Error sending an ebook to my kindle via email

[uncletoma]

1) i'm using a @gmail.com email, changed calibre setting with gmail setting
2) but, always, i've this error (cut and past)
3) yes, i've put (not only) this email adress to my kindle setting "Manage your content and devices -> preferences -> approved personal document email list" on Amazon site.

calibre, version 7.1.0 (win32, embedded-python: True)
Invio del libro tramite email non riuscito: Non riuscita: Invia tramite email Questione di vita e di cuore a uncletoma@kindle.com

Starting job: Invia tramite email Questione di vita e di cuore a uncletoma@kindle.com
Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: to ('smtp.gmail.com', 465) None

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 172, in sendmail
File "polyglot\smtplib.py", line 36, in __init__
File "smtplib.py", line 255, in __init__
File "smtplib.py", line 343, in connect
File "smtplib.py", line 405, in getreply
smtplib.SMTPServerDisconnected: Connection unexpectedly closed


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', 465) None

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 172, in sendmail
File "polyglot\smtplib.py", line 36, in __init__
File "smtplib.py", line 255, in __init__
File "smtplib.py", line 343, in connect
File "smtplib.py", line 405, in getreply
smtplib.SMTPServerDisconnected: Connection unexpectedly closed

Job: "Invia tramite email Questione di vita e di cuore a uncletoma@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 172, in sendmail
File "polyglot\smtplib.py", line 36, in __init__
File "smtplib.py", line 255, in __init__
File "smtplib.py", line 343, in connect
File "smtplib.py", line 405, in getreply
smtplib.SMTPServerDisconnected: Connection unexpectedly closed

Called with args: ('C:\\Users\\uncle\\AppData\\Local\\Temp\\calibre_ qfdv88c8\\8lbt11vycaltmpfmt.epub', 'Questione di vita e di cuore.epub', 'uncletoma@kindle.com', 'ZEjsaiSQUeJLUh6CeuQlk4', 'tdPA2g3E4QLXkHMnboTs5D') {'notifications': <queue.Queue object at 0x000001AF13F72FD0>, 'abort': <threading.Event at 0x1af13f72d10: unset>, 'log': <calibre.utils.logging.GUILog object at 0x000001AF13F72D50>}

[kovidgoyal]

Something on your computer is killing the connection, most likely an antivirus or firewall program.

[uncletoma]

Originally Posted by kovidgoyal

Something on your computer is killing the connection, most likely an antivirus or firewall program.

Thanks, but only AV and firewall that i've are both with Windows 10 (Microsoft Defender and Microsoft Firewall).
Maybe should be a door problem on firewall? And what kind of door i must open?
Thanks in advance

[kovidgoyal]

reboot in safe mode see if the problem still happens there.

[uncletoma]

Originally Posted by kovidgoyal

reboot in safe mode see if the problem still happens there.

Reboot PC or Calibre?
BTW i allowed Calibre on Firewall and now i've username/password problem *_*
PIC to my settings

calibre, version 7.1.0 (win32, embedded-python: True)
Invio del libro tramite email non riuscito: Non riuscita: Invia tramite email Questione di vita e di cuore a uncletoma@kindle.com

Starting job: Invia tramite email Questione di vita e di cuore a uncletoma@kindle.com
connect: ('smtp.gmail.com', 465)
connect: to ('smtp.gmail.com', 465) None
reply: b'220 smtp.gmail.com ESMTP w17-20020a05600c475100b004080f0376a0sm2241296wmo.42 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP w17-20020a05600c475100b004080f0376a0sm2241296wmo.42 - gsmtp'
connect: b'smtp.gmail.com ESMTP w17-20020a05600c475100b004080f0376a0sm2241296wmo.42 - gsmtp'
send: 'ehlo Peppiniello.fritz.box\r\n'
reply: b'250-smtp.gmail.com at your service, [151.16.237.53]\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, [151.16.237.53]\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 w17-20020a05600c475100b004080f0376a0sm2241296wmo.42 - 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 w17-20020a05600c475100b004080f0376a0sm2241296wmo.42 - gsmtp'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'MTBhZ29zdG8xOTYyKzI=\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 w17-20020a05600c475100b004080f0376a0sm2241296wmo.42 - 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 w17-20020a05600c475100b004080f0376a0sm2241296wmo.42 - 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 181, 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 w17-20020a05600c475100b004080f0376a0sm2241296wmo.42 - 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: to ('smtp.gmail.com', 465) None
reply: b'220 smtp.gmail.com ESMTP q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - gsmtp'
connect: b'smtp.gmail.com ESMTP q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - gsmtp'
send: 'ehlo Peppiniello.fritz.box\r\n'
reply: b'250-smtp.gmail.com at your service, [151.16.237.53]\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, [151.16.237.53]\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 q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - 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 q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - gsmtp'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'MTBhZ29zdG8xOTYyKzI=\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 q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - 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 q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - 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 181, 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 q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - gsmtp')

Job: "Invia tramite email Questione di vita e di cuore a uncletoma@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 181, 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 q7-20020a05600c46c700b0040b4110f548sm2296018wmo.23 - gsmtp')

Called with args: ('C:\\Users\\uncle\\AppData\\Local\\Temp\\calibre_ qfdv88c8\\fbrb1w9icaltmpfmt.epub', 'Questione di vita e di cuore.epub', 'uncletoma@kindle.com', 'QLzoFojkmB6HQPymevstNE', 'xUZaDn2qlK6HyjbjsVFVH9') {'notifications': <queue.Queue object at 0x000001AF1A192190>, 'abort': <threading.Event at 0x1af1a1936d0: unset>, 'log': <calibre.utils.logging.GUILog object at 0x000001AF1A190CD0>}

[kovidgoyal]

read the FAQ https://manual.calibre-ebook.com/faq...-using-calibre in particular the note about gmail

[uncletoma]

Originally Posted by kovidgoyal

read the FAQ https://manual.calibre-ebook.com/faq...-using-calibre in particular the note about gmail

Ok, thanks a lot, but i'have the same error (username/password) using my @outlook.com account

[gbm]

Try this for gmail.

https://support.google.com/accounts/...60741837814-NA


bernie

Originally Posted by uncletoma

Ok, thanks a lot, but i'have the same error (username/password) using my @outlook.com account

[uncletoma]

Thanks a lot mate, i'll read it as soon as possible
It's for android apps, i'im using Calibre on PC with Windows 10

[DNSB]

You may also want to check into using app passwords since Google/GMail does not seem to permit most logins using the username/password.

See Sign in with app passwords for more information.

[uncletoma]

Ok, thanks a lot, but i got the same problem with outlook and yahoo accounts
later i'll try to reboot my pc and doing a calibre clean install