The shipping calculator only send dimensions to the respective shipper APIs if the items are set to "Ships Individually".   We have dimensions set for almost every product in our database that is over 12", but none of those get sent to the shipper APIs.  We don't want to set every item over 12" to "Ships Individually" as that will greatly overcharge shipping on most order.
We are dealing with this issue every day.
We currently have a quote from AmeriCommerce to always send the max dimensions in a cart to the shipper APIs for quotes.  It also included adding max dimensions for custom shipping methods. 
The quote came back as $8,000 and estimated to take 12 weeks to be ready for testing. 
Here is my request to AmeriCommerce:
.: Request 1 :.Add max allowed dimensions for a custom shipping method (Example: we have a custom shipping method setup for UPS Mail Innovations, which has a max package size of 12x12x12, but there is currently no way for us to limit package size for custom shipping methods).: Request 2 :.Hide a shipment method if the dimensions of an item on the order exceeds the max allowed by the carrier for that shipping method (Example: UPS Express to Australia cannot ship an item if any of the dimensions exceed 36").: Request 3 :.Provide the maximum dimensions of items in the cart to the shipping carriers for more accurate shipping quotes.Example, 4 items in cart: 12x8x12 (sorted largest to smallest as required by carriers, 12x12x8)3x6x16 (sorted largest to smallest as required by carriers, 16x6x3)16x20x4 (sorted largest to smallest as required by carriers, 20x16x4)10x12x12 (sorted largest to smallest as required by carriers, 12x12x10)AmeriCommerce should sort each L x W x D set largest to smallest and then report largest in each variable to carrier, in this example reporting the dimensions 20x16x10 for the shipping quote. Doing this should also accomplish Request #2 above as well.Add some logic that could check when a cart is over dimensions, if there is a combination of the products in the cart that is shippable.Example cart:42x8x12 (sorted largest to smallest as required by carriers, 42x12x8)3x6x16 (sorted largest to smallest as required by carriers, 16x6x3)16x20x4 (sorted largest to smallest as required by carriers, 20x16x4)4x32x32 (sorted largest to smallest as required by carriers, 32x32x4)If shipping this order to Australia, 42x32x8 exceeds the max allowed for USPS, but 42x16x8 and 32x32x4 would be allowed via Priority International.