Hello - I'm having a similar problem.
I've entered my gmail information to calibre, using my full username and the smtp server.
I have my email address enabled as an accepted sending address in amazon's list.
I get the following error message. Any help would be appreciated!
Traceback (most recent call last):
File "site-packages/calibre/gui2/wizard/send_email.py", line 115, in test_email_settings
File "site-packages/calibre/utils/smtp.py", line 103, in sendmail
File "site-packages/calibre/utils/smtplib.py", line 303, in connect
File "site-packages/calibre/utils/smtplib.py", line 777, in _get_socket
File "lib/python2.7/socket.py", line 571, in create_connection
error: [Errno 61] Connection refused