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totte_karlsson 26th August 2009 03:02

Sending email with postfix, relay host, STARTTLS problem?
Hi, I have setup a (ISP config) server following the steps in

I want to send email using my isp providers smtp server (

I have edited /etc/postfix/ and added/changed
relayhost =
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd

When trying to send email I get this in mail.log

Aug 25 16:56:15 isp1 postfix/smtp[10711]: B3423E220A: to=<>,[]:25, delay=0.67, delays=0.03/0.09/0.44/0.12, dsn=5.7.0, status=bounced (host[] said: 530 5.7.0 Must issue a STARTTLS command first (in reply to MAIL FROM command))
Aug 25 16:56:15 isp1 postfix/cleanup[10690]: 8ACA7E2220: message-id=<>

Anyone knowing the steps to get this working with the ISPConfig 3 setup?


falko 26th August 2009 19:14

Can you run

telnet localhost 25
and then type

ehlo localhost
What's the output?

totte_karlsson 26th August 2009 20:17

Here is the output;

tk@isp1:~$ telnet localhost 25
Trying ::1...
Connected to localhost.
Escape character is '^]'.
220 ESMTP Postfix (Ubuntu)
ehlo localhost
250 DSN

I guess the PLAIN LOGIN is a problem?
Here is my

smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h

readme_directory = /usr/share/doc/postfix

# TLS parameters
smtpd_tls_cert_file = /etc/postfix/smtpd.cert
smtpd_tls_key_file = /etc/postfix/smtpd.key
smtpd_use_tls = yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

# See /usr/share/doc/postfix/TLS_README.gz in the postfix-doc package for
# information on enabling SSL in the smtp client.

myhostname =
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination =, localhost, localhost.localdomain
relayhost = []
mynetworks = [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
html_directory = /usr/share/doc/postfix/html
virtual_alias_domains =
virtual_alias_maps = proxy:mysql:/etc/postfix/, mysql:/etc/postfix/
virtual_mailbox_domains = proxy:mysql:/etc/postfix/
virtual_mailbox_maps = proxy:mysql:/etc/postfix/
virtual_mailbox_base = /var/vmail
virtual_uid_maps = static:5000
virtual_gid_maps = static:5000
smtpd_sasl_auth_enable = yes
broken_sasl_auth_clients = yes
smtpd_sasl_authenticated_header = yes
smtpd_recipient_restrictions = permit_mynetworks, permit_sasl_authenticated, check_recipient_access mysql:/etc/postfix/, reject_unauth_destination
smtpd_tls_security_level = may
transport_maps = proxy:mysql:/etc/postfix/
relay_domains = mysql:/etc/postfix/
virtual_create_maildirsize = yes
virtual_maildir_extended = yes
virtual_mailbox_limit_maps = proxy:mysql:/etc/postfix/
virtual_mailbox_limit_override = yes
virtual_maildir_limit_message = "The user you are trying to reach is over quota."
virtual_overquota_bounce = yes
proxy_read_maps = $local_recipient_maps $mydestination $virtual_alias_maps $virtual_alias_domains $virtual_mailbox_maps $virtual_mailbox_domains $relay_recipient_maps $relay_domains $canonical_maps $sender_canonical_maps $recipient_canon
smtpd_sender_restrictions = check_sender_access mysql:/etc/postfix/
smtpd_client_restrictions = check_client_access mysql:/etc/postfix/
maildrop_destination_concurrency_limit = 1
maildrop_destination_recipient_limit = 1
virtual_transport = maildrop
header_checks = regexp:/etc/postfix/header_checks
mime_header_checks = regexp:/etc/postfix/mime_header_checks
nested_header_checks = regexp:/etc/postfix/nested_header_checks
body_checks = regexp:/etc/postfix/body_checks
content_filter = amavis:[]:10024
receive_override_options = no_address_mappings
message_size_limit = 0
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options =
smtpd_tls_auth_only = no

falko 27th August 2009 13:56

Looks ok to me... :confused:

totte_karlsson 27th August 2009 19:06

I got it working!

Here is what I changed. In the, shown above,
changed/added the following lines

#changed from no to yes (may not matter for sending mail?)
smtpd_tls_auth_only = yes

#Added this line
smtp_tls_security_level = may

I also found a problem in my sasl passwd file:

[] 'useraccountname:my password'

However, I still have the following problems. If I send an email from a ssh shell, the email from address is
I can't figure out where comes from. If I send email using squirrel mail from an account created with ispconfig(3), the email "from" domain is correct.

Also, in the mail.log file, I get this "warning" for each mail that is relayed:
Aug 27 10:30:58 isp1 postfix/smtp[26534]: certificate verification failed for[]:25: untrusted issuer /C=US/O=GTE Corporation/OU=GTE CyberTrust Solutions, Inc./CN=GTE CyberTrust Global Root
Not sure how to get rid of that, not sure if I want since mail sending does work now.

Anyone knows where to set to my correct domain?


falko 28th August 2009 14:24

You must always set the correct sender address in your email client (Outlook, Thunderbird, webmail, on the command line, etc.). What command did you use to send the email? Did you take a look at its man page to find out how to set the sender address?

totte_karlsson 28th August 2009 18:26

Thanks Falko,
There is no problem with Thunderbird or Outlook, they both send email fine. It is from a command prompt, on the actual hosting machine, using the mail command, i.e.

tk@isp1:~$ echo "Hello" | mail -s"a subject" ToSomeEmailAddress

The hostname is and my username is tk. In the received mail on the other end, the from address is, not

Any help is appreciated,

falko 29th August 2009 14:14

I guess you can set the sender with the -a switch. See

man mail

totte_karlsson 29th August 2009 19:32

Thanks for suggestion, but I do suspect the the mail "from address" domain is taken from /etc/mailname which contains at the moment.

Can I just edit it with vi, or do I need to reconfigure something. Can I change it from within ISPConfig 3?


falko 30th August 2009 13:14

If the sender address is the only issue you're having, I'd not change the name of the mailserver - you might get yourself into trouble.


Can I change it from within ISPConfig 3?

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