sharing by email fails

[ayjay3]

I have used Calibre's share for years now but trying to email to existing uses is failing with an error message:
calibre, version 6.1.0 (darwin, embedded-python: True)
Failed to email book: Failed: Email Oh William! to asjolly@kindle.com

Starting job: Email Oh William! to asjolly@kindle.com

Sending failed...

Traceback (most recent call last):
File "calibre/gui2/email.py", line 48, in run
File "calibre/gui2/email.py", line 137, 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({'asjolly@kindle.com': (550, b'5.7.1 IP address blacklisted by recipient')})


Retrying in 1 seconds...

Waiting 1 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks

Sending failed...

Traceback (most recent call last):
File "calibre/gui2/email.py", line 48, in run
File "calibre/gui2/email.py", line 137, 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({'asjolly@kindle.com': (550, b'5.7.1 IP address blacklisted by recipient')})

Job: "Email XX to xx@kindle.com" failed with error:
Traceback (most recent call last):
File "calibre/gui2/threaded_jobs.py", line 82, in start_work
File "calibre/gui2/email.py", line 105, in __call__
File "calibre/gui2/email.py", line 48, in run
File "calibre/gui2/email.py", line 137, 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({'XX@kindle.com': (550, b'5.7.1 IP address blacklisted by recipient')})

Called with args: ('/var/folders/w4/xd9lwy0j3yv623gvfwlrcq5w0000gp/C/calibre_6.1.0_tmp_45ikymje/wp529l67caltmpfmt.EPUB', 'XX.EPUB', 'asjolly@kindle.com', 'E-book: Oh William!', 'Attached, you will find the e-book\n\nOh William!\n\tby Elizabeth Strout\n\nin the EPUB format.') {'notifications': <queue.Queue object at 0x125589c60>, 'abort': <threading.Event object at 0x125589ae0>, 'log': <calibre.utils.logging.GUILog object at 0x125589c00>}

[Quoth]

IP address blacklisted by recipient

Not really a Calibre issue.

[theducks]

The keyword in that error was REFUSED.

You have to manage your KINDLE account to accept emailed from a sender (you)

This is not a Calibre issue.

[kovidgoyal]

You need to set up a email relay like gmx or hotmail https://manual.calibre-ebook.com/faq...-using-calibre

[ayjay3]

Sorry, but it is a Calibre problem.
It has always worked by sharing from Calibre. The email address used has been approved for years. Only has it stopped being accepted by Kindle for the last few weeks. It works fine if I email it myself or upload to Kindle, but not using Calibre as I always used to do.

[ayjay3]

Originally Posted by kovidgoyal

You need to set up a email relay like gmx or hotmail https://manual.calibre-ebook.com/faq...-using-calibre

Sorry, I have no idea what this means.

[DNSB]

Originally Posted by ayjay3

Sorry, but it is a Calibre problem.
It has always worked by sharing from Calibre. The email address used has been approved for years. Only has it stopped being accepted by Kindle for the last few weeks. It works fine if I email it myself or upload to Kindle, but not using Calibre as I always used to do.

Re-read your original post. Pay special attention to the line that reads:

OSError: Failed to send mail: SMTPRecipientsRefused({'XX@kindle.com': (550, b'5.7.1 IP address blacklisted by recipient')})

A quick search on a 550 5.71 error says:

550, "5.7. 1", The user or domain that you are sending to (or from) has a policy that prohibited the mail that you sent.

You are attempting to send directly to your Kindle email address. As mentioned by Kovid Goyal, you need to send using an email relay such as GMX or Hotmail/Outlook.com.

If you are interested, you may want to read up on SPF, DKIM and DMARC as security features for SMTP mail transfers. The implementation of those features has made using an email server with calibre pretty much a necessity.

As for setting up an email relay? Open calibre's Preferences => Sharing books by email and look at the email server box near the bottom.

[ayjay3]

Oh! I see, thank you.

It's just too complicated and I don't use or want to use Outlook or GMX email accounts. Are there any alternatives, such as iCloud?

If not, I'll just stop using Calibre to share books and just use my (Amazon authorised) email for now.

Thank you

[DNSB]

Originally Posted by ayjay3

Oh! I see, thank you.

It's just too complicated and I don't use or want to use Outlook or GMX email accounts. Are there any alternatives, such as iCloud?

If not, I'll just stop using Calibre to share books and just use my (Amazon authorised) email for now.

Thank you

You can set up other email accounts as long as they allow you to log in and use SMTP. Easier is to set it up and then use the test button.

[CathyA]

Originally Posted by ayjay3

... It's just too complicated and I don't use or want to use Outlook or GMX email accounts. Are there any alternatives, such as iCloud?...

Yes. Who's your normal email provider? Google something like "[your email provider name] smtp settings". Put that info in Calibre's Sharing books by email preferences screen, in the section for Email server. You can ignore the buttons for GMX and Outlook and put the correct info for your own email account there.

I use Gmail, but any other mail provider that accepts SMTP messages should also work fine.

[pcola]

i had this problem with gmail. here's how i fixed it:

calibre settings: sharing books by email: use the optional manually inputed server settings at the bottom left as follows

hostname: smtp.gmail.com
port: 465
username: [your name]@gmail.com
password: generate a mail application password here and use it, not your normal google/gmail password. this will fix the 2 factor authorization error that is the cause of this problem.
encryption: SSL
send test email

i have not yet changed the 5 min spam delay but i used to send several books at once from this same email so will probably change that in calibre tweaks

===
information for the application password setup for smtp mail was found in this article:https://kinsta.com/blog/gmail-smtp-server/

[gbm]

I would leave it alone, people have had their gmx relay banned.

bernie

Originally Posted by pcola

i have not yet changed the 5 min spam delay but i used to send several books at once from this same email so will probably change that in calibre tweaks

=

[pcola]

Is GMX the same as gmail?

tia

[jhowell]

Originally Posted by pcola

Is GMX the same as gmail?

tia

No. It is a different service.