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I have a 99' Ram 2500, and I have P295/75/16 BFG AT KO(33.4") with a little rubbing in turns. I got a 2" skyjacker suspension lift so I could run 33" Super Swampers (2nd set) and chains with my BFG's. You should be ok with the 285/75/16's, but you might run into trouble if you put chains on the front.
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