Let me explain what the "Expand folder shortcuts" setting does as it's not clear from its description although it's functionality can be very valuable.
First, in Classic Shell 4.0, you can select between 2 folders where pinned shortcuts go - either the dedicated Pinned folder (%appdata%\ClassicShell\Pinned) or the Start Menu folder (%AppData%\Microsoft\Windows\Start Menu). This setting is there on the Main Menu tab -> "Pinned Programs folder".
When this setting is set to "Use Start Menu folder", then dragging and dropping a folder from the Desktop or from any other location on the file system to this Start Menu folder (or its subfolders such as Programs) creates a special symbolic link shortcut. Only Windows can create this shortcut, not Classic Shell. It is this shortcut that can be expanded by the Classic Start Menu when the "Expand folder shortcuts" setting is checked.
Only the Start Menu folder (and its subfolders such as Programs) have this special behavior since Windows 95. Another way to create this special sym link is to open the Start Menu folder in File Explorer, then right click on any folder on the file system to which you wish to create a shortcut, click Copy and then click "Paste shortcut" inside the Start Menu folder or Programs folders in Explorer. Once this link is created in these special folders, it can be moved to another location such as the Pinned folder if you switch back to using it. The shortcut still remains expandable.
If you create a shortcut to a folder in any other location except the Start Menu folder or Programs, the shortcut created will be a plain shortcut which doesn't expand, it only opens in a new window in Explorer.
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