Mildly Infuriating

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.