Somehow I can't pin anything to my Start Menu apart from software listed under Apps.

For example, when I right click on the "This PC" icon, there's a "Pin to Start" context menu. However, it doesn't work whenever I click it as the icon does not appear on the Start Screen.

And I've been using OblyTile to customize icons on my Start Menu, and the icons I've created with it does not appear on it.

Any advice is much appreciated!