No, not me.....yet, but this pic got me wondering. If we flip and even total our trucks off road will insurance cover it as if its totaled on a highway?

Depends on your policy. You should contact your agent to be sure. I know that most will cover if it is a FS road or the like. When it comes to trails, there is not really a one size fits all I don't believe.

While we are on the subject, are you guys carrying custom parts coverage on your aftermarket parts? Some of you have gotten up into the 10k+ range, a bit to much to just lose in an accident. Custom parts coverage does not cost too much extra.

if you pay your bill, and its not a timed event, they should cover it.
thats what insurance is for.

I have coverage for replacement of my aftermarket parts. Itemized with my ins. co (Geico).

Buddy of mine rolled his lifted and highly modded jeep on some of my farm trails with me a few years ago. Totaled it but insurance took care of it for him.

The difference between "should" and "will" could be financially disasterous.
If I wheeled my 4R, I'd for certain be taking Brock's advice.

Me, I don't assume ins. companies will cover out-of-the ordinary circumstances. I own a boat, and discovered that the fines for fuel-spillage (say your boat sinks) can be astronomical. A phone call determined that my boat is covered six-ways-to-Sunday, but not fuel spillage, and a very cheap rider now has that covered. Same with jewelry on your home owner's policy ... requires a rider.

Totally agree. Was in insurance for over 10 years. Non factory upgrades need to be itemized and valued separately or they will only cover damages as if stock. For that matter, if you carry liability insurance only (no comprehensive or collision coverage) your truck ain't covered at all unless another vehicle caused the damage to yours and you can make a claim against their insurance or them personally. And of course, don't trust me or anyone else's advice. Ask your insurance company/agent.

I will add a couple things in the form of "framing" some of the things already posted.
First, the Personal Auto policy wording (named exclusion) basically "covers" that which is not excluded so, get your law degree out and dust it off OR contact your agent and ask.
That said, follow it with an email stating " Based on our recent discussion, am I correct that the following IS covered......If I am in error please respond otherwise....."
"Upset" or "Rollover" is a physical damage coverage under the comprehensive portion of the policy. Where you want to zero in on is any exclusion that references "Intentional usage, Unimproved road surface, etc" It will vary by company and state so that is why you want to know first and get it in writing (email) BEFORE anything happens.
Now, you will hear people say (not here of course) that IF something happens just tow the rig to a place near a road and say it happened there.
DO NOT do this. Claim Fraud is a very serious offense and one that can lead to serious consequences far more serious than an Oh $h!t rollover.
Just cautioning in general, no inference to be drawn that I would think anyone would consider such a thing.
That's about it. None of my post was or is to be considered "Advice" of any kind nor is it a substitute for researching matters of a local, personal or general nature.
Good Luck.