How to know when it's time to recycle expired inserts
There's never been a better time to be a coupon shopper, as there's a coupon tool online for just about everything.
Here's a great link for determining what you need to keep and what you don't -- CouponTom's Current Inserts. (Note that this link also shows which issues of All You magazine have unexpired coupons inside too, if your coupon arsenal also consists of a subscription to All You.)
Browse to that page and look at the green box on the left. If an insert's name and date appears in the list, it has unexpired coupons inside. If it doesn't, everything inside is expired, and it's safe to get rid of it.
(Click the box to see the entire list -- I'm showing only a sample portion of it.)
You can also click the date/name abbreviation for that insert to see an entire list of the coupons the insert contains, as well as which ones are still unexpired.
What to do with expired coupons (other than recycle them):
If you would like to help military families living overseas, the Overseas Coupon Project is a great way to help them save money. Military families living on U.S. bases outside of the country can use expired manufacturer coupons up to six months after the date. Because it does take time to ship and sort the coupons once they're received, they ask that you not send coupons that are more than two or three months past their expiration dates. They also do not want whole inserts -- they want clipped coupons sorted into two groups: grocery, and non-grocery.