Emailing from Calibre fails at times

[Klippy]

I like to email books to myself from Calibre so I can read on my computer at work. Every now and then it will send the email but more often than not if fails. Failed to Email box comes up. When I pull up details this is what I see.

Spoiler:

calibre, version 2.27.0 (win32, isfrozen: True)
Failed to email book: Failed: Email Playing Doctor to xxxxxxxxxxxx@gmail.com

Starting job: Email Playing Doctor to xxxxxxxxxxxxxxxx@gmail.com
connect: (u'mail.gmx.com', 465)
connect: (u'mail.gmx.com', 465)
reply: '220 gmx.com (mrgmx003) Nemesis ESMTP Service ready\r\n'
reply: retcode (220); Msg: gmx.com (mrgmx003) Nemesis ESMTP Service ready
connect: gmx.com (mrgmx003) Nemesis ESMTP Service ready
send: 'ehlo [192.168.0.101]\r\n'
reply: '250-gmx.com Hello [192.168.0.101] [68.114.151.96]\r\n'
reply: '250-SIZE 69920427\r\n'
reply: '250 AUTH LOGIN PLAIN\r\n'
reply: retcode (250); Msg: gmx.com Hello [192.168.0.101] [68.114.151.96]
SIZE 69920427
AUTH LOGIN PLAIN
send: AUTH <censored>
reply: '235 Authentication succeeded\r\n'
reply: retcode (235); Msg: Authentication succeeded
send: u'mail FROM:<xxxxxxxxxx@gmx.com> size=258518\r\n'
reply: '250 Requested mail action okay, completed\r\n'
reply: retcode (250); Msg: Requested mail action okay, completed
send: u'rcpt TO:<xxxxxxxxxxx@gmail.com>\r\n'
reply: '550-Requested action not taken: mailbox unavailable\r\n'
reply: '550 Failure sending mail. Try again later\r\n'
reply: retcode (550); Msg: Requested action not taken: mailbox unavailable
Failure sending mail. Try again later
send: 'rset\r\n'
reply: '250 OK\r\n'
reply: retcode (250); Msg: OK
send: 'quit\r\n'
reply: '221 gmx.com Service closing transmission channel\r\n'
reply: retcode (221); Msg: gmx.com Service closing transmission channel

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 43, in run
File "site-packages\calibre\gui2\email.py", line 124, in sendmail
File "site-packages\calibre\utils\smtp.py", line 138, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 737, in sendmail
SMTPRecipientsRefused: {u'xxxxxxx@gmail.com': (550, 'Requested action not taken: mailbox unavailable\nFailure sending mail. Try again later')}


Retrying in 1 seconds...

Waiting 1 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: (u'mail.gmx.com', 465)
connect: (u'mail.gmx.com', 465)
reply: '220 gmx.com (mrgmx003) Nemesis ESMTP Service ready\r\n'
reply: retcode (220); Msg: gmx.com (mrgmx003) Nemesis ESMTP Service ready
connect: gmx.com (mrgmx003) Nemesis ESMTP Service ready
send: 'ehlo [192.168.0.101]\r\n'
reply: '250-gmx.com Hello [192.168.0.101] [68.114.151.96]\r\n'
reply: '250-SIZE 69920427\r\n'
reply: '250 AUTH LOGIN PLAIN\r\n'
reply: retcode (250); Msg: gmx.com Hello [192.168.0.101] [68.114.151.96]
SIZE 69920427
AUTH LOGIN PLAIN
send: AUTH <censored>
reply: '235 Authentication succeeded\r\n'
reply: retcode (235); Msg: Authentication succeeded
send: u'mail FROM:<xxxxxxxx@gmx.com> size=258518\r\n'
reply: '250 Requested mail action okay, completed\r\n'
reply: retcode (250); Msg: Requested mail action okay, completed
send: u'rcpt TO:<xxxxxxxx@gmail.com>\r\n'
reply: '550-Requested action not taken: mailbox unavailable\r\n'
reply: '550 Failure sending mail. Try again later\r\n'
reply: retcode (550); Msg: Requested action not taken: mailbox unavailable
Failure sending mail. Try again later
send: 'rset\r\n'
reply: '250 OK\r\n'
reply: retcode (250); Msg: OK
send: 'quit\r\n'
reply: '221 gmx.com Service closing transmission channel\r\n'
reply: retcode (221); Msg: gmx.com Service closing transmission channel

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 43, in run
File "site-packages\calibre\gui2\email.py", line 124, in sendmail
File "site-packages\calibre\utils\smtp.py", line 138, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 737, in sendmail
SMTPRecipientsRefused: {u'candtstephens@gmail.com': (550, 'Requested action not taken: mailbox unavailable\nFailure sending mail. Try again later')}

Job: "Email Playing Doctor to xxxxxxxxxx@gmail.com" failed with error:
Traceback (most recent call last):
File "site-packages\calibre\gui2\threaded_jobs.py", line 83, in start_work
File "site-packages\calibre\gui2\email.py", line 98, in __call__
SMTPRecipientsRefused: {u'xxxxxxxx@gmail.com': (550, 'Requested action not taken: mailbox unavailable\nFailure sending mail. Try again later')}

Called with args: (u'C:\\Users\\KAYELI~1\\AppData\\Local\\Temp\\cali bre_mrhrb2\\gs06qgcaltmpfmt.EPUB', u'Playing Doctor - Jan Meredith.EPUB', u'xxxxx@gmail.com', u'E-book: Playing Doctor', u"Attached, you will find the e-book\n\nPlaying Doctor\n\tby Jan Meredith\n\nin the EPUB format.\n\nAbout this book:\n\nA Holt Medallion Winner - BEST FIRST BOOK and ROMANCE NOVELLA - Award\nof Merit. One night with a sexy stranger is just what the doctor\nordered... When a fellow RN predicts Beth Roberts will meet a tall,\nripped, and totally lick-o-licious stranger who will fulfill her\ndeepest desires, she laughs it off. Given her tragic love life, Beth\nhas no desire to become involved again. But who could have predicted\nthe doctor with the mischievous smile she meets at a wedding, or the\nchemistry sparking between them that threatens to break through her\ndefenses? Dr. Gabriel North spent two years blaming himself for his\nwife's death. Having finally battled through the guilt and overcome\nhis demons, he's ready to move on. When he meets a sexy nurse at his\nfriend's wedding, the attraction is swift and strong, and he wastes no\ntime in pressing his advantage. One night with the woman who makes him\nfeel alive again isn't enough, but gaining Beth's trust is going to\ntake more than seduction... Previously released on the Flaunt imprint\nin November 2013.") {u'log': <calibre.utils.logging.GUILog object at 0x181CD150>, u'abort': <threading._Event object at 0x181CD350>, u'notifications': <Queue.Queue instance at 0x233817D8>}

Does anyone have any suggestion on what I might try? Thanks in advance for your help. I have tried my best to review everything posted on the board but none of the questions are quite like mine.

[eschwartz]

Apparently there are many reports of GMX having reliability issues and going offline at times.

[BetterRed]

@Klippy - try pinging gmx.com, if it ain't there, try again tomorrow, and tomorrow, and ...

This has been happening in various locations since November last year. UnitedInternet.de and subsidiaries like gmx and sites hosted by 1&1 disappear from DNS's. If gmx is still down trying pinging zabkat.com - if its down too, then its the same problem.

Given it has been happening for 6 months I suggest using an alternative mail service, like maybe your ISP's, then at least, you'll have some leverage.

That's the problem with free - its the advertiser who has the leverage rather than the customer. The advertising costs are socialised to the people who buy the advertised products. This is known as free-market capitalism or communism by stealth.

BR

[eschwartz]

I just use GMail, and "Allow access for insecure apps", i.e. anything that uses POP3/IMAP instead of Google bespoke software.

[Klippy]

Not to be stupid but do I just type in the email I want to send it from ? Do I have to fill in anything in the mail server info??? I am sorry if that is a dumb question -- I just cannot get this figured out.

[eschwartz]

When you configure the email address you are sending from, you need to fill out certain info. The SMTP server used and port number.

e.g. for GMail:

hostname (SMTP server): ----- smtp.gmail.com
port: ----------------------- 587
username: ------------------- somebody@gmail.com

[DuncanWatson]

This happens to me after sending 5 books to my kindle via email. I strongly suspect it is an anti-spam measure.

[Klippy]

Another crazy question how do I know the port used ? And is the STMP just stmp.whateveremailserviceyouuse.com?

[Klippy]

I still cannot get this crazy thing to work. See below and see if anyone has any help.

Starting job: Email XXXXXXXXX to XXXXXXXXXXX@gmail.com
connect: (u'stmp.gmail.com', 587)
connect: (u'stmp.gmail.com', 587)

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 43, in run
File "site-packages\calibre\gui2\email.py", line 124, in sendmail
File "site-packages\calibre\utils\smtp.py", line 128, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 308, in connect
File "site-packages\calibre\utils\smtplib.py", line 784, in _get_socket
File "ssl.py", line 891, in wrap_socket
File "ssl.py", line 566, in __init__
File "ssl.py", line 788, in do_handshake
SSLError: [SSL: UNKNOWN_PROTOCOL] unknown protocol (_ssl.c:581)


Retrying in 301 seconds...

Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: (u'stmp.gmail.com', 587)
connect: (u'stmp.gmail.com', 587)

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 43, in run
File "site-packages\calibre\gui2\email.py", line 124, in sendmail
File "site-packages\calibre\utils\smtp.py", line 128, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 308, in connect
File "site-packages\calibre\utils\smtplib.py", line 784, in _get_socket
File "ssl.py", line 891, in wrap_socket
File "ssl.py", line 566, in __init__
File "ssl.py", line 788, in do_handshake
SSLError: [SSL: UNKNOWN_PROTOCOL] unknown protocol (_ssl.c:581)

Job: "Email XXXXXXX to XXXXXXXXX@gmail.com" failed with error:
Traceback (most recent call last):
File "site-packages\calibre\gui2\threaded_jobs.py", line 83, in start_work
File "site-packages\calibre\gui2\email.py", line 98, in __call__
SSLError: [SSL: UNKNOWN_PROTOCOL] unknown protocol (_ssl.c:581)



What in the world am I doing wrong???? I had this working on my old computer now nothing I try seems to work!

[theducks]

Originally Posted by Klippy

Another crazy question how do I know the port used ? And is the STMP just stmp.whateveremailserviceyouuse.com?

It is whatever your ISP (mail service) says to use. This would be the same as you enter in Outlook, Eudora , Thunderbird ...

All the CALIBRE settings have a counterpart in a standard mail program.


Note, your firewall may attempt to block rogue mailers. You need to tell it that caliber.exe is a good guy

[PeterT]

Do you actually have stmp specified and not SMTP?