There are multiple other posts floating around in the forums regarding dimensions and real time shipping When using real time shipping, dimensions are only sent if the items are marked in the admin section as Is Ship Separately. If they aren't, then dimensions are not taken into consideration as it's assumed that each of the items will be going into a single larger box of unknown dimensions. If you have a specific set of business rules that are going to require sending the dimensions of one box and determining which items will be packed together in the same box that you'll need to get a copy of the source code and probably make modifications in both the ShoppingCart and RTShipping classes to support this. If your items are shipping individually then you can just set Is Ship Separately to Yes for each of the items and then dimensions will be sent over.
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