'Send to Kindle' Function Malfunction

monophoto · 11-04-2022, 08:13 AM

I attempted to have Calibre transfer a book to my Kindle reader this morning, and received the following error message:

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 47, in run
File "calibre\gui2\email.py", line 136, in sendmail
File "calibre\utils\smtp.py", line 162, in sendmail
File "calibre\utils\smtp.py", line 142, in sendmail_direct
OSError: Failed to send mail: SMTPRecipientsRefused({'XXXXXXXX@kindle.com': (550, b'5.7.1 IP address blacklisted by recipient')})

I was able to generate an e-mail in Outlook that successfully reached my Kindle.

Am I correct in interpreting this to mean that Amazon's 'Send to Kindle' server is rejecting e-mails originating at Calibre?

DNSB · 11-04-2022, 11:32 AM

Try using an email relay instead of trying to send directly to your Kindle email address. I'd suggest GMX since it's relatively easy to set up. Just remember to enable POP/SMTP in GMX's setup.

And no, it's not rejecting emails from calibre, it's rejecting emails coming directly from your computer's public IP address.

Quoth · 11-04-2022, 12:15 PM

Some UK ISPs only allow their SMTP server and block SMTP to any other Mail Exchange / Server / Relay.
Some ISPs that offer SMTP server only allow requests from their own IP addresses, so when you leave home or office and are on a different ISP, you can't send email.
Some email systems may block the entire IP range of an ISP if that range has a lot of spammers. Sometimes they block an IP range they think is in that and isn't!

11-04-2022, 08:13 AM	#1
monophoto Connoisseur Posts: 52 Karma: 2492712 Join Date: Jun 2022 Location: Saratoga Springs, NY Device: Kindle Paperwhite, Amazon Fire HD8 (2020)	'Send to Kindle' Function Malfunction I attempted to have Calibre transfer a book to my Kindle reader this morning, and received the following error message: Sending failed... Traceback (most recent call last): File "calibre\gui2\email.py", line 47, in run File "calibre\gui2\email.py", line 136, in sendmail File "calibre\utils\smtp.py", line 162, in sendmail File "calibre\utils\smtp.py", line 142, in sendmail_direct OSError: Failed to send mail: SMTPRecipientsRefused({'XXXXXXXX@kindle.com': (550, b'5.7.1 IP address blacklisted by recipient')}) I was able to generate an e-mail in Outlook that successfully reached my Kindle. Am I correct in interpreting this to mean that Amazon's 'Send to Kindle' server is rejecting e-mails originating at Calibre?

11-04-2022, 12:15 PM	#3
Quoth the rook, bossing Never. Posts: 11,699 Karma: 87663461 Join Date: Jun 2017 Location: Ireland Device: All 4 Kinds: epub eink, Kindle, android eink, NxtPaper11	Some UK ISPs only allow their SMTP server and block SMTP to any other Mail Exchange / Server / Relay. Some ISPs that offer SMTP server only allow requests from their own IP addresses, so when you leave home or office and are on a different ISP, you can't send email. Some email systems may block the entire IP range of an ISP if that range has a lot of spammers. Sometimes they block an IP range they think is in that and isn't! Last edited by Quoth; 11-04-2022 at 12:17 PM.

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11-04-2022, 11:32 AM	#2
DNSB Bibliophagist Posts: 36,857 Karma: 147879470 Join Date: Jul 2010 Location: Vancouver Device: Kobo Sage, Libra Colour, Lenovo M8 FHD, Paperwhite 4, Tolino epos	Try using an email relay instead of trying to send directly to your Kindle email address. I'd suggest GMX since it's relatively easy to set up. Just remember to enable POP/SMTP in GMX's setup. And no, it's not rejecting emails from calibre, it's rejecting emails coming directly from your computer's public IP address.

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