Can’t connect to SMTP over 587

emailemail-serversaslsmtp

I am setting up a mail server, on Ubuntu, based on: https://help.ubuntu.com/community/Postfix

Currently, I can both send and receive email from the server. However, attempts to send email through SMTP from gmail fail with a bad authentication. I've verified my password, ensured that the port is open, and am able to telnet to the IP and port.

Telnet output (from remote host)

Computer:~ Louis$ telnet mail.mysite.com 587
Trying 71.66.218.124...
Connected to mail.mysite.com (71.66.218.124).
Escape character is '^]'.
220 mail.mysite.com ESMTP Postfix
ehlo mail.mysite.com
250-mail.mysite.com
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH DIGEST-MD5 NTLM CRAM-MD5 PLAIN LOGIN
250-AUTH=DIGEST-MD5 NTLM CRAM-MD5 PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN

And, testing my login information:

sudo testsaslauthd -u jon -p ********
0: OK "Success."

And currently listening ports:

netstat -ln
Active Internet connections (only servers)
Proto Recv-Q Send-Q Local Address           Foreign Address         State      
tcp        0      0 0.0.0.0:587             0.0.0.0:*               LISTEN     
tcp        0      0 0.0.0.0:80              0.0.0.0:*               LISTEN     
tcp        0      0 0.0.0.0:22              0.0.0.0:*               LISTEN     
tcp        0      0 0.0.0.0:25              0.0.0.0:*               LISTEN     
tcp6       0      0 :::587                  :::*                    LISTEN     
tcp6       0      0 :::110                  :::*                    LISTEN     
tcp6       0      0 :::143                  :::*                    LISTEN     
tcp6       0      0 :::4949                 :::*                    LISTEN     
tcp6       0      0 :::22                   :::*                    LISTEN     
tcp6       0      0 :::25                   :::*                    LISTEN

Any idea why I cannot remotely configure my SMTP to send email?

EDIT

I am preferential to gmail's interface, and would like to aggregate all of my mail on one online service. I can add my POP3 account on gmail (settings > accounts > Add a POP3 Mail Account Of Your Own). After successfully authenticating with my server, I am asked if I'd like to send email through my servers smtp, to which I say yes. When I try and login, I get the following message:

Authentication failed. Please check your username/password. [Server
response: 535 5.7.8 Error: authentication failed: authentication
failure code(535) ]

I should note, this is not a gmail problem – I cannot authenticate from ANY device or application over smtp. However, I can authenticate using the tools on the server, and over telnet . . .

EDIT 2

Errors from /var/log/mail.log

Feb 2 14:52:42 Mysite postfix/smtpd[16527]: connect from
mail-ea0-f76.google.com[102.85.215.76] Feb 2 14:52:43 Mysite
postfix/smtpd[16527]: Anonymous TLS connection established from
mail-ea0-f76.google.com[102.85.215.76]: TLSv1 with cipher
ECDHE-RSA-RC4-SHA (128/128 bits) Feb 2 14:52:43 Mysite
postfix/smtpd[16527]: warning: SASL authentication failure: Password
verification failed Feb 2 14:52:43 Mysite postfix/smtpd[16527]:
warning: mail-ea0-f76.google.com[102.85.215.76]: SASL PLAIN
authentication failed: authentication failure Feb 2 14:52:43 Mysite
postfix/smtpd[16527]: disconnect from
mail-ea0-f76.google.com[102.85.215.76]

EDIT 3
Here's my /etc/postfix/main.cf as requested.

mydomain = mysite.com
biff = no
append_dot_mydomain = no
smtpd_tls_cert_file = /etc/ssl/certs/smtpd.crt
smtpd_tls_key_file = /etc/ssl/private/smtpd.key
smtpd_use_tls=yes
smtpd_tls_session_cache_database = btree:${queue_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${queue_directory}/smtp_scache
smtp_sasl_auth_enable = yes
# password maps will not work. Customer must provide credentials
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options = noanonymous
smtp_use_tls = yes
myorigin = /etc/mailname
smtpd_banner = $myhostname ESMTP $mail_name 
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
mydestination = mysite.localdomain, mysite, localhost.localdomain, localhost, mail.mysite.com, mysite.com
relayhost = 
mynetworks = 127.0.0.0/8
inet_interfaces = all
mailbox_size_limit = 0
recipient_delimiter = +
myorigin = mysite.com
inet_protocols = all
smtpd_sasl_local_domain = 
smtpd_sasl_auth_enable = yes
smtpd_sasl_security_options = noanonymous
broken_sasl_auth_clients = yes
smtpd_recipient_restrictions = permit_sasl_authenticated,permit_mynetworks,reject_unauth_destination
smtp_tls_security_level = may
smtpd_tls_security_level = may
smtpd_tls_auth_only = no
smtp_tls_note_starttls_offer = yes
smtpd_tls_CAfile = /etc/ssl/certs/cacert.pem
smtpd_tls_loglevel = 1
smtpd_tls_received_header = yes
smtpd_tls_session_cache_timeout = 3600s
tls_random_source = dev:/dev/urandom
myhostname = mail.mysite.com 
home_mailbox = Maildir/
mailbox_command = 
virtual_alias_domains = mysite.com
virtual_alias_maps = hash:/etc/postfix/virtual

Best Answer

SASL Authentication Check List

Base on question and comments, sasl may not be setup correctly. Following check list is created base on Ubunut Guide provided in question.

  1. Check file/etc/postfix/sasl/smtpd.conf, should be like following

    pwcheck_method: saslauthd
mech_list: plain login

  2. Check libsasl installed

    dpkg -l | grep sasl

    Should have the following (version number may differ)

    ii  libsasl2-2           2.1.25.dfsg1-4    Cyrus SASL - authentication abstraction library
ii  libsasl2-modules     2.1.25.dfsg1-4    Cyrus SASL - pluggable authentication modules
ii  sasl2-bin            2.1.25.dfsg1-4    Cyrus SASL - administration programs for SASL users database

  3. Check saslauthd is running

    ps -ef | grep sasl

  4. Check saslauthd PWDIR

    grep PWDIR /etc/default/saslauthd

    Output should be

    PWDIR="/var/spool/postfix/var/run/saslauthd"

Postfix submission/587

  1. /etc/postfix/master.cf

    The Ubuntu guide only un-comment one line

    submission inet n       -       -       -       -       smtpd

    Try ucomment the whole section, including the options following it

    submission inet n       -       -       -       -       smtpd
  -o smtpd_tls_security_level=encrypt
  -o smtpd_sasl_auth_enable=yes
  -o smtpd_client_restrictions=permit_sasl_authenticated,reject
  -o milter_macro_daemon_name=ORIGINATING

    Then restart postfix

    sudo service postfix restart

  2. Double check your smtp login name

    Since the guide is not using virtual user, your smtp login name should be joe only, not joe@mysite.com. Double check email clients on your deivces/computers/webservices(gmail) are NOT using your email address as smtp login name. (Many do that for you. You will have to manually change it if so.)

  3. Remove Password Map

    I believe you are authenticating against local Linux account, not virtual user. Remove the following lines in /etc/postfix/main.cf

    # password maps will not work. Customer must provide credentials
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
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