Twelve Cupcakes Went In and Only Nine Came Out Straight
A cupcake tips. That is the whole problem. Once it tips in the car, frosting hits cardboard and there is nothing you can do about it then.
A flat tray with no dividers is basically asking for this. Sharp turn happens, every cupcake slides into the next one. Good cupcake boxes stop this from happening before the lid even closes.

What Does a Fitted Insert Actually Do?
It stops them from moving. Nothing more.
A flat base gives the cupcake nothing to grab onto. So it slides. An insert is different. It has its own hole for each one. The cupcake sits in that hole and that is where it stays. The wrapper does not touch other wrappers. Frosting does not smear.
How does that work? Each cupcake gets its own little pocket, molded specifically for a standard cupcake size. You drop the cupcake down into that pocket and it cannot move left or right or forward or back. That is really all it is.
Inserts can come as a separate piece that slides into the box, or they can be molded as part of the box itself. Both work fine. The separate tray is easier to replace if something breaks.
Match the Holes to How Many You Are Actually Selling
Six cupcakes rattling around in a twelve hole insert? They will still slide. Five empty holes are five chances for them to move sideways.
So do not buy the wrong size. Buy the right size. Six holes for six cupcakes. Four holes for four. This is not complicated but people skip it all the time.
Odd numbers matter too. Four cupcakes in a six hole box means two empty spots. The box looks half full and the cupcakes still move. Get a four hole instead. The box looks right and nothing moves.
What Happens When the Window Presses on the Frosting?
Sometimes it does. Depends how tall you piped it.
A window cut works fine if frosting is flat or only slightly domed. Pipe something tall, something with a swirl, and the window touches it the instant the lid closes. All that work smearing flat against plastic in one second.
So measure first. Measure the peak of whatever frosting you put on top. Not the cake height. The frosting height. Then buy a box with enough clearance above that.
Frosting styles change? Keep two sizes. One for flat, one for tall piping. Costs more but saves a ruined batch later.
Stacking Boxes Destroys the Bottom Layer
Weight just goes straight down. A normal cardboard lid is not built to hold another box on top of it. So it flexes. The cupcakes below tip and slide and touch each other.
Some boxes have internal columns or reinforced lids. Those can actually be stacked. Most cannot.
So check. Before you put four boxes in the back seat, ask the supplier if cupcake boxes are rated for stacking. If not, lay them flat instead. A car boot usually fits two or three flat. That is safer than hoping the lid holds.
One Box First
Put an actual cupcake in the box. Do this a few days early, not the night before a big order. You will know straight away if the depth, the hole spacing, and the window height all actually fit together.
Skip this step and you find out the problem the night before delivery. When nobody at the supplier is answering the phone.
Ask the supplier to send one sample box if you can. Most will. It is way cheaper than remaking fifty cupcakes because the box does not fit.