This actually stems from the GitHub side of things:
Note: You will not receive a webhook for this event when you push more than three tags at once.
Since we rely on a GitHub webhook to trigger builds, and the above notes that one isn't generated when 3 or more additional tags are involved, this would be a case where you would not see a build triggered in CircleCI.
You will want to ensure you are only pushing up to three tags at a time if you want builds triggered within CircleCI.
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