Hi Doc:
I'm not sure what's going on with your truck and filter. Sounds like you might have the wrong fuel filter. I've always used a Purolator F55055 in my 96 PSD ever since I bought it.
The Purolator F55055 that I buy comes as an all-in-one lid, gasket and filter. The top of the filter lid has a 1/2" female square drive that allows you to use a ratchet to remove and snug down the lid. Just be careful not to overtighten the lid (it's easy to do using a ratchet) and be sure to lubricate the gasket with clean diesel fuel before installing.
One thing I normally do before I change the fuel filter is drain the water from the bowl. By doing this, it lowers the level of diesel fuel in the bowl and makes the job of changing the fuel filter a little less messy.
I don't know if any of this will help in resolving your problem but this is what I have used over the years and it works for me.
Good luck!
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2009 GMC Sierra 2500HD | Crew Cab | Standard Box | 4WD | Duramax/Allison
2000 Jayco Eagle 266 | FBS | TT
1986 Coleman Laramie pop-up -- Still in the family!!!
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