About 3 miles of twisty - and sometimes technical - singletrack, mostly downhill, in the dark, plus another mile of pavement. This was somewhere around 1990, with my first MTB. I flatted, replaced the tube, but then dropped and lost the schrader-presta adapter I needed for my pump. Without it, I was out of luck. I think that's the only time I had to walk. More recently, I was unable to repair a slashed sidewall of a tubeless tire due to a stuck valve stem nut, and had to call Uber. Other than those issues, I've always been able to take care of bike issues in the field.
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"Swedish fish. They're protein shaped." - livedarklions