I can't tell you how, but here's what happened (years ago):
I prepped my truck for a long trip. Part of that preparation was draining 'the water' from the fuel filter. As I went up hills, I began to lose power. I crossed the Appalachians (non-interstate) in 3rd gear barely doing 30mph with my flashers on, hoping that I didn't break completely down on the steep grade. I pulled off the road after cresting the top as soon as a spot became available and couldn't find anything blatantly wrong. She was hard to start right then, but ran okay for a while. Still had some power loss on small hills. Within 80mi somewhere in the hills of KY she bogged out completely and off to the side of the road we coasted. She did not restart this time. I spent the next ~10min or so trying to figure things out. I eventually pushed the manual primer; she barely fired up. While temporary relieved, I drove (with the truck preforming poorly) to the first fuel station I came across and parked. About an hour+ later (*sigh*), I thought about that WIF drain. There was some diesel fuel on my lift pump & starter (I had attached a hose during my maintenance, so the wetness was new). The leak couldn't have been too great, because I hand calculated 22+ mpg's on that specific tank of fuel. Anyway, after cycling the drain lever several times and insuring it was fully seated, I fired her up (forgot to prime on the first attempt!) and continued my trip. I drove the next 300+ miles without incident, including going up the long grades of the national forest in eastern IN that I-64 traverses. Ordered up a new drain assembly the next day.
The only things I messed with at the station in KY were the lift pump primer and the WIF drain assembly. I spent most of my time reading up on possible solutions and staring into the engine bay, lost in various thoughts.
After installing the new drain assembly, I haven't had starting/bogging issues since (well, I did have a loose positive cable connection at a totally separate point in time that caused a click followed by the sound of silence...).
When I noticed my drain assembly with a tiny amount of diesel seepage years later, I deleted it. Didn't feel like taking the chance and didn't like the fact that it began to fail again after just a few years.