[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.