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Shipping multiple products into a different box


Hi Everyone,

I just migrated from ShipWorks to ShipStation. Everything seems better except for the fact that I cannot automate shipping orders with multiple products. I have uploaded all the correct box sizes for each individual product. However, if someone orders multiple products, the box sizes change. For example, Product A will ship by itself with Box A and Product B will ship by itself in Box B. However, if both Product A and Product B are purchased together, I need it to ship in Box C. We almost exclusively use custom box sizes.

In ShipWorks, I was able to do this, because it remembered previous shipments based on the SKU's in the order. I have contacted ShipStation support and they barely understood what I was trying to achieve and ended up getting back to me after discussing with their team saying this was not possible. 

Has anyone figured out a way to achieve this? This seems like a pretty standard feature a shipping software should be able to achieve as people like to order multiple things at once. 

Thanks in advance!