Is it possible to create a Context Menu item in Windows 10 like a Checkbox?

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More specifically, I want to right-click on an image file and then click a Context Menu Item that will enable a certain property of that file. I'm designing a wallpaper changer program and the images I enabled on the Context Menu will be accepted by the program as a valid image to be used, otherwise, the program won't use the image.

A good example of what I want would be the "Lock all taskbars" when you right-click the Taskbar. To uncheck it allows you to move the Taskbar however you want it on your display.

I'm sure this involves creating a new item in the Context Menu within the registry, but is there any way I can have this checkbox function when right-clicking a file?

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