Comments on: Configure sendmail to work with Gmail smtp relay

By: Allan Brinton

Allan Brinton — Sun, 29 Jan 2012 09:00:26 +0000

Thanks-a-mundo for the post.Really thank you! Wonderful.

By: Marco

Marco — Thu, 05 Jan 2012 22:04:12 +0000

Thank you, thank you, thank you for your tutorial. I have discovered another caveat though.

If you are using a *brand new* Gmail account you may get the following error in /var/log/maillog:

relay=smtp.gmail.com, dsn=5.0.0, stat=Service unavailable

One cause for this error is that you have to log-in at least once into your Gmail account from your browser! This is due to the fact that Google needs you to accept the terms of service.

After spending half a day tweaking my sendmail configuration I finally bothered to read a “Delivery Status Notification” that bounced back and it was right there in front of my eyes:

—– Transcript of session follows —–
… while talking to smtp.gmail.com:
>>> AUTH dialogue
<<< 535-5.7.1 Please log in with your web browser and then try again. Learn more
at
<<< 535 5.7.1 https://mail.google.com/support/bin/answer.py?answer=78754 cv10sm1
20709067igc.0

It never hurts to double check every part of your system!

By: Setup sendmail (notifications) for GMAIL SMTP « darryn van tonder

Setup sendmail (notifications) for GMAIL SMTP « darryn van tonder — Wed, 04 Jan 2012 04:44:56 +0000

[...] for a long time now and needed to configure my server to relay mail through it. Here’s a nice article that walks you through exactly what needs to be done to configure your sendmail MTA to relay [...]

By: Gmail SMTP? sendmail ???? ???? « Help Work

Gmail SMTP? sendmail ???? ???? « Help Work — Mon, 10 Oct 2011 08:50:35 +0000

[...] http://www.phinesolutions.com/sendmail-gmail-smtp-relay-howto.html Like this:LikeBe the first to like this [...]

By: mav3

mav3 — Wed, 31 Aug 2011 10:28:45 +0000

hi folks,

iam getting this error, any idea?

m4:sendmail.mc:176: Warning: excess arguments to builtin `define’ ignored
m4:sendmail.mc:176: cannot open `/usr/share/sendmail-cf/feature/’authinfo’.m4′: No such file or directory
*** ERROR: MAILER(smtp) already included

My config

FEATURE(‘authinfo’,’hash /etc/mail/client-info.db’)dnl
define(‘SMART_HOST’,’smtp.gmail.com’)dnl
define(‘RELAY_MAILER_ARGS’, ‘TCP $h 587?)
define(‘ESMTP_MAILER_ARGS’, ‘TCP $h 587?)
define(‘CERT_DIR’, ‘/etc/mail/certs’)
define(‘confCACERT_PATH’, ‘CERT_DIR’)
define(‘confCACERT’, ‘CERT_DIR/ca-bundle.crt’)
define(‘confCRL’, ‘CERT_DIR/ca-bundle.crt’)
define(‘confSERVER_CERT’, ‘CERT_DIR/sendmail.pem’)
define(‘confSERVER_KEY’, ‘CERT_DIR/sendmail.pem’)
define(‘confCLIENT_CERT’, ‘CERT_DIR/sendmail.pem’)
define(‘confCLIENT_KEY’, ‘CERT_DIR/sendmail.pem’)
define(‘confAUTH_MECHANISMS’, ‘EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN’)
TRUST_AUTH_MECH(‘EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN’)

By: vne

vne — Mon, 29 Aug 2011 07:42:50 +0000

Hi,
Thanks a lot for the help…my issue got resolved by following the trail comments…

Thanks a lot again..

By: Easiest way to configure local SMTP server to relay through gmail on Windows? - Admins Goodies

Sun, 21 Aug 2011 08:33:16 +0000

[...] I need to use something like sendmail to do this – or some other free SMTP relay that gives me better control? I even found a sourceforge [...]

By: WrinkledCheese

WrinkledCheese — Fri, 29 Jul 2011 20:01:13 +0000

I followed this and I was getting service unavailable. So I started reading comments. I added the line MAILER(smtp)dnl and everything seemed to work.

Here is my sendmail.mc
include(`../m4/cf.m4′)
VERSIONID(`GMail Support’)dnl
OSTYPE(`linux’)dnl
FEATURE(`authinfo’,`hash /etc/mail/client-info.db’)dnl
define(`SMART_HOST’,`smtp.gmail.com’)dnl
define(`RELAY_MAILER_ARGS’, `TCP $h 587′)
define(`ESMTP_MAILER_ARGS’, `TCP $h 587′)
define(`CERT_DIR’, `/etc/mail/certs’)
define(`confCACERT_PATH’, `CERT_DIR’)
define(`confCACERT’, `CERT_DIR/ca-bundle.crt’)
define(`confCRL’, `CERT_DIR/ca-bundle.crt’)
define(`confSERVER_CERT’, `CERT_DIR/sendmail.pem’)
define(`confSERVER_KEY’, `CERT_DIR/sendmail.pem’)
define(`confCLIENT_CERT’, `CERT_DIR/sendmail.pem’)
define(`confCLIENT_KEY’, `CERT_DIR/sendmail.pem’)
define(`confAUTH_MECHANISMS’, `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN’)
TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN’)
define(`confAUTH_OPTIONS’, `A’)dnl
MAILER(smtp)dnl

I am running Slackware so I copy this to /usr/share/sendmail/cf/cf so that the include line works. Due to the size of cf.m4 and it’s includes, I will leave them out. If you want to see them get a copy of slackware, or browse an online repository, and look for /usr/share/sendmail/cf/m4 which should be in the sendmail package for slackware.

I will also note that I successfully sent an email without the ca-bundle.cert

By: Johnny

Johnny — Sat, 23 Jul 2011 18:26:03 +0000

This is really a great write-up! It could do with placing a note adjacent to the code-sections though, in the lines of:

NOTE: Be aware that smart-quotes used in the code examples will not be recognised if pasted into your files! Ensure replacing smart-quotes by regular quotes (see comments below for further detail).

or similar. I spent a frustrating three hours due to this before finally scrolling down to read some of the comments. But as soon as I realised that, a flawless writeup!

By: Joe

Joe — Tue, 12 Jul 2011 03:52:00 +0000

Why install your own sendmail just to route it back to gmail. The whole object of this exercise should be to avoid your mail going out with the “mail sent on behalf of” tag that makes your email look really amateurish for people receiving your mail in outlook.