[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??