Calibre problem sending to email

[bllittle]

Thank you for the great work! I've been using Calibre a couple of days and really enjoy it. Now trying to set up email delivery but also encountering problem. I tried my gmail account first, but kept getting the unexpected close error so I set up a gmx account. After making the adjustment on their setting to allow automated emails, I now get this log in the email Test:
Traceback (most recent call last):
File "calibre\gui2\wizard\send_email.py", line 205, in test_email_settings
File "calibre\utils\smtp.py", line 189, in sendmail
File "smtplib.py", line 871, in sendmail
smtplib.SMTPSenderRefused: (501, b'Syntax error in parameters or arguments', 'wundermuse')


Log:

Spoiler:

connect: ('mail.gmx.com', 587)
connect: to ('mail.gmx.com', 587) None
reply: b'220 gmx.net (mrgmx104) Nemesis ESMTP Service ready\r\n'
reply: retcode (220); Msg: b'gmx.net (mrgmx104) Nemesis ESMTP Service ready'
connect: b'gmx.net (mrgmx104) Nemesis ESMTP Service ready'
send: 'ehlo DESKTOP-67KD7SR.Home\r\n'
reply: b'250-gmx.net Hello DESKTOP-67KD7SR.Home [174.29.209.209]\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-SIZE 69920427\r\n'
reply: b'250 STARTTLS\r\n'
reply: retcode (250); Msg: b'gmx.net Hello DESKTOP-67KD7SR.Home [174.29.209.209]\n8BITMIME\nSIZE 69920427\nSTARTTLS'
send: 'STARTTLS\r\n'
reply: b'220 OK\r\n'
reply: retcode (220); Msg: b'OK'
send: 'ehlo DESKTOP-67KD7SR.Home\r\n'
reply: b'250-gmx.net Hello DESKTOP-67KD7SR.Home [174.29.209.209]\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN\r\n'
reply: b'250 SIZE 69920427\r\n'
reply: retcode (250); Msg: b'gmx.net Hello DESKTOP-67KD7SR.Home [174.29.209.209]\n8BITMIME\nAUTH LOGIN PLAIN\nSIZE 69920427'
send: AUTH <censored>
reply: b'235 Authentication succeeded\r\n'
reply: retcode (235); Msg: b'Authentication succeeded'
send: 'mail FROM:<wundermuse> size=561\r\n'
reply: b'501 Syntax error in parameters or arguments\r\n'
reply: retcode (501); Msg: b'Syntax error in parameters or arguments'
send: 'rset\r\n'
reply: b'250 OK\r\n'
reply: retcode (250); Msg: b'OK'
send: 'quit\r\n'
reply: b'221 gmx.net Service closing transmission channel\r\n'
reply: retcode (221); Msg: b'gmx.net Service closing transmission channel'

Suggestions? I suspect it is something simple I am overlooking since I am new to this program.

[DNSB]

Originally Posted by bllittle

Suggestions? I suspect it is something simple I am overlooking since I am new to this program.

At a wild eyed guess, where does the wundermuse in the MAIL from: line come from?

[kovidgoyal]

you need to put your full email address not just wundermuse.

[bllittle]

Originally Posted by kovidgoyal

you need to put your full email address not just wundermuse.

Thank you! I suspected it must be something simple.

And thanks again for the great program. I originally downloaded it to create mobi files rather than pdfs but have found other uses for it -- love the news aggregator.

[LeahHodgese]

It's really great program, but most likely sending and configuring does not work because of the antivirus on the phone? I had a similar problem 4 years ago when I had an android phone. By default, I installed McAfee antivirus, and after that, the phone worked very poorly. Then the notifications did not come, and the launch of programs became slower. I do not know why to install antivirus programs at all if they cause so many problems. I have long since switched to Total protection on my PC. And in general, if I need to compare something, I usually use this site (askanydifference.com). I hope it will be useful for everyone)

[arialvetica]

I have a new laptop, Windows 10, fresh Calibre install. I configured my preferences as usual. Successful test email (within Preferences: Sharing books by email: Test email). Authenticates credentials. Fails to send book.

I uninstalled the McAfee software that came with my PC, and disabled the Windows Defender Firewall & Network Protection.

Spoiler:

Starting job: Email Dragons and Marshmallows to xxxxx@kindle.com
connect: ('mail.gmx.com', 587)
connect: to ('mail.gmx.com', 587) None
reply: b'220 gmx.net (mrgmx004) Nemesis ESMTP Service ready\r\n'
reply: retcode (220); Msg: b'gmx.net (mrgmx004) Nemesis ESMTP Service ready'
connect: b'gmx.net (mrgmx004) Nemesis ESMTP Service ready'
send: 'ehlo Freya.lan\r\n'
reply: b'250-gmx.net Hello Freya.lan [173.235.226.42]\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-SIZE 69920427\r\n'
reply: b'250 STARTTLS\r\n'
reply: retcode (250); Msg: b'gmx.net Hello Freya.lan [173.235.226.42]\n8BITMIME\nSIZE 69920427\nSTARTTLS'
send: 'STARTTLS\r\n'
reply: b'220 OK\r\n'
reply: retcode (220); Msg: b'OK'
send: 'ehlo Freya.lan\r\n'
reply: b'250-gmx.net Hello Freya.lan [173.235.226.42]\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN\r\n'
reply: b'250 SIZE 69920427\r\n'
reply: retcode (250); Msg: b'gmx.net Hello Freya.lan [173.235.226.42]\n8BITMIME\nAUTH LOGIN PLAIN\nSIZE 69920427'
send: AUTH
reply: b'235 Authentication succeeded\r\n'
reply: retcode (235); Msg: b'Authentication succeeded'
send: 'mail FROM: size=18865966\r\n'
reply: b'250 Requested mail action okay, completed\r\n'
reply: retcode (250); Msg: b'Requested mail action okay, completed'
send: 'rcpt TO:\r\n'
reply: b'250 OK\r\n'
reply: retcode (250); Msg: b'OK'
send: 'data\r\n'
reply: b'354 Start mail input; end with .\r\n'
reply: retcode (354); Msg: b'Start mail input; end with .'
data: (354, b'Start mail input; end with .')
send: b'Content-Type: multipart/mixed; boundary="===============0184457556=="\nMIME-Version: 1.0\nSubject:...
reply: b'501 Syntax error - line too long\r\n'
reply: retcode (501); Msg: b'Syntax error - line too long'
data: (501, b'Syntax error - line too long')
send: 'rset\r\n'
send: 'quit\r\n'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 191, in sendmail
File "smtplib.py", line 892, in sendmail
smtplib.SMTPDataError: (501, b'Syntax error - line too long')


Retrying in 301 seconds...

Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: ('mail.gmx.com', 587)
connect: to ('mail.gmx.com', 587) None
reply: b'220 gmx.net (mrgmx004) Nemesis ESMTP Service ready\r\n'
reply: retcode (220); Msg: b'gmx.net (mrgmx004) Nemesis ESMTP Service ready'
connect: b'gmx.net (mrgmx004) Nemesis ESMTP Service ready'
send: 'ehlo Freya.lan\r\n'
reply: b'250-gmx.net Hello Freya.lan [173.235.226.42]\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-SIZE 69920427\r\n'
reply: b'250 STARTTLS\r\n'
reply: retcode (250); Msg: b'gmx.net Hello Freya.lan [173.235.226.42]\n8BITMIME\nSIZE 69920427\nSTARTTLS'
send: 'STARTTLS\r\n'
reply: b'220 OK\r\n'
reply: retcode (220); Msg: b'OK'
send: 'ehlo Freya.lan\r\n'
reply: b'250-gmx.net Hello Freya.lan [173.235.226.42]\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN\r\n'
reply: b'250 SIZE 69920427\r\n'
reply: retcode (250); Msg: b'gmx.net Hello Freya.lan [173.235.226.42]\n8BITMIME\nAUTH LOGIN PLAIN\nSIZE 69920427'
send: AUTH
reply: b'235 Authentication succeeded\r\n'
reply: retcode (235); Msg: b'Authentication succeeded'
send: 'mail FROM: size=18865966\r\n'
reply: b'250 Requested mail action okay, completed\r\n'
reply: retcode (250); Msg: b'Requested mail action okay, completed'
send: 'rcpt TO:\r\n'
reply: b'250 OK\r\n'
reply: retcode (250); Msg: b'OK'
send: 'data\r\n'
reply: b'354 Start mail input; end with .\r\n'
reply: retcode (354); Msg: b'Start mail input; end with .'
data: (354, b'Start mail input; end with .')
send: b'Content-Type: multipart/mixed; boundary="===============0576450956=="\nMIME-Version: 1.0\nSubject:...
reply: b'501 Syntax error - line too long\r\n'
reply: retcode (501); Msg: b'Syntax error - line too long'
data: (501, b'Syntax error - line too long')
send: 'rset\r\n'
send: 'quit\r\n'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 191, in sendmail
File "smtplib.py", line 892, in sendmail
smtplib.SMTPDataError: (501, b'Syntax error - line too long')

Job: "Email Dragons and Marshmallows to xxxxx@kindle.com" failed with error:
Traceback (most recent call last):
File "calibre\gui2\threaded_jobs.py", line 83, in start_work
File "calibre\gui2\email.py", line 102, in __call__
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 191, in sendmail
File "smtplib.py", line 892, in sendmail
smtplib.SMTPDataError: (501, b'Syntax error - line too long')

Called with args: ('C:\\Users\\xxxxx\\AppData\\Local\\Temp\\calibre_ 4e855z9l\\xnkyb1tacaltmpfmt.mobi', 'Dragons and Marshmallows - Asia Citro.mobi', 'xxxxx@kindle.com', 'A book you will enjoy', 'Attached, you will find the e-book\n\nDragons and Marshmallows\n\tby Asia Citro\n\nin the MOBI format.\n\nAbout this book:\n\nWith magical animals, science, mystery, and adventure -- the brand new\nseries Zoey and Sassafras has something for everyone! Easy-to-read\nlanguage and illustrations on nearly every page make this series\nperfect for a wide range of ages. In the first book of this series,\nZoey discovers a glowing photo and learns an amazing secret. Injured\nmagical animals come to their backyard barn for help! When a sick baby\ndragon appears, it’s up to Zoey and Sassafras to figure out what’s\nwrong. Will they be able to help little Marshmallow before it’s too\nlate?') {'notifications': , 'abort': , 'log': }

[theducks]

Just confirming:
You did modify the log (xxxxx) to remove your Amazon kindle ID ??

IIRC the test really only checks the SENDability side
Please re-enable Defender, you should never run a connected PC 'bare' these days.

(If there were issues with Defender, there would be lots of posts here at MR. )

[kovidgoyal]

@arialvetica: this is a bug in the latest calibre release, you can either wait for the next release where it will be fixed or downgrade to the previous release https://github.com/kovidgoyal/calibr...8cd72721f1a877

[arialvetica]

Yes, I replaced my IDs with xxxxxx when pasting the log here. When I run the test email, the email successfully sends AND I successfully receive an email from Amazon on my amazon-registered email address:

Your message to xxxxxx@kindle.com, sent at 05:01 PM on Sat, Feb 27, 2021 GMT did not include any attached documents or image files.

I will re-enable Defender. Hopefully someone can interpret the log and tell me why emails can send, but books cannot.

Originally Posted by theducks

Just confirming:
You did modify the log (xxxxx) to remove your Amazon kindle ID ??

IIRC the test really only checks the SENDability side
Please re-enable Defender, you should never run a connected PC 'bare' these days.

(If there were issues with Defender, there would be lots of posts here at MR. )

[arialvetica]

Thank you!! I have installed previous version (5.11.0) and it worked in 6 seconds! Thank you so much for providing such stellar support on my #1 favorite software!

Originally Posted by kovidgoyal

@arialvetica: this is a bug in the latest calibre release, you can either wait for the next release where it will be fixed or downgrade to the previous release https://github.com/kovidgoyal/calibr...8cd72721f1a877

[theducks]

Originally Posted by arialvetica

Yes, I replaced my IDs with xxxxxx when pasting the log here. When I run the test email, the email successfully sends AND I successfully receive an email from Amazon on my amazon-registered email address:



I will re-enable Defender. Hopefully someone can interpret the log and tell me why emails can send, but books cannot.

Glad to hear BOTH answers. That means you are a careful WWW user and will have less issues than some folk

[fnd]

can anyone help please?

Spoiler:

Traceback (most recent call last):
File "calibre\gui2\wizard\send_email.py", line 205, in test_email_settings
File "calibre\utils\smtp.py", line 173, in sendmail
File "calibre\utils\smtp.py", line 153, in sendmail_direct
OSError: Failed to send mail: SMTPServerDisconnected('Connection unexpectedly closed')


Log:
Find mail exchanger for dalal.org.uk
connect: ('mx01.1and1.co.uk.', 25)
connect: to ('mx01.1and1.co.uk.', 25) None
reply: b'554-kundenserver.de (mxeue112) Nemesis ESMTP Service not available\r\n'
reply: b'554-No SMTP service\r\n'
reply: b'554-IP address is block listed.\r\n'
reply: b'554 For explanation visit https://www.ionos.com/help/index.php...1.103&c=bl\r\n'
reply: retcode (554); Msg: b'kundenserver.de (mxeue112) Nemesis ESMTP Service not available\nNo SMTP service\nIP address is block listed.\nFor explanation visit https://www.ionos.com/help/index.php...5.171.103&c=bl'
connect: b'kundenserver.de (mxeue112) Nemesis ESMTP Service not available\nNo SMTP service\nIP address is block listed.\nFor explanation visit https://www.ionos.com/help/index.php...5.171.103&c=bl'
send: 'ehlo [192.168.0.193]\r\n'
connect: ('mx00.1and1.co.uk.', 25)
connect: to ('mx00.1and1.co.uk.', 25) None
reply: b'554-kundenserver.de (mxeue010) Nemesis ESMTP Service not available\r\n'
reply: b'554-No SMTP service\r\n'
reply: b'554-IP address is block listed.\r\n'
reply: b'554 For explanation visit https://www.ionos.com/help/index.php...1.103&c=bl\r\n'
reply: retcode (554); Msg: b'kundenserver.de (mxeue010) Nemesis ESMTP Service not available\nNo SMTP service\nIP address is block listed.\nFor explanation visit https://www.ionos.com/help/index.php...5.171.103&c=bl'
connect: b'kundenserver.de (mxeue010) Nemesis ESMTP Service not available\nNo SMTP service\nIP address is block listed.\nFor explanation visit https://www.ionos.com/help/index.php...5.171.103&c=bl'
send: 'ehlo [192.168.0.193]\r\n'
Traceback (most recent call last):
File "calibre\utils\smtp.py", line 145, in sendmail_direct
File "smtplib.py", line 927, in send_message
File "smtplib.py", line 604, in ehlo_or_helo_if_needed
File "smtplib.py", line 445, in ehlo
File "smtplib.py", line 398, in getreply
smtplib.SMTPServerDisconnected: Connection unexpectedly closed

[theducks]

did you try and read the log for a clue?

block listed
(I think this means your IP range has been blacklisted as a baddie)

No SMTP service.
(where you are sending to/from has no basic mail service or your port setting is wrong for the mode set. Many have blocked the old port 110)

[kovidgoyal]

Follow the instructions:
https://manual.calibre-ebook.com/faq...-using-calibre

[DNSB]

Originally Posted by fnd

can anyone help please?

reply: b'554-No SMTP service\r\n'
reply: b'554-IP address is block listed.\r\n'
reply: b'554 For explanation visit https://www.ionos.com/help/index.php...1.103&c=bl\r\n'
reply: retcode (554); Msg: b'kundenserver.de (mxeue112) Nemesis ESMTP Service not available\nNo SMTP service\nIP address is block listed.\nFor explanation visit https://www.ionos.com/help/index.php...5.171.103&c=bl'

If you check the URL in your posted log and look at the various reasons for a 554 code, you will find this one for a blacklisted address:

554 IP address is blacklisted

Problem:

A delivery of your email was rejected due to a DNSBL entry of your IP.

Solution;

Contact IONOS to have an incorrect entry checked.

Basically, it is saying that your IP address has been marked as sending spam. If you open Blacklist Check and click on Check My IP Address, it should let you know which DNSBL list if any your IP address is found on.