It would never occur to me to ask a store to honor a coupon after it expired. Upgrades are not comparable. Disney is also not known for offering upgrades free just for asking. They do offer them sometimes, but asking is not the best way to get them. The tone of the first post appeared to be a complaint because they refused to honor the offer after it expired. I woudn't expect them to.
I don't know of anyone who was able to get free dining after it expired just because they didn't call while the offer was still good. Not that there isn't anyone out there but I don't recall seeing it on the boards.
Target does it all the time. Right at the checkout...no need to even take it to the customer service desk. I found this out by accident - I had two coupons for $5.00 off a purchase of $50.00 or more, and gave her the wrong one. Before I could even give her the correct one, she said not to worry about it, pushed a few buttons, and overrode the error.
OP - I never expected the lady at Target to override anything for me, either
It never hurts to ask!