Dear Ryan,

In my business we have a few size shipping boxes. For example, use these sizes (in inches).

4x4x4
4x4x6
4x4x30
6x6x20
8x8x4
15x15x6
6x15x30

For all products, we know exact weight and dimensions. Thus, a product, which is 4x4x0.5 shipping clerk select 4x4x4 box.

We also know exact weight of the 4x4x4 shipping box. We add to this the weight of the foam peanuts packing material (to fill empty box).

Thus, if customer order several product, which are 4x4x.05, we know maximum qty 8 use 1 box. Weight calculation is pretty close because maximum discrepancy is weight of foam peanuts displaced and error is slightly higher actual shipping weight (instead of too little weight). Result is accurate enough for estimatation of shipping costs.

Moreover, when customer order a product, which is 1x1x29 plus several products, which are 4x4x0.5, shipping clerk knows to use box 4x4x30.

I wonder this, is possible for Drupal Commerce to determine appropriate box based on dimensions of products and shipping boxes?

This is useful because;
a) shipping clerk not required to think what box size to use
b) inventory shipping boxes (accurately re-order)
c) more accurately calculate shipping weights

Since computer is useful for repetitive calculations, and all package data is available, thus, if customer orders products requiring 4x4x30 and 15x15x6 the software may easily determines minimum box acceptable is 6x15x30, calculates shipping weight based on sum of shipping box weight + product weight(s) + packing material weight (for specified shipping box).

Many benefits accrue. Also important, Ubercart does not offer!

Not taking into account the weight of packages is a common issue. I believe that printplace suffered from the same problem a while back.