couldn't be arranged.
But conveniently, one of the folk there ran a towing business on the side, so they brought me home.

All in all, a surprisingly nice day. If a bit expensive.