Sounds like you have to enable the jump list
Follow this and make sure that it is ticked or unticked per your needs
1. Right-click on the taskbar and select “Properties”.
2. In the “Taskbar and Start Menu properties” dialog box, switch to Start Menu tab.
3. Deselect the option named “Store and display recently opened items in the Start menu and the taskbar” to disable Jump Lists feature.
4. Click on the “Apply” button to save the changes.
5. Recheck the box to enable the same feature.
Jump Lists - Reset and Clear All Items