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I ended up refitting it as per original setup but with carbon assembly paste, as per my original pic, with the bung about 40mm down, well below the top of the stem, as the sleeve on the compression bolt forces you to.
It's not slipped again - if it does I'll probably replace the bung with the oversize Pro one someone linked to.
Dredging up an old thread, but did you ever figure out the answer to this? I've got the exact same question about the compression plug on my Canyon. It seems like the plug is too shallow to cover the entire area where the stem is clamped.