Users are reporting issues with the “Watching First Post” notification feature on tags not working reliably. zjpcyo and abrain have experienced this issue with the release-notes tag, where they only received notifications for a single post despite being subscribed for an extended period. Stephen suggested that the issue may be isolated, but JammyDodger confirmed that the problem persisted with a subsequent topic. nbianca later identified the root cause: the tag notification was not created when a topic was created from a shared draft, and has since fixed the issue in a PR (https://github.com/discourse/discourse/pull/17576).
I don’t think there’s sufficient evidence here to suggest that it isn’t working.
One of the team could check in your specific case as to whether email was sent to your account, as it stands though you’re the only person reporting a problem.
I am watching the release-notes tag (not just the first post) for quite some time. And the 2.8.5 Security Release was the first and only one I got notified about.
It does not seem like an email issue to me, because my notifications here on the site also only show the 2.8.5 release post.