Reply-To: gmail spam and Spamassassin

Over the last few months I’ve noticed huge increase is spam with a “Reply To:” field set to a gmail address. What the miscreants are doing is hijacking a legitimate mail server (usually a Microsoft one) and pumping out spam advertising a service of some kind. These missives only work if the mark is able to reply, and as even a Microsoft server will be locked down sooner or later, so they’ll never get the reply.

The reason for sending this way is, of course, spam from a legitimate mail server isn’t going to be blacklisted or blocked. SPF and other flags will be good. So these spams are likely to land in inboxes, and a few marks will reply based on the law of numbers.

To get the reply they’re using the email “Reply-To:” field, which will direct the reply to an alternative address – one which Google is happy to supply them for nothing.

The obvious way of detecting this would be to examine the Reply-To: field, and if it’s gmail whereas the original sender isn’t, flag it as highly suspect.

I was about to write a Spamassassin rule to do just this, when I discovered there is one already – and it’s always been there. The original idea came from Henrik Krohns in 2009, but it’s time has now definitely arrived. However, in a default install, it’s not enabled – and for a good reason (see later). The rule you want is FREEMAIL_FORGED_REPLYTO, and it’s found in 20_freemail.cf

Enabling FREEMAIL_FORGED_REPLYTO in Spamassassin

If you check 20_freemail.cf you’ll see the rules require Mail::SpamAssassin::Plugin::FreeMail, The FreeMail.pm plugin is part of the standard install, but it’s very likely disabled. To enable this (or any other plugin) edit the init.pre file in /usr/local/etc/mail/spamassassin/ Just add the following to the end of the file:

# Freemail checks
#
loadplugin Mail::SpamAssassin::Plugin::FreeMail FreeMail.pm 

You’ll then need to add a list of what you consider to be freemail accounts in your local.cf (/usr/local/etc/mail/spamassassin/local.cf). As an example:

freemail_domains aol.* gmail.* gmail.*.* outlook.com hotmail.* hotmail.*.*

Note the use of ‘*’ as a wildcard. ‘?’ matches a single character, but neither match a ‘.’. It’s not a regex! There’s also a local.cf setting “freemail_whitelist”, and other things documented in FreeMail.pm.

Then restart spamd (FreeBSD: service spamd restart) and you’re away. Except…

The problem with this Rule

If you look at 20_freemail.cf you’ll see the weighting is very low (currently 0.1). If this is such a good rule, why so little? The fact is that there’s a lot of spam appearing in this form, and it’s the best heuristic for detecting it, but it’s also going to lead to false positives in some cases.

Consider those silly “contact forms” beloved by PHP Web Developers. They send an email from a web server but with a “faked” reply address to the person filling in the form. This becomes indistinguishable from the heuristic used to spot the spammers.

If you know this is going to happen you can, of course add an exception. You can even have the web site use a local submission port and send it to a local mailbox without filtering. But in a commercial hosting environment this gets a bit complicated – you don’t know what Web Developers are doing. (How could you? They often don’t).

If you have control over your users, it’s probably safe to up the weighting. I’d say 3.0 is a good starting point. But it may be safer to leave it at 0.1 and examine the results for what would have been false positives.