Ok I chanced the setting and also used the @kindle.com address
This is what I have this time
Email Instapaper.com to
xxxx@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '421 Cannot establish SSL with SMTP server 209.85.227.109:587, SSL_connect error 5\r\n'
reply: retcode (421); Msg: Cannot establish SSL with SMTP server 209.85.227.109:587, SSL_connect error 5
connect: Cannot establish SSL with SMTP server 209.85.227.109:587, SSL_connect error 5
send: 'ehlo [192.168.0.2]\r\n'
Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 105, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 628, in starttls
File "site-packages\calibre\utils\smtplib.py", line 528, in ehlo_or_helo_if_needed
File "site-packages\calibre\utils\smtplib.py", line 401, in ehlo
File "site-packages\calibre\utils\smtplib.py", line 358, in getreply
SMTPServerDisconnected: Connection unexpectedly closed
Retrying in 301 seconds...
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '421 Cannot establish SSL with SMTP server 209.85.227.109:587, SSL_connect error 5\r\n'
reply: retcode (421); Msg: Cannot establish SSL with SMTP server 209.85.227.109:587, SSL_connect error 5
connect: Cannot establish SSL with SMTP server 209.85.227.109:587, SSL_connect error 5
send: 'ehlo [192.168.0.2]\r\n'
Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 105, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 628, in starttls
File "site-packages\calibre\utils\smtplib.py", line 528, in ehlo_or_helo_if_needed
File "site-packages\calibre\utils\smtplib.py", line 401, in ehlo
File "site-packages\calibre\utils\smtplib.py", line 358, in getreply
SMTPServerDisconnected: Connection unexpectedly closed