Currently "Out of date" it is not shown, when adding objects to the workspace. Only when objects are already in the workspace the column(and such information) is available. It is not a very big problem with simple files, but can be quite confusing when working with big projects.
On the screenshot you can see the example. The objects exist already in revision "E", but when adding version D.8 there is no information that it is an older object. When adding D.7 (not latest in "D" revision) there is an information - PTC shows this only for non-latest objects of current revision.