I've found the coupon insert list over at CouponsDealsAndMore to be most helpful. Scroll down to the bottom of the post to see the oldest inserts first. Then work your way through your coupon files, pulling any inserts that no longer have valid coupons. If you need the extra room in your file, you might consider cutting out the 1 or 2 coupons that are still valid and filing them away with your other loose coupons.
Oh, and before you just toss the old inserts out . . . if you have kids (or grandkids), there are many great teaching opportunities to be had with them. My 4 year old, Isaiah, loves "school." He asks me every day when he gets up if he can "do school." Today we searched through my inserts to find the different colors of the rainbow (red, orange, yellow, green, blue, purple). He cut out the colors that he found and sorted the cut paper into piles, until he had a pile of red, a pile of orange, and so on. He then glued the pictures, in the order of a prism/rainbow, onto black paper.
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