Update:
Javin,
I hope I assembled the openssl test into an ssh script
the result ended with (about)
return code 0 O.K.

so, it appears I do have proper ssl connection with fastmail, now I
guess
back to why my .muttrc doesn't send.
Guess I'll try setting up msmtp with example provided here.
thanks all
  Tom Fowle
  wa6iv...@fastmail.fm


On Thu, Nov 20, 2014, at 10:55 AM, JaviM wrote:
> > 
> > libsasl2 is installed.
> > snip from .muttrc
> > 
> > set my_server=mail.messagingengine.com
> > set my_smtp_server=mail.messagingengine.com
> > set my_user=wa6iv...@fastmail.fm
> > set my_pass = "********"
> > 
> > set header_cache=~/.mutt/hcache/fastmail
> > 
> > set imap_user=$my_user
> > set imap_pass = $my_pass
> > #
> > set smtp_url ="smtps://$my_user:$my_pass@$my_smtp_server:465"
> > 
> 
> Hi:
> 
> 1) please, run this command on terminal and post the output:
> 
>    ldd $(which mutt)
> 
> 
> 2) you should discard errors in the network from mutt 
> to fastmail SMTP servers
>       mail.messagingengine.com:465   SSL
>       mail.messagingengine.com:587   STARTTLS
> 
> If
>       username= wa6iv...@fastmail.fm
>       password= mysecret
>       ssl certificates are kept in /etc/ssl/certs
> then, follow following steps.
> 
> First, calculate hashed base64 representation of your real
> username+password with:
> 
>       printf "\0wa6iv...@fastmail.fm\0mysecret" | openssl enc -a
> 
> or equivalent command with perl:
>       perl -MMIME::Base64 -e 'print 
> encode_base64("\000wa6iv...@fastmail.fm\000mysecret")'
> 
> 
> Hashed string will be similar to:
>       AHlvdXJfdXNlcm5hbWUAeW91cl9wYXNzd29yZA==
> 
> 
> Then, try an openssl connection:
>       $ openssl s_client -connect mail.messagingengine.com:465 -crlf -ign_eof 
> -CApath /etc/ssl/certs 
>       [...]
>       EHLO localhost
>       [...]
>       AUTH PLAIN AHlvdXJfdXNlcm5hbWUAeW91cl9wYXNzd29yZA==
> In this point, you will receive a "OK"/"Accepted" or similar
> successfull message. If not, you have problems in fastmail servers,
> and you will need to check configuration in fastmail control panel.
> 
> Check also STARTTLS port:
>       $ openssl s_client -starttls smtp -connect mail.messagingengine.com:587 
> -crlf -ign_eof -CApath /etc/ssl/certs 
> 
> 
> If you send logs from above commands, PLEASE, dont include your real
> hashed string (similar to AHlvdXJfdXNlcm5hbWUAeW91cl9wYXNzd29yZA==):
> it is equivalent to your real username and password. 
> 
> 
> 
> References:
> http://stackoverflow.com/questions/11046135/how-to-send-email-using-simple-smtp-commands-via-gmail
> http://ghost.deuterion.net/smtp-debugging-smtp-with-tlsssl-and-auth/
> 
> 
> 

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