Hi Travis,
We created a helpful KB to guide you in this regard. Please check out https://confluence.atlassian.com/jirakb/how-to-collect-data-for-atlassian-support-for-troubleshooting-jira-webhooks-397083035.html
It explains some steps you can take to test this out. There are some logging levels that you can turn up in Jira in order to see the debug level logging of these webhook actions. By default, Jira doesn't usually log these webhook actions in it's own logging.
I hope this helps.
Andy
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