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Correct, I set up a workflow to fail (no logic in a query) so we could see the alert to make sure it works. Now that I'm taking a closer look at this instance compared to another, I see a working instance has Population from a file in the To line and this non-working instance has a specific set of email addresses called out. When I look into the file it's referencing, the values are defined there and I can now preview the delivery. I can't send it still, but a preview of it works. I'll just keep messing around with it, this was clearly adjusted by someone though because it no longer matches the stock template.
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