The contexts and errors communicate information in different directions. Errors let upstream function know what happened within the call, context lets downstream functions know what happened elsewhere in the system. As a consequence there isn't much point to cancel the context and return the error right away if there isn't anybody else listening to it.
Also, context can be chained by definition. If you need to be able to cancel the context with a cause or cancel it with a timeout, you can just make two context and use them.
Example that shows the approach as well as the specific issue raised by the post: https://go.dev/play/p/rpmqWJFQE05
Thanks for the post though! Made me think about contexts usage more