Windows has a limit of total icon overlay handler can support "an image list can have up to 15 overlay masks".
If you have many applications that install icon overlay handler (such as Google Drive, OneDrive and etc), some icon overlay handler may be pushed out.
You can find existing handler list on the Registry:
and for 64-bit:
In the Registry, you can remove handler you no longer need.
Or you can just change the order on the list, putting in the top the ones you most use. To achieve that, you can rename the icon overlays registry (right-click -> Rename) and insert a few spaces at the beginning of the name.
This way, they'll show on the top of the icon overlay list. You may need to restart the Computer to this change takes effects.