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Looking at your posted log, you are not able to use DNS to resolve the smtp server address when connected to the VPN. You might want to check what DNS servers are in use when you are connected to the VPN and if you can ping the smtp server when connected to the VPN.
Also I'm not certain you can email directly to a kindle.com address. The only time I've tried it, I have used a gmx.com SMTP server to forward the email to my kindle.com address.
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