@khurtwilliams Kudos for your tenacity! I just saw your notes on my site. The first http://boffosocko.com/2017/10/28/content-bloat-privacy-archives-peter-molnar/#comment-37986 appears to have been sent first as the webmention. The second two (http://boffosocko.com/2017/10/28/content-bloat-privacy-archives-peter-molnar/#comment-37984 and http://boffosocko.com/2017/10/28/content-bloat-privacy-archives-peter-molnar/#comment-37985) appear to have been input manually in the comment section of my site.
I'm guessing you didn't see (or possibly get the webmention--unless you're careful WordPress can often put webmentions into your spam queue) my other reply the other day that explained the issue. You can find it here (http://stream.boffosocko.com/2017/kh%C3%BCrt-ive-figured-it-out-then-id-seen-the-issue or here threaded into the commentary http://boffosocko.com/2017/10/25/your-licenses-frankly-my-dear-cogdogblog/#comment-37780), but I'll also manually syndicate my replies to you as well. Hopefully the explanation will solve your mystery.
By the way, once you fixed the URL on your first original webmention, it did come through and is listed in the Mentions subsection at the bottom of the comments: http://boffosocko.com/2017/10/25/your-licenses-frankly-my-dear-cogdogblog/#comments It shows up as a mention instead of a reply, because the URL that fed through was the raw one (i.e. without a class in the body of your response). If you fix the emoji portion and click save that URL will have a u-in-reply-to which should cause your response to show up and be parsed properly as a reply instead of just a vanilla mention).
If you'd like to discuss the subtleties of any of this in person, feel free to catch me on my phone number on my homepage. :)