Configuring exim4 in Ubuntu to use GMail for SMTP

Hello,

wery useful, thanks. in my case (debian, exim4) I needed also to comment whole section starting from

login:

because I was geting

two client authenticators (gmail_login and login) have the same public name (LOGIN)

Excellent write up! This helped me a lot.

Thanks for this guide, worked like a charm after spending hours trying to get postfix to play nice with Gmail I found this solution to be 10x easier and I didn’t even have to mess with SSL CA certs ;)

http://basskozz.wordpress.com/2008/12/07/how-to-setup-a-raid5-software-mdadm-array-w-email-notifications-via-gmail-the-easy-way/

Thank you for the help. I’m running Ubuntu Gutsy and required an additional step not mentioned above.

From the site http://wiki.debian.org/GmailAndExim4 I found the following little snippet which for me was the final fix I needed:

==============
Run

# editor /etc/exim4/passwd.client

and add the following lines:

gmail-smtp.l.google.com:yourAccountName@gmail.com:y0uRpaSsw0RD
*.google.com:yourAccountName@gmail.com:y0uRpaSsw0RD
smtp.gmail.com:yourAccountName@gmail.com:y0uRpaSsw0RD
=============

After following this guide to the letter I was still getting “Authorization Required” errors in my exim4 mainlog file. Once I made the changes noted above delivery to gmail worked as expected.

Just to be sure, I just retested by disabling the changes to passwd.client. Followed the instruction as noted on this blog, then restarted exim4. Sending an email is once again returning the “Authorization Required” error from gmail.

Here is the exact error message:
2008-12-12 15:16:12 1LBEQb-00052L-11 ** root@parramoreworks.com R=smarthost T=remote_smtp_smarthost: SMTP error from remote mail server after MAIL FROM: SIZE=2462: host gmail-smtp-msa.l.google.com [74.125.47.111]: 530-5.5.1 Authentication Required. Learn more at\n530 5.5.1 http://mail.google.com/support/bin/answer.py?answer=14257 6sm2449761ywp.50

If you have any pointers on how to correct this without using the questionable wiki instructions I would be very appreciative.

Uh, thats a long file. Do you want me to post it here or send it to you in an email?

Thank you, thank you, thank you! That works perfectly. I really appreciate your help with this. I don’t how I missed that in the instructions. Twice even. arghh.

You’re the man! Great guide, worked perfectly.
Thank you so much.

Hello,
Good guide but still cant send emails.
I have no errors and my logs are empty.

Very handy, thanks a lot.

At the moment it doesn’t seem to be respecting /etc/aliases (specifically, trying to rewrite root), but that’s probably sticky fingers on my part. When/if I find a solution I’ll post a note here.

Regards

DAVE

Thanks for the great guide. I don’t know how many hours you just saved me, but its a lot. The instructions worked perfectly and they were easy to follow.

Thanks again,
Richard

My 2 cents….
Perhaps you can reword the guide above to say instead

If you have any other smarthost defined with “domains = ! +local_domains” remove that smarthost.

to
Comment out the entire smarthost: eg.

#smarthost:
# debug_print = “R: smarthost for $local_part@$domain”
# driver = manualroute
# domains = ! +local_domains
# transport = remote_smtp_smarthost
# route_list = * DCsmarthost byname
# host_find_failed = defer
# same_domain_copy_routing = yes
# no_more

Then add below
send_via_gmail:
driver = manualroute
domains = ! +local_domains
transport = gmail_smtp
route_list = * smtp.gmail.com

oh and one more thing –

if anyone gets stuck when you run
/ext/init.d/exim4 restart
and receive
ALERT:exim paniclog /var/log/exim4/paniclog has non-zero size, mail system possibly broken

I think this is a red hairing. delete/remove the old entries in the paniclog and this clears this error.

AWESOME – it’s working!

Many thanks for your article.

Instructions are very clear and straight.

IT WORKED, BRAVO !

Thanks, Nagin

Hmmm, I followed the instructions to a tea, twice, no errors, but mail never reaches it’s destination. Any thoughts?

BTW, I am running Exim4 on Debian Sarge…

Wonderful article. One question i have though! I have a firewall in my Hardy Heron server install, using UFW. Should i open port 587 to let the emails go out?

Thank you for your reply. This sure works for me!!! Thank you.

Thanks again, as I mentioned in an earlier comment I used this to setup exim4 on my NAS.

I am running into one problem however, my RIG is sending emails to root@domain.com. But I don’t own ‘domain.com’, how can I configure root emails (usually errors of some sort) to only send emails to my gmail address?

Thanks for the nice writeup.

One suggestion: changing the permissions of the exim4.conf.template file since it contains the gmail password in plain text (chmod 0600).

Does this solution send the gmail password as plaintext to the gmail smtp server? If so is it possible to use a secure connection?

Hi,

I agree, you should tell to comment out the whole smarthost definition.

I add to comment the end of the file in order to rid off an error on update-exim4.conf exec :

“client_send” option set for the second time

here is the end of my file :

#.ifndef AUTH_CLIENT_ALLOW_NOTLS_PASSWORDS
# client_send = “<; ${if !eq{$tls_cipher}{}\
# {^${extract{1}{:}{PASSWDLINE}}\
# ^${sg{PASSWDLINE}{\\N([^:]+:)(.*)\\N}{\\$2}}\
# }fail}”
#.else
# client_send = “<; ^${extract{1}{:}{PASSWDLINE}}\
# ^${sg{PASSWDLINE}{\\N([^:]+:)(.*)\\N}{\\$2}}”
#.endif

#login:
# driver = plaintext
# public_name = LOGIN

#.ifndef AUTH_CLIENT_ALLOW_NOTLS_PASSWORDS
# Return empty string if not non-TLS AND looking up $host in passwd-file
# yields a non-empty string; fail otherwise.
# client_send = “<; ${if and{\
# {!eq{$tls_cipher}{}}\
# {!eq{PASSWDLINE}{}}\
# }\
# {}fail}\
# ; ${extract{1}{::}{PASSWDLINE}}\
# ; ${sg{PASSWDLINE}{\\N([^:]+:)(.*)\\N}{\\$2}}”
#.else
# Return empty string if looking up $host in passwd-file yields a
# non-empty string; fail otherwise.
# client_send = “<; ${if !eq{PASSWDLINE}{}\
# {}fail}\
# ; ${extract{1}{::}{PASSWDLINE}}\
# ; ${sg{PASSWDLINE}{\\N([^:]+:)(.*)\\N}{\\$2}}”
#.endif
#####################################################
### end auth/30_exim4-config_examples
#####################################################

oups… spelling mistake :

“I add to comment the end of ”

should be read :

“I had to comment the end of …”

;o)

Note : if you did some config mistake before getting a correct file, on exim4 restart, you’ll get this warning :

* ALERT: exim paniclog /var/log/exim4/paniclog has non-zero size, mail system possibly broken

Which tells that the log file has something in it and you should look into.

Mine got these kind of message :

2009-02-08 00:35:50 Exim configuration error in line 834 of /var/lib/exim4/config.autogenerated.tmp:
“client_send” option set for the second time

Has it’s my previous mistake, you can safely delete the file to get rid off the warning and restart exim4.

Thomas

Great ! I got it working within 10 minutes ;o)

Question :

Mail are sent from :

root

Is it possible to customize some config file to have

root@machineName.domain.tld

Because I’ve several server to configure this way, And I want to know which one is mailing me.

Although, I’ve google Apps [premium] accout and for the login information you can use

yourGoogleAppsLogin@yourDomain.tld : yourpassword

and leave everything else as is, it will works too ;o)

Many thanks for the tutorial !
Thomas.

the comment system do not escape html :’(

Mail are sent from :

root <mygmailaddr@gmail.com>

Is it possible to customize some config file to have

root from machineName.domain.tld <mygmailaddr@gmail.com>

Awesome guide!
Can you configure it to only accept requests from 127.0.0.1 ?

Thanks, I haven’t really dared to touch iptables yet, apparently its time to check it out. ;)

You don’t need to touch iptables.

The tutorial configure Exim so that it accept smtp connection only on 127.0.0.1

* Type IP Adresses to listen on for incoming SMTP connections: 127.0.0.1

So it’s safe as Exim won’t bind on your public ip.

Though it’s a good practice to forbid ports that should be used from internet.

On ubuntu there’s ufw (uncomplicated firewall) which far less combersome to use than iptables.

Thanks a lot for this fine guide, saved me a lot of time. (using Ubuntu Gutsy and mdadm raid array notifications)

Works wonders, albeit I use your tutorial to guide me to setup on local smtp and actually skip #2 =)

and this is the first mailing system I handled.
Many many thanks to the guide.

Great!. Just wanted to thank you for this tutorial.

I keep getting these errors: http://pastebin.com/m13bc7895
exim4.conf.template: http://pastebin.com/m4ee71713

THIS IS DRIVING ME INSANE

Ok, i think it has something to do with my network though im out of ideas as to what it could be.

Telnet:
telnet: Unable to connect to remote host: Connection refused

Telnet using putty on my windows machine:
220 mx.google.com ESMTP v32sm740311wah.24

Ping:
From beasty-x12000 (192.168.1.3) icmp_seq=1 Destination Port Unreachable

Pinging from my windows machine works…

For some reason my debian server is being blocked, though they are plugged into the same switch and using the same gateway. This is just a home network so there isnt anything special set up, just a switch and a modem/router.

This is weird.

Great man.

Thanks for this tutorial worked like a charm.

The only thing I regret is that still configuring linux services in some distributions is so painful because you have to re-learn a new configuration layout though the concepts are the same (mta, relay, smtp, etc). Why not just having a simple GUI to do all this stuff.

Cheers,
Javier.

After some troubles, I have it working on Debian testing. Exim4 doesn’t work with my large and stupid isp (AT&T)[0] but since I’ll probably changes isp before gmail goes away, this works out better! Thanks!

[0] bugs.debian.org/430057

Took some time to look at this more and wanted to add some things:

- gmail supports tls and exim automatically uses it [0] so these connections should be secure. Someone asked earlier and I wanted to verify.

- email sent this way uses the linux login account’s name (not the email account’s name) in the From: field. I added a line like:
*@* “Your Name ” Ffrsw
in the rewrite/31_exim4-config_rewriting section to fix this.

Hope this is helpful and clear.

[0] http://pkg-exim4.alioth.debian.org/README/README.Debian.html#TLS

The *@* line didn’t show up right. After “Your Name is a .

You rock – works like a charm.

Thank you very much. Muchas Gracias.

It worked for me using Ubuntu 8.10 .

Thanks! Very good help!

As yotnottin mentioned before I applied tips from:
http://wiki.debian.org/GmailAndExim4

<quote>editor /etc/exim4/passwd.client

and add the following lines:

gmail-smtp.l.google.com:yourAccountName@gmail.com:y0uRpaSsw0RD
*.google.com:yourAccountName@gmail.com:y0uRpaSsw0RD
smtp.gmail.com:yourAccountName@gmail.com:y0uRpaSsw0RD

Run # chown root:Debian-exim /etc/exim4/passwd.client

The following only applies to exim 4.50 in sarge; in etch and sid the port can be configured via debconf with smtp.gmail.com::587. See the Debian exim docs for more detailed description.

* The following will only work in split configuration. Next, tell it what port to try. Run

# vi /etc/exim4/conf.d/transport/30_exim4-config_remote_smtp_smarthost and add the following line before the line containing “hosts_try_auth…”

port=587 Add your outgoing email-address to the /etc/exim4/email-addresses

# echo 'YOUR-USER-NAME@LocalHost: yourAccountName@gmail.com' >> /etc/exim4/email-addresses

Finally for all versions of Debian, run

# update-exim4.conf
</quote>

After this it works fine. Kind regards for your work

This site is rally good :)

http://24×7jobs-solution.blogspot.com/

Thanks Manu for the excellent write up!…..and thanks to John Pope for mentioning about the paniclog issue. Now I got a debian lenny set up from where I can send mail to the outside world.

I needed this as I am working away from home with a static IP address. Now I am getting mail everyday with my new IP, ISP changes it after every 24 hours.
But I got a problem now. Every cronjob sends its output to my external mail, not to the email I put in the exim configuration file but to the email ID where I am getting the IP update. Howz this possible and how can In resolve this????

Hi Manu,
thanks for the documet. helped me totally. great work.
thanks again.

This is great! I got it working — Thanks! I have one small issue. In wordpress, I have a contact 7 form. When I send the email, I want the return-address to show that of the person who sent the email… not the gmail account I programmed into exim4… you know what I mean?

So in wordpress, in the from section, I place a variable: [your-name] … which corresponds to the email address that the sender typed in. But When I open the email, it looks like it is from exim4’s gmail account.

Please help!

@manu: Thanks. I made a ‘contactus’ address, so it makes sense. I had one more question in the same area:

exim4 seems to add the logged-in linux user’s name as the sender’s name. Is there a way I can tell exim4 which name to put? ie: if I am logged in as Alfred Inacio, and my username is ainaico… even though the emails are sent from contactus@peoplewithbandaids.com, it still shows my name (Alfred Inacio) as the sender.

Thanks!

I noticed one more problem.
If your password has a $ sign, you wont be able to send it.
To rectify this problem, add a \ before the $ sign.
Example :- pass$word will become pass\$word

@ Bilal

There are a few characters in php which require escaping:
\n linefeed (LF or 0×0A (10) in ASCII)
\r carriage return (CR or 0×0D (13) in ASCII)
\t horizontal tab (HT or 0×09 (9) in ASCII)
\v vertical tab (VT or 0×0B (11) in ASCII) (since PHP 5.2.5)
\f form feed (FF or 0×0C (12) in ASCII) (since PHP 5.2.5)
\\ backslash
\$ dollar sign
\” double-quote