May 13, 2014 - rob

Configure sendmail to work with Gmail smtp relay

1. Check sendmail

Since gmail uses TLS, you will need to make sure your sendmail is compiled with TLS (for encryption) and SASL (for authentication). This is the command to use to check it:

/usr/sbin/sendmail -d0.1 -bv root

In my case, sendmail does have the necessary compilation flags so I was good. If yours doesn’t, you’ll need to re-compile sendmail and update the binary that is used to start the sendmail service, which is not covered here.

2. Upgrading Cyrus SASL

If your SASL installation doesn’t have the “plain” and “login” lib you will have authentication problem with Gmail. You can see why when you get to the sendmail configuration in the later steps. The common error in the /var/log/maillog is this:

AUTH=client, available mechanisms do not fulfill requirements

It was a vague error and I was so frustrated with it at one point I was ready to give up. However, this article about setting up Postfix with Gmail casted some light and helped me figured out the cause.

The problem is that SASL doesn’t have all the necessary plugins. The “login” and “plain” are the plugins necessary to talk to Gmail smtp. So I had to upgrade SASL to fix the problem. Here is what I did:

$ wget
$ tar -xzf cyrus-sasl-2.1.21.tar.gz
$ cd cyrus-sasl-2.1.21
$ ./configure
$ make
$ make install

$ mv /usr/lib/sasl2 /usr/lib/sasl2.orig
$ ln -s /usr/local/lib/sasl2 /usr/lib/sasl2

Note: if you have issue installing Cyrus SASL around compiling digestmd5.c, it’s because your compiler is too new. Read here to find out how to patch it.

Since I just switched out the old sasl2 lib without recompiling sendmail, I was concerned sendmail would poop during runtime. Luckily that didn’t happen. Dynamic lib rocks!

3. Generate SSL certificate

I made a directory called certs under /etc/mail. Here are the commands that I used to generate the SSL certificates.

openssl req -new -x509 -keyout cakey.pem -out cacert.pem -days 3650
openssl req -nodes -new -x509 -keyout sendmail.pem -out sendmail.pem -days 3650

Notice I made the certificates good for almost 10 years. I didn’t needed the cacert.pem to be exact.

I also copied /usr/share/ssl/ca-bundle.crt to /ect/mail/certs and included it in the sendmail configuration file. Other wise you’ll see some error like this:

unable to get local issuer certificate

The reason is that the ca bundle file has the Gmail certificate issuer. Although I read it somewhere that email still goes out with this error. Nonetheless, we don’t need to see this if we can fix it.

4. Configure sendmail

With the preparations above we are ready to configure sendmail. I found this tutorial very useful in terms of getting the correct sendmail configurations.

In summary, I have the /etc/mail/auth/client-info looks like this: “U:root” “” “P:password” “M:PLAIN” “U:root” “” “P:password” “M:PLAIN”

If you use Gmail hosted email with your own domain name, you will have username@hostname.tld in there.

Make sure run:

$ makemap -r hash client-info.db < client-info

and chmod 600 on client info files.

Essential lines in my

FEATURE(`authinfo’,`hash /etc/mail/auth/client-info.db’)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’)


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). – thanks Johnny for the suggestion.

The certificate files are generated/copied from the previous step. I’m no sendmail expert so the configuration lines may not be perfect. But it works. Let me know if you have better settings.

One tip I found very useful is to use the debugging feature. You can set a high log level in the to see at which step sendmail choked and for what reason.

Also, make sure run “make” or m4 every time you touch the

m4 >

So that’s pretty much it. I restart the sendmail service and out goes my email.


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