Failure emailing to my Kindle

[hal@scogginsweb]

I just tried sending several books to my Kindle for the first time in quite a while, and got errors on all of them.

I'm currently running version 4.32, and I can't upgrade because I'm still running Windows 7, and the newer versions insist on Windows 10.

Any help would be appreciated. Here's the error detail:

calibre, version 4.23.0 (win32, embedded-python: True)
Failed to email book: Failed: Email Strong at the Broken Places to hscoggins@kindle.com

Starting job: Email Strong at the Broken Places to hscoggins@kindle.com
Waiting 1 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: (u'smtp.ehost.com', 587)
connect: (u'smtp.ehost.com', 587)

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 45, in run
File "site-packages\calibre\gui2\email.py", line 135, in sendmail
File "site-packages\calibre\utils\smtp.py", line 171, in sendmail
File "site-packages\polyglot\smtplib.py", line 67, in __init__
File "site-packages\calibre\utils\smtplib.py", line 275, in __init__
File "site-packages\calibre\utils\smtplib.py", line 339, in connect
File "site-packages\calibre\utils\smtplib.py", line 387, in getreply
SMTPServerDisconnected: Connection unexpectedly closed: [Errno 10054] An existing connection was forcibly closed by the remote host


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'smtp.ehost.com', 587)
connect: (u'smtp.ehost.com', 587)

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 45, in run
File "site-packages\calibre\gui2\email.py", line 135, in sendmail
File "site-packages\calibre\utils\smtp.py", line 171, in sendmail
File "site-packages\polyglot\smtplib.py", line 67, in __init__
File "site-packages\calibre\utils\smtplib.py", line 275, in __init__
File "site-packages\calibre\utils\smtplib.py", line 339, in connect
File "site-packages\calibre\utils\smtplib.py", line 387, in getreply
SMTPServerDisconnected: Connection unexpectedly closed: [Errno 10054] An existing connection was forcibly closed by the remote host

Job: "Email Strong at the Broken Places to hscoggins@kindle.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 102, in __call__
SMTPServerDisconnected: Connection unexpectedly closed: [Errno 10054] An existing connection was forcibly closed by the remote host

Called with args: (u'C:\\Users\\Hal\\AppData\\Local\\Temp\\calibre_r 1bg9l\\vbdhv7caltmpfmt.mobi', u'Strong at the Broken Places - Clayton Lindemuth.mobi', u'hscoggins@kindle.com', u'E-book: Strong at the Broken Places', u'Attached, you will find the e-book\n\nStrong at the Broken Places\n\tby Clayton Lindemuth\n\nin the MOBI format.') {u'notifications': <Queue.Queue instance at 0x0000000011485D88>, u'abort': <threading._Event object at 0x0000000011489048>, u'log': <calibre.utils.logging.GUILog object at 0x0000000011489188>}

[kovidgoyal]

That error indicates something is blocking calibre. Reboot in safe mode with networking and try it to confirm

[shopsis]

I'm having the same problem and am wondering if Google's two-level authentication is casing the problem. Here's the error message I get:

Starting job: Email TheAtlantic.com [Mon, 20 Dec 2021] to ipa.stout@free.kindle.com
connect: ('smtp.gmail.com', 465)
connect: ('smtp.gmail.com', 465)
reply: b'220 smtp.gmail.com ESMTP e15sm238366qtq.83 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP e15sm238366qtq.83 - gsmtp'
connect: b'smtp.gmail.com ESMTP e15sm238366qtq.83 - gsmtp'
send: 'ehlo DESKTOP-LQKFKS4.nycap.rr.com\r\n'
reply: b'250-smtp.gmail.com at your service, [2603:7080:306:665:20ef:3136:a694:ed3]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-CHUNKING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [2603:7080:306:665:20ef:3136:a694:ed3]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nCHUNKING\ nSMTPUTF8'
send: AUTH <censored>
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor e15sm238366qtq.83 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor e15sm238366qtq.83 - gsmtp'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'V2F0ZXI5OW1lbG9u\r\n'
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor e15sm238366qtq.83 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor e15sm238366qtq.83 - gsmtp'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor e15sm238366qtq.83 - gsmtp')


Retrying in 301 seconds...

Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: ('smtp.gmail.com', 465)
connect: ('smtp.gmail.com', 465)
reply: b'220 smtp.gmail.com ESMTP m1sm17428938qtk.34 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP m1sm17428938qtk.34 - gsmtp'
connect: b'smtp.gmail.com ESMTP m1sm17428938qtk.34 - gsmtp'
send: 'ehlo DESKTOP-LQKFKS4.nycap.rr.com\r\n'
reply: b'250-smtp.gmail.com at your service, [2603:7080:306:665:20ef:3136:a694:ed3]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-CHUNKING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [2603:7080:306:665:20ef:3136:a694:ed3]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nCHUNKING\ nSMTPUTF8'
send: AUTH <censored>
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor m1sm17428938qtk.34 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor m1sm17428938qtk.34 - gsmtp'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'V2F0ZXI5OW1lbG9u\r\n'
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor m1sm17428938qtk.34 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor m1sm17428938qtk.34 - gsmtp'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor m1sm17428938qtk.34 - gsmtp')

Job: "Email TheAtlantic.com [Mon, 20 Dec 2021] to ipa.stout@free.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 106, in __call__
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor m1sm17428938qtk.34 - gsmtp')

Called with args: ('C:\\Users\\Charlie\\AppData\\Local\\Temp\\calibr e_kyv57rgq\\bjrrgmfccaltmpfmt.MOBI', 'TheAtlantic.com [Mon, 20 Dec 2021] - calibre.MOBI', 'ipa.stout@free.kindle.com', 'E-book: TheAtlantic.com [Mon, 20 Dec 2021]', 'Attached, you will find the e-book\n\nTheAtlantic.com [Mon, 20 Dec 2021]\n\tby calibre\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x000002E10B17D160>, 'abort': <threading.Event object at 0x000002E10B17DC40>, 'log': <calibre.utils.logging.GUILog object at 0x000002E10B17D7C0>}

[DNSB]

Looking at the error message you received:

smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor m1sm17428938qtk.34 - gsmtp')

you have Gmail set to require 2FA for your computer. You should be able to create an application specific password for calibre. If you click on the link in the error message ( https://support.google.com/mail/?p=InvalidSecondFactor ), you will get some help.

[hal@scogginsweb]

Originally Posted by DNSB

Looking at the error message you received:

smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor m1sm17428938qtk.34 - gsmtp')

you have Gmail set to require 2FA for your computer. You should be able to create an application specific password for calibre. If you click on the link in the error message ( https://support.google.com/mail/?p=InvalidSecondFactor ), you will get some help.

I'm not using Gmail, so I'm not sure how that relates. But regardless, I'm going to close this thread, as it seems that the problem at the time had nothing to do with Calibre, but was a general email problem.

[shopsis]

Thanks. The App password solved the problem.

[DNSB]

Originally Posted by hal@scogginsweb

I'm not using Gmail, so I'm not sure how that relates. But regardless, I'm going to close this thread, as it seems that the problem at the time had nothing to do with Calibre, but was a general email problem.

Out of curiosity, which Google mail program are you using considering that you are connecting to Google's SMTP email server?

[jmurphy]

Originally Posted by DNSB

Out of curiosity, which Google mail program are you using considering that you are connecting to Google's SMTP email server?

He isn't. You replied to two different posts. The OP had an email problem of some sort, but the post with the err msg that you quoted was from someone else.

[DNSB]

True. I didn't read back in the thread and has assumed that the poster was the author of the message I had responded to which was @shopsis. My apologies to @hal@scogginsweb for not having done so.

[Freedomland]

I've had the same issue for a few weeks. I would convert an epub to mobi in Calibre using connect/share...and I would get the similar error. It started with v5.33.2, but honestly I don't think it's Calibre, I went to an older version and the error is still there. Instead I open the File Location, and right click (running W10) and use the Send-To-Kindle link.. but I can only do one at a time. A real pain if I want to send 9 books!! I have a feeling it's not Calibre nor Amazon, but a Google issue. Here's my error message:

Spoiler:

Starting job: Email The King In Yellow to freedomlandmini_mz3MI3@kindle.com
connect: ('smtp.gmail.com', 587)
connect: to ('smtp.gmail.com', 587) None
reply: b'220 smtp.gmail.com ESMTP k1sm13254113qkh.53 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP k1sm13254113qkh.53 - gsmtp'
connect: b'smtp.gmail.com ESMTP k1sm13254113qkh.53 - gsmtp'
send: 'ehlo Florida.home\r\n'
reply: b'250-smtp.gmail.com at your service, [67.86.61.76]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [67.86.61.76]\nSIZE 35882577\n8BITMIME\nSTARTTLS\nENHANCEDSTATUSCODES\ nPIPELINING\nSMTPUTF8'
send: 'STARTTLS\r\n'
reply: b'220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: b'2.0.0 Ready to start TLS'
send: 'ehlo Florida.home\r\n'
reply: b'250-smtp.gmail.com at your service, [67.86.61.76]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [67.86.61.76]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nSMTPUTF8'
send: AUTH <censored>
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k1sm13254113qkh.53 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k1sm13254113qkh.53 - gsmtp'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'TGl6YUphbmUxMjM=\r\n'
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k1sm13254113qkh.53 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k1sm13254113qkh.53 - gsmtp'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k1sm13254113qkh.53 - gsmtp')


Retrying in 15 seconds...

Waiting 15 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: ('smtp.gmail.com', 587)
connect: to ('smtp.gmail.com', 587) None
reply: b'220 smtp.gmail.com ESMTP w13sm14947654qko.20 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP w13sm14947654qko.20 - gsmtp'
connect: b'smtp.gmail.com ESMTP w13sm14947654qko.20 - gsmtp'
send: 'ehlo Florida.home\r\n'
reply: b'250-smtp.gmail.com at your service, [67.86.61.76]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [67.86.61.76]\nSIZE 35882577\n8BITMIME\nSTARTTLS\nENHANCEDSTATUSCODES\ nPIPELINING\nSMTPUTF8'
send: 'STARTTLS\r\n'
reply: b'220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: b'2.0.0 Ready to start TLS'
send: 'ehlo Florida.home\r\n'
reply: b'250-smtp.gmail.com at your service, [67.86.61.76]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [67.86.61.76]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nSMTPUTF8'
send: AUTH <censored>
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor w13sm14947654qko.20 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor w13sm14947654qko.20 - gsmtp'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'TGl6YUphbmUxMjM=\r\n'
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor w13sm14947654qko.20 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor w13sm14947654qko.20 - gsmtp'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor w13sm14947654qko.20 - gsmtp')

Job: "Email The King In Yellow to freedomlandmini_mz3MI3@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 106, in __call__
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor w13sm14947654qko.20 - gsmtp')

Called with args: ('C:\\Users\\jerry@adele_2\\AppData\\Local\\Temp\\ calibre_4itl6x9n\\vh4uyamccaltmpfmt.mobi', 'The King In Yellow - Robert W. Chambers.mobi', 'freedomlandmini_mz3MI3@kindle.com', 'CONVERT', 'Attached, you will find the e-book\n\nThe King In Yellow\n\tby Robert W. Chambers\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x0000021012C7E670>, 'abort': <threading.Event object at 0x0000021009167310>, 'log': <calibre.utils.logging.GUILog object at 0x0000021009167190>}

Any thoughts??? None of my settings have changed..and sending items to Amazon and the new PW 11th Gen have been great..until a few weeks ago. I would appreciate any help.

[aborel]

Originally Posted by Freedomland

Job: "Email The King In Yellow to freedomlandmini_mz3MI3@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 106, in __call__
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor w13sm14947654qko.20 - gsmtp')

Called with args: ('C:\\Users\\jerry@adele_2\\AppData\\Local\\Temp\\ calibre_4itl6x9n\\vh4uyamccaltmpfmt.mobi', 'The King In Yellow - Robert W. Chambers.mobi', 'freedomlandmini_mz3MI3@kindle.com', 'CONVERT', 'Attached, you will find the e-book\n\nThe King In Yellow\n\tby Robert W. Chambers\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x0000021012C7E670>, 'abort': <threading.Event object at 0x0000021009167310>, 'log': <calibre.utils.logging.GUILog object at 0x0000021009167190>}




Any thoughts??? None of my settings have changed..and sending items to Amazon and the new PW 11th Gen have been great..until a few weeks ago. I would appreciate any help.

You need to create a specific password in your Gmail account for the applications that Google doesn't trust (i.e. most non-Google applications, including of course calibre). See this page for more info: https://support.google.com/accounts/...idSecondFactor

[DNSB]

Looking at the error message you received from Google (which is pretty much identical to the error message in @shopsis' in message #3 in this thread):

reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor w13sm14947654qko.20 - gsmtp\r\n'

Have you tried setting an application specific password? The link in the error message indicates that that is required. Follow the link to Sign in with App Passwords in your error log or click on the link in this message.

[Freedomland]

Originally Posted by aborel

You need to create a specific password in your Gmail account for the applications that Google doesn't trust (i.e. most non-Google applications, including of course calibre). See this page for more info:

Spoiler:

https://support.google.com/accounts/...idSecondFactor

Spoiler:

I tried it.. and got it to generate the character pw for gmail.. and put that into Calibre and into Gmail..
Restarted Calibre.. and ZAP Still N.G.!!!

Starting job: Email Destination Void to freedomlandmini_mz3MI3@kindle.com
connect: ('smtp.gmail.com', 587)
connect: to ('smtp.gmail.com', 587) None
reply: b'220 smtp.gmail.com ESMTP c25sm16328736qkp.31 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP c25sm16328736qkp.31 - gsmtp'
connect: b'smtp.gmail.com ESMTP c25sm16328736qkp.31 - gsmtp'
send: 'ehlo Florida.home\r\n'
reply: b'250-smtp.gmail.com at your service, [67.86.61.76]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [67.86.61.76]\nSIZE 35882577\n8BITMIME\nSTARTTLS\nENHANCEDSTATUSCODES\ nPIPELINING\nSMTPUTF8'
send: 'STARTTLS\r\n'
reply: b'220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: b'2.0.0 Ready to start TLS'
send: 'ehlo Florida.home\r\n'
reply: b'250-smtp.gmail.com at your service, [67.86.61.76]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [67.86.61.76]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nSMTPUTF8'
send: AUTH <censored>
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor c25sm16328736qkp.31 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor c25sm16328736qkp.31 - gsmtp'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'enVsam93a2NmbXZveG11ag==\r\n'
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor c25sm16328736qkp.31 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor c25sm16328736qkp.31 - gsmtp'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor c25sm16328736qkp.31 - gsmtp')


Retrying in 15 seconds...

Waiting 15 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: ('smtp.gmail.com', 587)
connect: to ('smtp.gmail.com', 587) None
reply: b'220 smtp.gmail.com ESMTP k8sm15594620qko.130 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP k8sm15594620qko.130 - gsmtp'
connect: b'smtp.gmail.com ESMTP k8sm15594620qko.130 - gsmtp'
send: 'ehlo Florida.home\r\n'
reply: b'250-smtp.gmail.com at your service, [67.86.61.76]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [67.86.61.76]\nSIZE 35882577\n8BITMIME\nSTARTTLS\nENHANCEDSTATUSCODES\ nPIPELINING\nSMTPUTF8'
send: 'STARTTLS\r\n'
reply: b'220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: b'2.0.0 Ready to start TLS'
send: 'ehlo Florida.home\r\n'
reply: b'250-smtp.gmail.com at your service, [67.86.61.76]\r\n'
reply: b'250-SIZE 35882577\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [67.86.61.76]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nSMTPUTF8'
send: AUTH <censored>
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k8sm15594620qko.130 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k8sm15594620qko.130 - gsmtp'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'enVsam93a2NmbXZveG11ag==\r\n'
reply: b'534-5.7.9 Application-specific password required. Learn more at\r\n'
reply: b'534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k8sm15594620qko.130 - gsmtp\r\n'
reply: retcode (534); Msg: b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k8sm15594620qko.130 - gsmtp'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k8sm15594620qko.130 - gsmtp')

Job: "Email Destination Void to freedomlandmini_mz3MI3@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 106, in __call__
File "calibre\gui2\email.py", line 49, in run
File "calibre\gui2\email.py", line 133, in sendmail
File "calibre\utils\smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (534, b'5.7.9 Application-specific password required. Learn more at\n5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor k8sm15594620qko.130 - gsmtp')

Called with args: ('C:\\Users\\jerry@adele_2\\AppData\\Local\\Temp\\ calibre_qko7vz4s\\zw_6zedzcaltmpfmt.mobi', 'Destination Void - Frank Herbert.mobi', 'freedomlandmini_mz3MI3@kindle.com', 'CONVERT', 'Attached, you will find the e-book\n\nDestination Void\n\tby Frank Herbert\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x0000020A2C63F4C0>, 'abort': <threading.Event object at 0x0000020A2C626EE0>, 'log': <calibre.utils.logging.GUILog object at 0x0000020A2C626760>}

Anything else to try?? Maybe turn off 2 step verification??

[Freedomland]

I turned off 2-Step Verification and everything now works again. I had a feeling it was Google... Damn

[hal@scogginsweb]

I'm now having problems emailing a book again, and this time I confirmed that my email is working just fine outside of Calibre. Also, the error is different.

Here's the error I'm getting now. Please let me know what I need to do. Thanks.

calibre, version 5.36.0 (win32, embedded-python: True)
Failed to email book: Failed: Email Two Hours Ago to hscoggins@kindle.com

Starting job: Email Two Hours Ago to hscoggins@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: TimeoutError(10060, 'A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond', None, 10060, None)


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: TimeoutError(10060, 'A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond', None, 10060, None)

Job: "Email Two Hours Ago to hscoggins@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: TimeoutError(10060, 'A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond', None, 10060, None)

Called with args: ('C:\\Users\\HALSCO~1\\AppData\\Local\\Temp\\calib re_0lr5mxu0\\ehdsy8vhcaltmpfmt.mobi', 'Two Hours Ago - Joe Vasicek.mobi', 'hscoggins@kindle.com', 'E-book: Two Hours Ago', 'Attached, you will find the e-book\n\nTwo Hours Ago\n\tby Joe Vasicek\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x0FF86478>, 'abort': <threading.Event object at 0x0FF863D0>, 'log': <calibre.utils.logging.GUILog object at 0x0FF866E8>}