Can I target an :after pseudo-element with a sibling combinator?

You can't target :after since it's content is not rendered in the DOM and it does not manipulate it - for this to work the DOM would have to be re-rendered and CSS can't manipulate it like this.

No, you cannot target pseudo-elements with combinators relatively to their generating/containing elements or their real child elements. This is because they're pseudo-elements, not real elements.

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