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Relaying Postfix SMTP via smtp.gmail.com

I’ve got a few servers in different places around the country and try to monitor them using the logwatch utility.  One problem that I’ve run into however is that a few of these servers are not able to send their logwatch emails to me, based on email restrictions by the ISPs.  I spent some time this afternoon researching what was required to have my servers authenticate to my gmail account and send me the mail that way.  This setup assumes Ubuntu 8.04 (or later) and Postfix.

Install the required packages

sudo aptitude install postfix libsasl2 ca-certificate libsasl2-modules

Configure Postfix

This tutorial will not outline how to configure your postfix server, but we’ll jump directly to the relayhost section.  You’ll want to add the following lines to your /etc/postfix/main.cf file:

relayhost = [smtp.gmail.com]:587
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options = noanonymous
smtp_tls_CAfile = /etc/postfix/cacert.pem
smtp_use_tls = yes

The above lines are telling Postfix that you want to relay mail through gmail on a specific port, telling it to authenticate, and where to find the username and password.  The last three lines specify the authentication types supported, where the certificate authority file is and that it should use tls.

Define Username and Password

Next we’ll need to populate the sasl_passwd file.  Create the file /etc/postfix/sasl_passwd with the following contents:

[smtp.gmail.com]:587    user.name@gmail.com:password

This file should have restrictive permissions and then needs to be translated into a .db that Postfix will read.

sudo chmod 400 /etc/postfix/sasl_passwd
sudo postmap /etc/postfix/sasl_passwd

At this point you can restart Postfix and it should work, however it will complain about not being able to authenticate the certificate.  To take care of this issue we’ll use the ca-certificate package we installed and tell it where it can validate the certificate.

cat /etc/ssl/certs/Thawte_Premium_Server_CA.pem | sudo tee -a /etc/postfix/cacert.pem

Go ahead and reload postfix (sudo /etc/init.d/postfix reload) and you should be set.

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  1. November 11th, 2008 at 11:35 | #1

    I think you should mention that this setup is only good for a postfix server that will be serving only a single user. Gmail will save every outgoing message this way in the Sent Mail “folder” belonging to the user authenticated against in the sasl_passwd file.

    This is usually not desired by a multiuser mail relay. However, it could be a good method to archive all outgoing email in a small organization.

  2. November 11th, 2008 at 11:54 | #2

    Thank you. I’ve been looking for a solution like this for some time now.

  3. jkl
    November 11th, 2008 at 12:40 | #3

    Thanks. This post was very useful!

  4. Hobbsee
    November 12th, 2008 at 01:00 | #4

    Things like msmtp and ssmtp are much lighter tools (either of them), and can be used to do the same things. Perhaps look into those?

    I’m using msmtp to go through the fastmail smtp servers (where I have an account), with no problems.

  5. jadesro
    November 26th, 2008 at 09:35 | #5

    I tried using these instructions yesterday on a newly installed ubuntu server 8.10 but got tripped up by the very first command: “sudo aptitude install postfix libsasl2 ca-certificate” reported that libasal2 was no longer available (it suggested libasal2-2) and that there was no such thing as ca-certificate. Just me?

  6. November 26th, 2008 at 13:59 | #6

    At least on debian testing I had to do:

    sudo apt-get install ca-certificates

    As for libsasl2, I use:

    $ apt-cache policy libsasl2
    libsasl2:
    Installed: 2.1.22.dfsg1-8
    Candidate: 2.1.22.dfsg1-8
    Version table:
    *** 2.1.22.dfsg1-8 0
    500 http://ftp.fr.debian.org stable/main Packages
    100 /var/lib/dpkg/status

  7. December 6th, 2008 at 23:00 | #7

    On Ubuntu 8.10 the package names have changed, as jadesro notes above. ca-certificates and libsasl2-2 are now the correct packages.

  8. January 29th, 2009 at 20:27 | #8

    i need smtp sever address for mailsoftwere
    plz help how to use &enable my smtp server
    mail me

  9. February 4th, 2009 at 05:43 | #9

    You are a genius. I’ve been struggling for 3 days to get sendmail or postfix to use SMTP but because I’m behind a residential dynamic IP address all emails get rejected with

    The IP you’re using to send mail is not authorized 550-5.7.1 to send email directly to our servers.

    Followed instructions exactly and it worked, except I already had sasl2 and ca.cerficiate installed. (Ubuntu 8.10 and postfix)

  10. go2null
    February 14th, 2009 at 17:40 | #10

    Please fix ca-certificate to ca-certificates

  11. Sureshkumar
    February 21st, 2009 at 06:08 | #11

    how can add 100 multiple users in the /etc/postfix/sasl_passwd…what is syntax
    already i was tried these syntax
    [smtp.gmail.com]:587 user1@gmail.com:user1
    [smtp.gmail.com]:587 user2@gmail.com:user2
    [smtp.gmail.com]:587 user3@gmail.com:user3

    [smtp.gmail.com]:587 usern@gmail.com:usern

    but it’s not working ………am waiting for your reply or if you please scrap my email id :krisuresh001@gmail.com

  12. February 22nd, 2009 at 07:54 | #12

    I am a new computer user at 70 yrs old.My outgoing failed, because my “smtp” failed.
    What to do thank, JACK W.

  13. March 1st, 2009 at 02:45 | #13

    Thanks! Thanks! Thanks! Thanks! Thanks! Thanks! :)

    In Mandriva 2009 have no ca-certificate.
    We must to install rootcerts:

    # urpmi rootcerts

    And add them:

    # cat /etc/pki/tls/cert.pem | tee -a /etc/postfix/cacert.pem

  14. March 21st, 2009 at 11:33 | #14

    I have followed your instructions, and I can’t seem to quite get things to work. I am running Ubuntu 8.10 and whenever I send an email to my email address, I get an “Undelivered Mail Returned to Sender” error email with the following error: “relay access denied (in reply to RCPT TO command)” or “Relay access denied (state 14).”

    In mail.log I see errors like this one:

    NOQUEUE: reject: RCPT from mail.domain.com[###.###.###.###]: 554 5.7.1 : Relay access denied; from= to= proto=ESMTP helo=

    Any thoughts on what I’m doing incorrectly?

  15. September 27th, 2009 at 15:50 | #15

    Nearly the whole article is a apt-link to libsasl.

  16. John Kerr
    February 7th, 2010 at 13:11 | #16

    Worked like a charm

    Thanks!!!

    John

  17. rupert
    February 11th, 2010 at 17:06 | #17

    Please use:
    $ sudo aptitude install postfix libsasl2-2 ca-certificates libsasl2-modules
    on Ubuntu.

  18. ubestos
    February 23rd, 2010 at 11:34 | #18

    thank you for this how to! It worked excellent with little changes on Ubuntu 9.10 but the Idea is right.

  19. June 21st, 2010 at 04:08 | #19

    Hi,

    I would like to have a scenario where local mails (or as specified in /etc/postfix/transport file) are delivered within server and rest are delivered through relayhost. If I use transport file, “relayhost = ” is left to empty.

    So, how can I use above information togther with transport feature in order to route certain emails locally as defined in transport file and rest using relayhost with ssl authorization (gmail account).
    thanks,

  20. July 13th, 2010 at 08:33 | #20

    i’ve tried many diffrent tutorials, this one worked like a charm!

    many thanks!

  21. August 1st, 2010 at 13:03 | #21

    This worked great on my Ubuntu 10.04 installation. Now I can finally sent SMART and mdadm mails from my home server.
    Thx for the great writeup!

  22. John
    August 20th, 2010 at 11:13 | #22

    Gmail now uses certificate from Equifax

    Use this instead of the Thawte certs

    cat /etc/ssl/certs/Equifax_Secure_CA.pem >> /etc/postfix/cacert.pem

  23. papukaija
    September 2nd, 2010 at 08:44 | #23

    Thanks John for the info about Gmail’s new certificate.