Easy delivery with mstmp and GMail

MTA solutions sendmail, postfix or qmail all seem to be overkill. I want to take the simple course (basically because I’m lazy). Fortunately, there are a variety of simple SMTP relays out there such as ssmtp and esmtp. Some network officianatos may consider this to be re-inventing the wheel, but then again, I’m sure glad that my car doesn’t roll on stone cylinders.

After some consideration, I chose to go with msmtp. I like its flexible configuration, and it’s just the right size for the job (with room to grow). The major thing I was looking for was STARTTLS support. I wasn’t so concerned with the trust files and certificates, I just had a need to support GMail’s minimum requirements. Yes, msmtp gives you that and the whole 9 yards, for when I need them all.

msmtp Configuration for GMail

With a combination of their official configuration example plus a few targeted suggestions from Grey Bearded Geek’s take at ssmtp, I came up with the following:

# Set default values for all following accounts. defaults host smtp.gmail.com port 587 timeout off protocol smtp domain localhost # /usr/bin/msmtp --version # plain cram-md5 digest-md5 gssapi external login ntlm auth on user GMAIL-USER password GMAIL-PASSWD tls on tls_starttls on # WARNING: When the checks are disabled, TLS/SSL sessions will be vulnerable to man-in-the-middle attacks tls_certcheck off logfile /var/log/msmtp.log ###syslog on # A system wide configuration is optional. # If it exists, it usually defines a default account. # This allows msmtp to be used like /usr/sbin/sendmail. account default # Construct envelope-from addresses of the form "user@oursite.example". ###auto_from on from USER@DOMAIN maildomain DOMAIN

You plop in the GMAIL-USER and GMAIL-PASSWD, and you’re good to go.

Custom From: Address

I soon learned that the from and maildomain settings are irrelevant; Google will not arbitrarily change the From: header of your mail. That makes sense. So the mail will appear as if it’s coming from you, personally. Well, it turns out that there’s a few things you can do to get around that.

Create yourself a dedicated GMail account. Now you have isolated your soon-to-be-wildly-popular start-up’s e-mail account from your personal one.
Follow the instructions on adding a custom From: address to your account. I had to use the older version of the GMail interface to do so. Google will verify that you own the address – you’d better be able to receive mail at that address – and then you can make it your default.

GMail will now send your mail as it were coming from that address, but it will do so without providing an alias.

When sending your outbound mail, you can include the following headers:

From:  ALIAS
Reply-To:  ALIAS <USER@DOMAIN>

Google will respect the ALIAS portion of the From: address, though not the address itself. The Reply-To: is optional, but respected in its entirety (alias and address).

Works like a charm.

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