I ordered a large number of cookies (320) that were shipped from across country. I can tell you how not to ship a large amount of cookies from the way they did. The cookies that we ordered were to be the four Aces from a deck of cards. We ordered 80 sets of four and requested that each set be packaged separately. The cookies that were made were very nice, they were about 1/2" thick sugar cookies about 3"x5" or so in size. They were covered in white icing and then the letters and symbols were hand piped. They were placed on small cardboard boxes with a glassine covered opening, with a "Thank You" sticker sealing the boxes (the cookies were thank you gifts for our bridge club. They then put bubble wrap on the bottom and top of two boxes (one much larger than the other) stacked the cardboard boxes in the larger boxes and shipped them. About 10-15% of the cookies came broken. The reasons for this were several. First, the large boxes were not nearly sturdy enough (just basic moving boxes). A box with much thicker cardboard was required. Second, there was no padding on the sides. All of the cookies facing the sides came broken (the heart Aces tended to be the last ones they put in the boxes so they were the main casualties). Third, the individual cardboard boxes that the cookies came in were too flimsy. The weight of the cookies crushed the boxes on the bottom layers, again resulting in broken cookies.
As I had agreed to pay reasonable shipping, in addition to the cost of the cookies, these problem could have been easily solved. The small boxes of cookies should have been put in a sturdy box with a layer of cardboard and bubble wrap between each layer of small boxes. The sturdy box should have then been placed in a larger box with padding (bubble wrap) on all six sides between the two boxes. I think this method of shipping would have resulted in fewer cookies being broken. They did actually put a lot of tissue paper between the individual cookies in the small boxes, which kept the cookies behind the cookies on the outside of the big boxes from being broken.
The cookiers were very nice about it and refunded the price of all of the broken cookies and fortunately, there were enough people who didn't want or failed to pick up their gifts that we didn't have to stiff anyone because of the breakage. Another good idea for a really large order would be to include a few extra cookies to account for any breakage during shipping.
BTW broken cookies still taste as good as unbroken ones.