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IMAP vs POP3 really is more for reading and if email reading is on one PC then POP3 makes more sense.
SMTP is for sending.
Make sure the same settings work in a regular email program like Thunderbird.
You have added your own email address to the Kindle Web page management? Not your own Kindle email.
Amazon only accepts sending addresses you have added.
Go Amazon -> Manage Content and Devices -> Preferences
Bottom of page: Personal Document Settings
Add any email address allowed to send to your Kindle.
Elephant in room!
Send To Kindle messes up the format compared to Calibre & convert to AZW3 and USB transfer
USB Transfer is faster and Kindle is charging. No Internet needed.
Send To Kindle gives Amazon a free copy of of whatever it is.
So multiple issues.
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