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I just did some quick testing with a gmx account and sending multiple books. The first book sent happily enough, the second book sat and never sent (original test waited 4 minutes, the second test waited ~2 minutes). After stopping the other send jobs, I had to restart calibre before it would let me send another book via email.
After the restart, I sent to gmx again and the same one book sent the next one just waited. I switched to my usual ISP and no issues with sending the 4 books. See attached image.
For the fun part, I switched back to gmx and the 4 books sent without issue. Perhaps that I hadn't used GMX in quite a while?
Anyhow, I have to say it is probably a GMX issue.
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