Whoever packaged these is an idiot.

Gotta add better padding around and between the cookies themselves. That will do loads more than extra boxes. When cookies are touching cookies, and they’re dry sugar cookies, they’re going to break.

The real mildly infuriating thing is whoever boxed this hot mess. It doesn't take a braniac to notice that pre-packaged cookies you get in a store aren't just set in a box with wax paper.

Whoever sent cookies via mail didn’t think this through. That’s why cookies are usually wrapped in a plastic form to hold them in place and separated from each other or in a tight stack.

As others have already said, this ia a packing issue.

Cookies are relatively fragile. Double boxing with air cushions doesn't do much to prevent them breaking. It would prevent crushing damage to cookies, but that's not much of a worry tbh. If your box is getting crushed, something is going wrong.

Even if you transport cookies yourself, the biggest damage is from the cookies banging against each other. Layers of wax paper don't prevent that. Any lateral movement is going to completely negate that, and cause the cookies to end up on one side. That's what happened here, as you can tell from the oil stain on the box. The cookies slid against that side at some point, and that's all she wrote. They were then banging against each other with every bump on the road, every hard brake, and at any significant turns.

If you intend to ship cookies, there's a few ways to go about it. The first is the kind of wrappers you see in the famous tins of butter cookies that end up holding sewing supplies. Paper cups. They're pleated, and hold a small amount of cookies each. Those pleats insulte each stack from banging around. It's like bubble wrap for them. While it isn't perfect, it will allow you to ship most cookies with minimum breakage as long as you don't over stuff each cup.

You can go with plastic wrap instead. A stack of three to five cookies wrapped in plastic firmly enough to prevent them sliding inside the mini package, then twist tied will survive all but the most aggressive bouncing around. If you combine that with other packing material between those bundles, you're golden. I've never had an entire stack get broken when shipping this way.

Obviously, plastic isn't a great thing. But you can get close to the same protection with parchment paper and a little tape. But be aware it isn't as good for protection because the individual cookies are going to slide more inside each bundle. You just can't get the paper right because it doesn't flex and stretch as well.

Bundling small amounts and then packing those bundles in the package with shock absorbing material in between is the key to cookie shipping. It neutralizes most vibration, most sliding, and reduces all but the more severe impacts from things like dropping. That's when the double boxing with padding helps a little more. If there's a hard braking made during transport, the extra padding makes sure that the inner box isn't deformed, so there's no crushing of the cookies. And, it will make sure that reasonable amounts of weight won't do so.

I bake a good bit, or used to (this year has been rough in that regard) and ship the stuff to friends and family that I love enough to deal with going to the post office. It took a dozen failed shipments before I started figuring this out.

Which, as an aside, shipping iced cakes is still a fail. There's no way to secure the cake without the icing being ruined. I mean, you could use fondant I suppose, but doing that to someone you claim to love is just mean.

Cakes are a bitch anyway. Because they're just a lattice of air bubbles, any time inertia is applied, you get shearing. It can be done, but you can't guarantee an intact cake through any of the shipping options. You either drive it yourself, or risk loss. Cupcakes do okay when done like cookies, but individually wrapped with padding in between.

Pies are a hell no because there's just too much lateral motion in public shipping. Maybe something like a custard pie, but I wouldn't try that again.

Stuff like candies are fairly easy, though that's an obvious thing. As long as most homemade candies stay cool, they aren't going to break or be damaged at all.

Brownies and blondies do best when cut and packed like individual cookies. Never had more happen from that than the edges being a little smooshed.

I can't think of anything else offhand.

That's the way the cookies crumble. They go on quite a few rides during shipment.

You can tell me I am wrong in any of this and I will apologize immediately. That being said I think there is only one problem here

It appears the only thing keeping the cookies on the tray was a piece of wax paper and an air cushion. I think something happened to your wax film as it became loose and no longer contained the cookies. Possibly because of heat or condensation.

If the blot stain on the side is any indication, as it is absent from all other corners of the box. I believe your cookies ended up on their side completely unguarded from any wax film. Just cardboard, cookies, and whatever physics happened between here and there.

One way I would suggest to fix this is by vacuum sealing them if you wish to avoid this problem again. Though I imagine bakers and logistics experts will give you much better advice then this.

This package treatment usually isn't malice; the automated package sorting drops packages from one belt to another and the longest drop can be up to 12 feet (4 meters).

Always assume your package will experience such a drop when you're packing it.

Packing cookies too tight will break them from the pressure. Too loose and a light shaking will break them all.

That is done by the UPS VIOLENT SHAKER machine. Unique to UPS and done manually by all others.

Some assembly required

Amd thats why you put them in jars and deliver them in person. With a pipe bomb.

Well, make lemons outta lemonade y'know. They all end up the same size in the end, right?

I wish my browser had UPS