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During the past month or so, there have been about a half-dozen instances while driving that my Jeepster has a momentary (under two seconds) "cut-out" (I'd call it a hiccup) when the motor stops running and then immediately continues on as if nothing happened; if cruise control is on, it does not interrupt that; if the nightime lights are on, they are not affected; once or twice the cut-out has happened as I was in 1st or 2nd gear, starting up a hill; yesterday it was while on cruise at about 65/70 mph out in the middle of Eastern Oregon's wide-open freeways; my mechanic says he can only guess unless he can actually have the computer connection active at the instant it happens. My sense (fear?) is that if the instant suddenly was extended it would be the end of the motor – which would be quite disappointing since I’m at 337,000 miles (original motor & transmission).

Any thoughts?

Much appreciated.
 

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99 4.0. It may be a cracked manifold or a cracked head. With that many miles, when was the last time you have it a tune up?
It may be a throttle position sensor.
 

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My guess is that its a sensor. Either tps or cps. Something missing a signal intermittently and causing the stumble. But thats just a guess. Take a good look over your manifold for cracks, probably decent chance you find one, I just can't see the stumble like that being caused from it. Cracked head I also doubt but go ahead and look for coolant and oil mixing on one side or the other. Chances are that it would run pretty rough when hot if that were the case, and you'd have cylinders missing.

Tuneups are good, and pulling your sparkplugs might tell you something about the stumble behavior you see.
 

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Check your grounds. Don't just look at them actually remove the bolts holding them clean up the bolt and surface then reattach them. Might be a good idea to just replace your battery positive and ground cables if it's never been done. After you've done that I would start looking at sensors.
 
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