[markhenry788]

For a couple of days, I had no problem sending news to my kindle.
In fact, I had been sending Business Insider and The Economist together for a while. However, although I'm having no problem with the latter, whenever I try to send Business Insider which is much smaller than The Economist and certainly much smaller than any book I can easily send, I get an error message. I tried to remove Business Insider from the auto-send list and added again nothing changed. Any help would so be appreciated.

Spoiler:

calibre, version 5.21.0 (win32, embedded-python: True)
Failed to email book: Failed: Email Business Insider to selimtemizyurek@kindle.com

Starting job: Email Business Insider to selimtemizyurek@kindle.com
connect: ('imap.gmail.com', 587)
connect: to ('imap.gmail.com', 587) None
reply: b'220 smtp.gmail.com ESMTP n13sm8115413ejk.97 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP n13sm8115413ejk.97 - gsmtp'
connect: b'smtp.gmail.com ESMTP n13sm8115413ejk.97 - gsmtp'
send: 'ehlo [192.168.1.45]\r\n'
reply: b'250-smtp.gmail.com at your service, [88.241.251.208]\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, [88.241.251.208]\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 [192.168.1.45]\r\n'
reply: b'250-smtp.gmail.com at your service, [88.241.251.208]\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, [88.241.251.208]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nCHUNKING\ nSMTPUTF8'
send: AUTH <censored>
reply: b'235 2.7.0 Accepted\r\n'
reply: retcode (235); Msg: b'2.7.0 Accepted'
send: 'mail FROM:<mykeynoteselim@gmail.com> size=85050605\r\n'
reply: b"552-5.2.3 Your message exceeded Google's message size limits. Please visit\r\n"
reply: b'552-5.2.3 https://support.google.com/mail/?p=MaxSizeError to view our size\r\n'
reply: b'552 5.2.3 guidelines. n13sm8115413ejk.97 - gsmtp\r\n'
reply: retcode (552); Msg: b"5.2.3 Your message exceeded Google's message size limits. Please visit\n5.2.3 https://support.google.com/mail/?p=MaxSizeError to view our size\n5.2.3 guidelines. n13sm8115413ejk.97 - gsmtp"
send: 'rset\r\n'
reply: b'250 2.1.5 Flushed n13sm8115413ejk.97 - gsmtp\r\n'
reply: retcode (250); Msg: b'2.1.5 Flushed n13sm8115413ejk.97 - gsmtp'
send: 'quit\r\n'
reply: b'221 2.0.0 closing connection n13sm8115413ejk.97 - gsmtp\r\n'
reply: retcode (221); Msg: b'2.0.0 closing connection n13sm8115413ejk.97 - gsmtp'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 195, in sendmail
File "smtplib.py", line 970, in send_message
File "smtplib.py", line 871, in sendmail
smtplib.SMTPSenderRefused: (552, b"5.2.3 Your message exceeded Google's message size limits. Please visit\n5.2.3 https://support.google.com/mail/?p=MaxSizeError to view our size\n5.2.3 guidelines. n13sm8115413ejk.97 - gsmtp", 'mykeynoteselim@gmail.com')


Retrying in 301 seconds...

Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: ('imap.gmail.com', 587)
connect: to ('imap.gmail.com', 587) None
reply: b'220 smtp.gmail.com ESMTP g11sm9845892edt.85 - gsmtp\r\n'
reply: retcode (220); Msg: b'smtp.gmail.com ESMTP g11sm9845892edt.85 - gsmtp'
connect: b'smtp.gmail.com ESMTP g11sm9845892edt.85 - gsmtp'
send: 'ehlo [192.168.1.45]\r\n'
reply: b'250-smtp.gmail.com at your service, [88.241.251.208]\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, [88.241.251.208]\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 [192.168.1.45]\r\n'
reply: b'250-smtp.gmail.com at your service, [88.241.251.208]\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, [88.241.251.208]\nSIZE 35882577\n8BITMIME\nAUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH\nENHANCEDSTATUSCODES\nPIPELINING\nCHUNKING\ nSMTPUTF8'
send: AUTH <censored>
reply: b'235 2.7.0 Accepted\r\n'
reply: retcode (235); Msg: b'2.7.0 Accepted'
send: 'mail FROM:<mykeynoteselim@gmail.com> size=85050605\r\n'
reply: b"552-5.2.3 Your message exceeded Google's message size limits. Please visit\r\n"
reply: b'552-5.2.3 https://support.google.com/mail/?p=MaxSizeError to view our size\r\n'
reply: b'552 5.2.3 guidelines. g11sm9845892edt.85 - gsmtp\r\n'
reply: retcode (552); Msg: b"5.2.3 Your message exceeded Google's message size limits. Please visit\n5.2.3 https://support.google.com/mail/?p=MaxSizeError to view our size\n5.2.3 guidelines. g11sm9845892edt.85 - gsmtp"
send: 'rset\r\n'
reply: b'250 2.1.5 Flushed g11sm9845892edt.85 - gsmtp\r\n'
reply: retcode (250); Msg: b'2.1.5 Flushed g11sm9845892edt.85 - gsmtp'
send: 'quit\r\n'
reply: b'221 2.0.0 closing connection g11sm9845892edt.85 - gsmtp\r\n'
reply: retcode (221); Msg: b'2.0.0 closing connection g11sm9845892edt.85 - gsmtp'

Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 195, in sendmail
File "smtplib.py", line 970, in send_message
File "smtplib.py", line 871, in sendmail
smtplib.SMTPSenderRefused: (552, b"5.2.3 Your message exceeded Google's message size limits. Please visit\n5.2.3 https://support.google.com/mail/?p=MaxSizeError to view our size\n5.2.3 guidelines. g11sm9845892edt.85 - gsmtp", 'mykeynoteselim@gmail.com')

Job: "Email Business Insider to selimtemizyurek@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 102, in __call__
File "calibre\gui2\email.py", line 45, in run
File "calibre\gui2\email.py", line 129, in sendmail
File "calibre\utils\smtp.py", line 195, in sendmail
File "smtplib.py", line 970, in send_message
File "smtplib.py", line 871, in sendmail
smtplib.SMTPSenderRefused: (552, b"5.2.3 Your message exceeded Google's message size limits. Please visit\n5.2.3 https://support.google.com/mail/?p=MaxSizeError to view our size\n5.2.3 guidelines. g11sm9845892edt.85 - gsmtp", 'mykeynoteselim@gmail.com')

Called with args: ('C:\\Users\\Lenovo\\AppData\\Local\\Temp\\calibre _fdtye7a1\\fdx9vvz5caltmpfmt.mobi', 'Business Insider - calibre.mobi', 'selimtemizyurek@kindle.com', 'E-book: Business Insider', 'Attached, you will find the e-book\n\nBusiness Insider\n\tby calibre\n\nin the MOBI format.') {'notifications': <queue.Queue object at 0x0E04D730>, 'abort': <threading.Event object at 0x0E04D7A8>, 'log': <calibre.utils.logging.GUILog object at 0x0E04D8C8>}