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When I first started shooting ten ga. I did not have much money and no source of empties to reload. So I would haunt the back country hardware stores for old ten ga ammo that they had not been able to sell. Plastic had not been invented yet for shotshells (yeah, I'm that old). I could get short shells for $2.50-3.50 a box and once in awhile a box of long ones for $4-5. Sometimes they would be in old boxes that collectors would die for today. At least 20 years old and some 30 or more. Almost always roll crimped. Factory loading almost always fired fine. Once in a great while a bad primer.

Since I was waterfowling, keeping the powder dry was a concern. So I always rewaxed the cases in hot parafin before the first reload. Using Winchester/Hogdon ball powder I could get 3-5 reloads out of them before the mouths would tatter from star crimping. Herco would pinhole the case at the top of the brass after the first or second reload.

To answer your original question, I wouldn't hesitate even today to fire old paper shells that show no signs of swelling or other damage. I wouldn't use them in competition because you may get an occasional FTF or squib. And they will reload fine at least once. The dark shot coloration may be caused by the original graphite coating on the shot.
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