Calibre will not send via Gmail any more

[grifforama]

I keep getting this error.
I have recently upgraded my kindle to a paperwhite, but haven't changed anything in Calibre.



Traceback (most recent call last):
File "site-packages\calibre\gui2\wizard\send_email.py", line 203, in test_email_settings
File "site-packages\calibre\utils\smtp.py", line 135, in sendmail
File "site-packages\calibre\utils\smtp.py", line 127, in sendmail_direct
IOError: Failed to send mail: error(10060, 'A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond')


Log:
Find mail exchanger for kindle.com
connect: ('retail-smtp-in.amazon.com.', 25)
connect: ('retail-smtp-in.amazon.com.', 25)
Traceback (most recent call last):
File "site-packages\calibre\utils\smtp.py", line 120, in sendmail_direct
File "site-packages\calibre\utils\smtplib.py", line 334, in connect
File "site-packages\calibre\utils\smtplib.py", line 309, in _get_socket
File "socket.py", line 571, in create_connection
error: [Errno 10060] A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond

[theducks]

I don't think this has anything to do with your new kindle.

The message says Gmail never completed the handshake.
This might be caused by your firewall software being updated. Have you allowed' Calibre.exe to make network connections?

[kovidgoyal]

You are not sending via gmail according to that log. https://manual.calibre-ebook.com/faq...-using-calibre