Can't email books to Kindle with Gmail

[Teeny]

I got a Fire HD 10 (7th gen) and I tried to email books to Kindle from my gmail as always but I'm getting the error below. I don't know if the problem existed before I got the new Kindle or not 'cos I hadn't emailed books in awhile.

Starting job: Email Diamond in the Rough: Four Kings Security Book Four to chrisazaria@kindle.com 
connect: (u'smtp.gmail.com', 465) 
connect: (u'smtp.gmail.com', 465) 
reply: '220 smtp.gmail.com ESMTP h137sm3549035wmg.41 - gsmtp\r\n' 
reply: retcode (220); Msg: smtp.gmail.com ESMTP h137sm3549035wmg.41 - gsmtp 
connect: smtp.gmail.com ESMTP h137sm3549035wmg.41 - gsmtp 
send: 'ehlo [192.168.43.63]\r\n' 
reply: '250-smtp.gmail.com at your service, [5.144.200.59]\r\n' 
reply: '250-SIZE 35882577\r\n' 
reply: '250-8BITMIME\r\n' 
reply: '250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n' 
reply: '250-ENHANCEDSTATUSCODES\r\n' 
reply: '250-PIPELINING\r\n' 
reply: '250-CHUNKING\r\n' 
reply: '250 SMTPUTF8\r\n' 
reply: retcode (250); Msg: smtp.gmail.com at your service, [5.144.200.59]
SIZE 35882577
8BITMIME
AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
ENHANCEDSTATUSCODES
PIPELINING
CHUNKING
SMTPUTF8 
send: AUTH <censored> 
reply: '534-5.7.9 Application-specific password required. Learn more at\r\n' 
reply: '534 5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor h137sm3549035wmg.41 - gsmtp\r\n' 
reply: retcode (534); Msg: 5.7.9 Application-specific password required. Learn more at
5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor h137sm3549035wmg.41 - gsmtp 

Sending failed...
 
Traceback (most recent call last):
  File "site-packages\calibre\gui2\email.py", line 44, in run
  File "site-packages\calibre\gui2\email.py", line 134, in sendmail
  File "site-packages\calibre\utils\smtp.py", line 158, in sendmail
  File "site-packages\calibre\utils\smtplib.py", line 648, in login
SMTPAuthenticationError: (534, '5.7.9 Application-specific password required. Learn more at\n5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor h137sm3549035wmg.41 - gsmtp')

I'm attaching my preferences. My calibre is the 3.31 and I can't update anytime soon 'cos I don't have internet. Also NO I don't want to use GMX or other email.

[gbm]

Originally Posted by Teeny

I got a Fire HD 10 (7th gen) and I tried to email books to Kindle from my gmail as always but I'm getting the error below. I don't know if the problem existed before I got the new Kindle or not 'cos I hadn't emailed books in awhile.

Starting job: Email Diamond in the Rough: Four Kings Security Book Four to chrisazaria@kindle.com 
connect: (u'smtp.gmail.com', 465) 
connect: (u'smtp.gmail.com', 465) 
reply: '220 smtp.gmail.com ESMTP h137sm3549035wmg.41 - gsmtp\r\n' 
reply: retcode (220); Msg: smtp.gmail.com ESMTP h137sm3549035wmg.41 - gsmtp 
connect: smtp.gmail.com ESMTP h137sm3549035wmg.41 - gsmtp 
send: 'ehlo [192.168.43.63]\r\n' 
reply: '250-smtp.gmail.com at your service, [5.144.200.59]\r\n' 
reply: '250-SIZE 35882577\r\n' 
reply: '250-8BITMIME\r\n' 
reply: '250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\r\n' 
reply: '250-ENHANCEDSTATUSCODES\r\n' 
reply: '250-PIPELINING\r\n' 
reply: '250-CHUNKING\r\n' 
reply: '250 SMTPUTF8\r\n' 
reply: retcode (250); Msg: smtp.gmail.com at your service, [5.144.200.59]
SIZE 35882577
8BITMIME
AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
ENHANCEDSTATUSCODES
PIPELINING
CHUNKING
SMTPUTF8 
send: AUTH <censored> 
reply: '534-5.7.9 Application-specific password required. Learn more at\r\n' 
reply: '534 5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor h137sm3549035wmg.41 - gsmtp\r\n' 
reply: retcode (534); Msg: 5.7.9 Application-specific password required. Learn more at
5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor h137sm3549035wmg.41 - gsmtp 

Sending failed...
 
Traceback (most recent call last):
  File "site-packages\calibre\gui2\email.py", line 44, in run
  File "site-packages\calibre\gui2\email.py", line 134, in sendmail
  File "site-packages\calibre\utils\smtp.py", line 158, in sendmail
  File "site-packages\calibre\utils\smtplib.py", line 648, in login
SMTPAuthenticationError: (534, '5.7.9 Application-specific password required. Learn more at\n5.7.9  https://support.google.com/mail/?p=InvalidSecondFactor h137sm3549035wmg.41 - gsmtp')

I'm attaching my preferences. My calibre is the 3.31 and I can't update anytime soon 'cos I don't have internet. Also NO I don't want to use GMX or other email.

How are you sendig email with out internet?

https://support.google.com/mail/answer/185833?hl=en

Sign in using App Passwords

An App password is a 16-digit passcode that gives an app or device permission to access your Google Account. If you use 2-Step-Verification and are seeing a “password incorrect” error when trying to access your Google Account, an App password may solve the problem. Most of the time, you’ll only have to enter an App password once per app or device, so don’t worry about memorizing it.

bernie