Prefabs with empties can't surface snap?

When I begin assembling a prefab from primitive Unity objects, I can translate the parent object --the top-level empty-- with surface snapping and the editor takes into account the colliders of all the child objects. However, somewhere down the line, as I add objects, it stops taking these into account and only snaps regarding the empty. Is this a bug?

I do have center tool mode on as well as global rotation, and vertex snapping seems to be working correctly as well. Unity version is 2020.1.13f1 on Windows 10 Pro box with DX12

Thank you for your time,