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For the record, I've been having the same email to kindle issue as everyone else. I've just been slack about getting around to trying to figure out the problem. I have a gmail account and I've been using Calibre to send via Amazon to my Kindle for years.
I read the fix offered by adoresReading and tried it on my PC. It did not work and test email failed. So I reset the server settings back to what they were (mostly blank except for Port 25 and Encryption TLS.) Now test email works fine again but I still can't email to my Kindle.
I created a gmx account and set it up per the excellent FAQ by Kovid. I did not have a gmx account before, but it was a simple process to set a free account up and configure Calibre to use it. Just use your gmx email address as both your email and user name.
Now Calibre is working just fine sending books to my Kindle again! And I also changed the delay from 301 to 5. I hope that doesn't get me flagged. I don't send that many books, so I expect that won't be a problem. Also, I did not have to allow less secure apps. So that was a plus.
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