Currently there is a lack of clarity on when we should be preserving calc() for specified values. For instance, we preserve it for `width` but not for `color`. This tracks getting an answer from the CSS WG on the issue and can be used to host test cases.
Created attachment 464424 [details] Test
Filed https://github.com/w3c/csswg-drafts/issues/8290 to track the issue with the WG.
So the answer is we should always be preserving calc() in the specified values, and our behavior for colors in the test case is wrong. In practice this means we should be really remove all of the "Raw" helpers in the CSS property parser and ensure we have mechanisms to preserve calc in the respective CSSValue types.
<rdar://problem/104301484>