I use a Shadow Catcher material on a plane all the time with masks and alphas. If you set it up correctly, you can get all the layers separately, or you can even save an After Effects project file with everything already stacked.
I've attached a scene you can pick apart. You need to set your Shadow Catcher to Environment and Compositing. You must also drag a material into the slot provided, because if you had a white box sitting on that orange background, you would get some color spill. By making a material that matches you final background color for the poster ensures you will have the correct color that may be reflected on the surface of your box.
I've also enabled the Multi-Pass function. In the render settings, I also set it to save a Multi-pass image. This scene will give you 2 PSD files. You will have to do a little work, but not much. Just load the alpha channel as a selection and use the Float command to make a new layer based on your selection. You now have a perfect object(s) layer with a built-in shadow. The second PSD will have a clean mask just for the box in case you need to adjust the shadow.
As another option, if you select PNG as the output format, you will get all these layers as separate files. The only advantage to using the PSD format is that you could go up as high as 32-bit if you have very complex and subtle shadows and transparent areas.
Hope I didn't confuse you. Ha. That was a little rambling on my part.
https://www.dropbox.com/s/mqb39mpi1na9a2g/CompositingSetup.zip?dl=0