I wouldn’t necessarily say it was extra-adventurous considering the following 
rides mentioned weren’t exactly adventurous to begin with but twice 
(correction: thrice!) I’ve had cranks work themselves loose from bottom bracket 
spindles..  First was on a shakedown ride after some parts swapping along a 
frequent 6-ish mile loop in a local park and MUP system and I simply neglected 
to fully torque the bolts on the square taper cranks and was too eager to get 
some miles in.  NDS came loose about halfway and forgot my mini hex wrenches 
which I usually keep in a small tool kit.  Tried to tighten with an 
appropriately shaped rock but couldn’t get enough leverage no matter how I 
tried.  Return trip was essentially a one legged effort and fortunately on 
relatively flat terrain.  2nd time was a cottered crank where the nut on the 
old cotter worked itself loose on a Raleigh Sports.  This was in the early half 
of a planned summer leisure ride to get some dinner.  The nut was never to be 
seen again and we doubled back to load the bikes in the car and drive instead.

More recently I did a square taper conversion of a Raleigh frame using Raleigh 
cups and Italian spec square taper spindle.  Used NDS road crank appeared to 
get too close to the adjustable cup after a recent retorque and catch the flats 
to cause the cup to loosen and begin to push the crank off the spindle.  

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