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    Ben commented  · 

    It looks like Airmail uses Drafts as an Outbox. When messages don't sent, they are marked as "waiting" under Drafts. They can get stuck that way with no warning that they didn't send and they won't show up in searches. I only discovered this when I looked at my drafts for a different reason and discovered a bunch of messages that had not sent and that I had never saved as a draft. Details can be found here:

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