Here's a way to present two closely-related options with a single checkbox with 4 distinct states.

It is very rarely (if ever) that anyone would need to copy Owner information without also copying file's Group info. However, these are separate bits, so bunching them together doesn't seem like a right thing to do. But giving each of them their own piece of UI real-estate doesn't feel right either.

So how can we pack them up?

First, let's look at how this can be done conventionally. We'll just be verbose about it and list all the options as is: This is OK in terms of usability, but when taken as a part of the whole it makes window look cluttered: And *unnecessary* cluttered at that, because in a vast majority of cases Owner and Group will be either both checked or unchecked. Ditto for Security and Audit options.

So let's try something else.

Windows natively supports something called "3-state" checkboxes that can be in checked, unchecked or indeterminate states. "Indeterminate" is a rather strange term as if the program is not sure in which state the option is. However we can think of it as an in-between or partial state and do something like this: This is not bad, however we lose the overall meaning of the option when it is in a partial state: So let's put the context back: Better, but now we are back to things being too verbose and looking cluttered. Let's simplify it for two most common cases: Better, but now it's off visually: How about with chop the specifics and move them to the side: Almost there, just need to patch up visual hierarchy a bit to help telling principal parts from the secondary ones: And that's it. The result is an UI that looks clean and simple for two most common cases, fully supports marginal ones and packs 4 options in a space of two.
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