What am I doing wrong?

Booksters586 · 07-25-2022, 05:19 PM

I haven't been able to send documents to my email in a few weeks. However, I can manually send to device if it is connected. I haven't changed anything so i don't know why I get this error...

Code:

connect: to ('smtp.gmail.com', 587) None 
reply: b'220 smtp.gmail.com ESMTP br13-20020a05622a1e0d00b0031ea2328edcsm7798063qtb.82 - gsmtp\r\n' 
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP br13-20020a05622a1e0d00b0031ea2328edcsm7798063qtb.82 - gsmtp' 
connect: b'smtp.gmail.com ESMTP br13-20020a05622a1e0d00b0031ea2328edcsm7798063qtb.82 - gsmtp' 
send: 'ehlo LAPTOP-J0O49DD7.hsd1.mi.comcast.net\r\n' 
reply: b'250-smtp.gmail.com at your service, [2601:40c:8200:74c0:c17a:a628:3097:18f9]\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-CHUNKING\r\n' 
reply: b'250 SMTPUTF8\r\n' 
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [2601:40c:8200:74c0:c17a:a628:3097:18f9]\nSIZE 35882577\n8BITMIME\nSTARTTLS\nENHANCEDSTATUSCODES\nPIPELINING\nCHUNKING\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 LAPTOP-J0O49DD7.hsd1.mi.comcast.net\r\n' 
reply: b'250-smtp.gmail.com at your service, [2601:40c:8200:74c0:c17a:a628:3097:18f9]\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, [2601:40c:8200:74c0:c17a:a628:3097:18f9]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nCHUNKING\nSMTPUTF8' 
send: AUTH <censored> 
reply: b'535-5.7.8 Username and Password not accepted. Learn more at\r\n' 
reply: b'535 5.7.8  https://support.google.com/mail/?p=BadCredentials br13-20020a05622a1e0d00b0031ea2328edcsm7798063qtb.82 - gsmtp\r\n' 
reply: retcode (535); Msg: b'5.7.8 Username and Password not accepted. Learn more at\n5.7.8  https://support.google.com/mail/?p=BadCredentials br13-20020a05622a1e0d00b0031ea2328edcsm7798063qtb.82 - gsmtp' 
send: AUTH <censored> 
reply: b'334 UGFzc3dvcmQ6\r\n' 
reply: retcode (334); Msg: b'UGFzc3dvcmQ6' 
send: 'ISFTaGViYXQ5MyE/\r\n' 
reply: b'535-5.7.8 Username and Password not accepted. Learn more at\r\n' 
reply: b'535 5.7.8  https://support.google.com/mail/?p=BadCredentials br13-20020a05622a1e0d00b0031ea2328edcsm7798063qtb.82 - gsmtp\r\n' 
reply: retcode (535); Msg: b'5.7.8 Username and Password not accepted. Learn more at\n5.7.8  https://support.google.com/mail/?p=BadCredentials br13-20020a05622a1e0d00b0031ea2328edcsm7798063qtb.82 - gsmtp' 

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 180, in sendmail
  File "smtplib.py", line 750, in login
  File "smtplib.py", line 739, in login
  File "smtplib.py", line 662, in auth
smtplib.SMTPAuthenticationError: (535, b'5.7.8 Username and Password not accepted. Learn more at\n5.7.8  https://support.google.com/mail/?p=BadCredentials br13-20020a05622a1e0d00b0031ea2328edcsm7798063qtb.82 - 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: to ('smtp.gmail.com', 587) None 
reply: b'220 smtp.gmail.com ESMTP s9-20020a05620a29c900b006b5e3ca6400sm10150096qkp.103 - gsmtp\r\n' 
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP s9-20020a05620a29c900b006b5e3ca6400sm10150096qkp.103 - gsmtp' 
connect: b'smtp.gmail.com ESMTP s9-20020a05620a29c900b006b5e3ca6400sm10150096qkp.103 - gsmtp' 
send: 'ehlo LAPTOP-J0O49DD7.hsd1.mi.comcast.net\r\n' 
reply: b'250-smtp.gmail.com at your service, [2601:40c:8200:74c0:c17a:a628:3097:18f9]\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-CHUNKING\r\n' 
reply: b'250 SMTPUTF8\r\n' 
reply: retcode (250); Msg: b'smtp.gmail.com at your service, [2601:40c:8200:74c0:c17a:a628:3097:18f9]\nSIZE 35882577\n8BITMIME\nSTARTTLS\nENHANCEDSTATUSCODES\nPIPELINING\nCHUNKING\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 LAPTOP-J0O49DD7.hsd1.mi.comcast.net\r\n' 
reply: b'250-smtp.gmail.com at your service, [2601:40c:8200:74c0:c17a:a628:3097:18f9]\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, [2601:40c:8200:74c0:c17a:a628:3097:18f9]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nCHUNKING\nSMTPUTF8' 
send: AUTH <censored> 
reply: b'535-5.7.8 Username and Password not accepted. Learn more at\r\n' 
reply: b'535 5.7.8  https://support.google.com/mail/?p=BadCredentials s9-20020a05620a29c900b006b5e3ca6400sm10150096qkp.103 - gsmtp\r\n' 
reply: retcode (535); Msg: b'5.7.8 Username and Password not accepted. Learn more at\n5.7.8  https://support.google.com/mail/?p=BadCredentials s9-20020a05620a29c900b006b5e3ca6400sm10150096qkp.103 - gsmtp' 
send: AUTH <censored> 
reply: b'334 UGFzc3dvcmQ6\r\n' 
reply: retcode (334); Msg: b'UGFzc3dvcmQ6' 
send: 'ISFTaGViYXQ5MyE/\r\n' 
reply: b'535-5.7.8 Username and Password not accepted. Learn more at\r\n' 
reply: b'535 5.7.8  https://support.google.com/mail/?p=BadCredentials s9-20020a05620a29c900b006b5e3ca6400sm10150096qkp.103 - gsmtp\r\n' 
reply: retcode (535); Msg: b'5.7.8 Username and Password not accepted. Learn more at\n5.7.8  https://support.google.com/mail/?p=BadCredentials s9-20020a05620a29c900b006b5e3ca6400sm10150096qkp.103 - gsmtp' 

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 180, in sendmail
  File "smtplib.py", line 750, in login
  File "smtplib.py", line 739, in login
  File "smtplib.py", line 662, in auth
smtplib.SMTPAuthenticationError: (535, b'5.7.8 Username and Password not accepted. Learn more at\n5.7.8  https://support.google.com/mail/?p=BadCredentials s9-20020a05620a29c900b006b5e3ca6400sm10150096qkp.103 - gsmtp')

JSWolf · 07-25-2022, 05:36 PM

You have an error with your username and/or password. Try entering them again.

Booksters586 · 07-25-2022, 06:06 PM

Quote:

Originally Posted by JSWolf

You have an error with your username and/or password. Try entering them again.

I did and it's still telling me the same thing.

shamanNS · 07-25-2022, 08:41 PM

Maybe / probably Google has recently enabled 2FA on your account?

Try creating an "app password" and use that in Calibre's Send by email settings instead of your regular Gmail account password.

https://myaccount.google.com/apppasswords

Booksters586 · 07-25-2022, 09:31 PM

Quote:

Originally Posted by shamanNS

Maybe / probably Google has recently enabled 2FA on your account?

Try creating an "app password" and use that in Calibre's Send by email settings instead of your regular Gmail account password.

https://myaccount.google.com/apppasswords

I tried to follow that link and I received this

"The setting you are looking for is not available for your account."

I don't get it. I have been using Calibre for years and then all of a sudden it just stopped letting me send anything to my Kindle.

CathyA · 07-25-2022, 11:05 PM

You need to use an app password now. Google has made some changes and Gmail no longer accepts messages from "less secure apps", which used to work with Calibre.

Here are the instructions for enabling app passwords in your gmail account. https://support.google.com/mail/answer/185833

Note that you must turn on 2-step verification first. If you are unable to turn it on, then you may need to create a separate gmail address for use with Calibre.

Quoth · 07-26-2022, 09:02 AM

Google's so called "security" for so called "less secure apps" is simply a privacy theft.
I use other SMTPs.
I forward all email in all my gmail accounts to various non-google email accounts.
In over 30 years of email, I've never had it compromised. Stupid organisations have given away email addresses and one ISP exposed their user database. None of that is mitgated by google's abusive approach to you accessing your google email account. Using web mail is less secure than traditional POP3 + SMTP.

innocenat · 07-27-2022, 06:26 AM

Quote:

Originally Posted by Quoth

Google's so called "security" for so called "less secure apps" is simply a privacy theft.
I use other SMTPs.
I forward all email in all my gmail accounts to various non-google email accounts.
In over 30 years of email, I've never had it compromised. Stupid organisations have given away email addresses and one ISP exposed their user database. None of that is mitgated by google's abusive approach to you accessing your google email account. Using web mail is less secure than traditional POP3 + SMTP.

This is the first time I have even seen two-factor authentication and application passwords being called "privacy theft".

NullNix · 07-27-2022, 06:46 AM

Quote:

Originally Posted by innocenat

This is the first time I have even seen two-factor authentication and application passwords being called "privacy theft".

Yeah. The xoauth2 terms and conditions being promulgated by some providers (notably MS) sound much more like actual theft though: they reserve the right to ban you for using clients they haven't "approved", and to be "approved" clients need an alleged "security review" that costs a perfectly reasonable not at all suspiciously-round-numbered $100,000. And after it gets its "review" they might decide at any time that it needs another one, at your cost, oh that's another $100k. All this when a decently-designed protocol (like the one they're using) won't allow a malicious client to pose a threat to the server anyway!

More obvious anticompetitive "use our clients or pay our extortion fees" tactics to try to shut down one of the last remaining bastions of open protocols and hackable clients on the Internet I have never seen.

Quoth · 07-27-2022, 08:15 AM

Quote:

Originally Posted by innocenat

This is the first time I have even seen two-factor authentication and application passwords being called "privacy theft".

You can't easily use a different one for different Google accounts. You also have to give Google extra information, at least your phone number of a mobile. There isn't really any issue using SMTP & POP3 from anything other than public Wifi, which is insecure anyway using Oauth. The only security solution for Public WiFi is to use a VPN to a server/application to your home or office.

If you use a decent different password for everything the Google mandated 2FA isn't needed. Also mysteriously it's NOT needed for Google's mail client on Android nor on any browser used to access Google Web mail. It's a typical cynical Google/Alphabet internet land grab/privacy grab. If you use someone else's SMTP you can still send emails with gmail as from/replyto and to any gmail account. You can still setup your gmail via web, without any 2FA, to forward all email to a non-Google IMAP or POP3 account.

It's 10% security and 90% scam, approximately.

Also email by default on Android is just a Google client to a Google server. The details you put in are stored on a Google server and all the email in and out goes via Google! You can install a true 3rd party email client such as K9 email (free) on Android and then Google isn't the man in the middle. They are hypocrites!

Do you use SMS on an Android phone? You might want to install Signal as the default for SMS. Read up on how Android default SMS (Messages) works!

NullNix · 07-27-2022, 10:25 AM

Quote:

Originally Posted by Quoth

If you use a decent different password for everything the Google mandated 2FA isn't needed. Also mysteriously it's NOT needed for Google's mail client on Android nor on any browser used to access Google Web mail.

That's not true. You need to 2FA-authenticate at least once when you sign into your Google account, which necessarily happens before accessing your mail via either of those routes. (However, on Android let alone iPhones U2F stuff is still rather embryonic and many U2F tokens only talk USB and not all phones can handle that, so it's possible it was skipped there for a long time simply to avoid locking people out of their accounts completely -- but if it is, it's skipped for any logins to your Google account on there, not just for "Google's client".)

Quoth · 07-27-2022, 11:30 AM

Quote:

Originally Posted by NullNix

That's not true. You need to 2FA-authenticate at least once when you sign into your Google account, which necessarily happens before accessing your mail via either of those routes.

If you have not signed up to 2FA, then gmail still works on Web interface and Android phone. They make an exception for themselves.

shalym · 07-28-2022, 04:54 PM

Quote:

Originally Posted by Quoth

If you have not signed up to 2FA, then gmail still works on Web interface and Android phone. They make an exception for themselves.

I haven't signed up for 2fA with any of my google accounts, and I use all 3 of them with Thunderbird on my PC and Blue Mail on my phone. I haven't had an issue with either of these.

Shari

Quoth · 07-29-2022, 07:19 AM

Certainly on my gmail Thunderbird can no longer log in. I had all the correct extra settings (which shouldn't be needed, a deliberate attempt by google to make you use Webmail or google clients).
Google warned this would happen.
Thunderbird does support the required extra Google security, which requires at least a working mobile number to implement.

They are an advertising sales company. Every policy is driven by that.

JSWolf · 07-29-2022, 08:33 AM

Quote:

Originally Posted by Quoth

Certainly on my gmail Thunderbird can no longer log in. I had all the correct extra settings (which shouldn't be needed, a deliberate attempt by google to make you use Webmail or google clients).
Google warned this would happen.
Thunderbird does support the required extra Google security, which requires at least a working mobile number to implement.

They are an advertising sales company. Every policy is driven by that.

Thunderbird is working well with Gmail.

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07-25-2022, 05:36 PM	#2
JSWolf Resident Curmudgeon Posts: 73,897 Karma: 128597114 Join Date: Nov 2006 Location: Roslindale, Massachusetts Device: Kobo Libra 2, Kobo Aura H2O, PRS-650, PRS-T1, nook STR, PW3	You have an error with your username and/or password. Try entering them again.

07-25-2022, 08:41 PM	#4
shamanNS Guru Posts: 885 Karma: 10113994 Join Date: Feb 2010 Location: Serbia Device: Kindle PW5 [bricked], Kindle PW1	Maybe / probably Google has recently enabled 2FA on your account? Try creating an "app password" and use that in Calibre's Send by email settings instead of your regular Gmail account password. https://myaccount.google.com/apppasswords

07-25-2022, 11:05 PM	#6
CathyA Zealot Posts: 100 Karma: 903052 Join Date: Jun 2017 Device: Kindle Paperwhite	You need to use an app password now. Google has made some changes and Gmail no longer accepts messages from "less secure apps", which used to work with Calibre. Here are the instructions for enabling app passwords in your gmail account. https://support.google.com/mail/answer/185833 Note that you must turn on 2-step verification first. If you are unable to turn it on, then you may need to create a separate gmail address for use with Calibre.

07-26-2022, 09:02 AM	#7
Quoth the rook, bossing Never. Posts: 11,096 Karma: 85874891 Join Date: Jun 2017 Location: Ireland Device: All 4 Kinds: epub eink, Kindle, android eink, NxtPaper11	Google's so called "security" for so called "less secure apps" is simply a privacy theft. I use other SMTPs. I forward all email in all my gmail accounts to various non-google email accounts. In over 30 years of email, I've never had it compromised. Stupid organisations have given away email addresses and one ISP exposed their user database. None of that is mitgated by google's abusive approach to you accessing your google email account. Using web mail is less secure than traditional POP3 + SMTP.

07-29-2022, 07:19 AM	#14
Quoth the rook, bossing Never. Posts: 11,096 Karma: 85874891 Join Date: Jun 2017 Location: Ireland Device: All 4 Kinds: epub eink, Kindle, android eink, NxtPaper11	Certainly on my gmail Thunderbird can no longer log in. I had all the correct extra settings (which shouldn't be needed, a deliberate attempt by google to make you use Webmail or google clients). Google warned this would happen. Thunderbird does support the required extra Google security, which requires at least a working mobile number to implement. They are an advertising sales company. Every policy is driven by that.

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