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Blargh, I just figured out what the problem was. Hat tip to this fine fellow for the clue I needed: https://github.com/juretta/hudson-github-plugin/issues/4#issuecomment-56458604. The bug is actually a case-sensitivity issue.
The log entries I included in my issue description were a red herring: a webhook was automatically created (I just missed it), and was being fired from GitHub as expected, and was even being received by Jenkins. Unfortunately, though, Jenkins was ignoring the hook events, because my organization name in Jenkins was cased as HHSIDEALab, rather than as HHSIDEAlab (which is how it's cased in GitHub and in the hook events).
Hilariously, this blew a whole day for me. I know it's a super minor problem in the grand scheme of things, but if you folks could fix the issue, or at least add a useful error/warning in the logs, that'd be super helpful to "future me"s.
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