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I don't worry about expiring coupons only RR's (from Walgreens), cats and ECBs (CVS). I file my inserts by date and only clip what I know is going to be a deal that week. If there is something I know I need to get that is not on sale, I'll use the coupon database (and on other coupon boards) to see if there is a coupon available and then clip it. This saves tons of time and if I miss a clearance deal, oh well.
There is a lady who I took a coupon class from who uses the same method with one difference. She cuts out all the q's in one set of inserts and carries those in her binder. That way she always has at least one q with her to take advantage of clearance deals.
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