> 
> 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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