My 96 NV4500 does the same thing... only in both hot and cold... LOL Actually the only time it grinds cold... is from a cold-soaked (below zero) start... then goes away... then comes back again when shes warm.
Doesnt do it all the time... and it does it more when I speed shift it... if I ease the stick into gear... shes ok... but when I speedshift... . she'll grind.
Grind isnt all that bad... just lets u know its there. .
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124,000 on the truck, (been grinding since about 92k or so) transmission fluid due to be changed.
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"Shadows" 96' 2500 SLT, Reg Cab, 12V, 4x4, NV4500, 4. 10s, LB, LSD, Black Exterior w/chrome rockers, Camel/Tan Interior, Towing Pkg w/ Tekonsha electric brake controller, Walker Muffler, Kitty wandered off to the woods...

K&N Filter--Silencer Ring gone,AFC opened up a bit, Optima Yellow-tops, 235/85/16 Michelin LTX A/Ts Other Upgrades pending $$$$
TO THE BOMB BAY!!!!!!!