WIF or O Ring failure would cause air to be sucked in and the truck would SHUT OFF....ask me how I know lol.
I've experienced the poo87 when pulling heavy through the mountains. AirDog 165 II lift pump/filter-water separator has solved it for the last 5-6 years. Added a fuel pressure gauge so I could monitor filters. I run at 8-9 psi and when I see <6 I change filters. I usually get 12-18 months out of the Airdog filter. I go ahead and change the OEM filter while I'm at it. I run mostly bio-diesel for the last 115k or so.
Hope you get it fixed.