Some thoughts on best practices for SMTP blocking of e-mail spam

Blocking e-mail spam at the time of SMTP (Simple Mail Transfer Protocol) transfer has become a best practice. There is no point wasting precious bandwidth & disk space and spending time browsing a huge spambox when most of the incoming flow is clearly spam. At LinuxForce our e-mail hygiene service, LinuxForceMail, makes extensive use of SMTP blocking techniques (using free and open source software such as Exim, Clam AV, SpamAssassin and Policyd-weight). But we are extremely careful to only block sites and e-mails that are so “spammy” that we are justified in blocking it. That doesn’t prevent false positives, but it keeps them to a minimum.

Recently we investigated an incident where one of our users had their e-mail blocked by another company’s anti-spam system. In investigating the problem, we learned that some vendors support an option to block e-mail whose Received header is on a blacklist (in our case it was Barracuda, but other vendors are also guilty). Let me be blunt: this is boneheaded, but the reason is subtle so I can understand how the mistake might be made.

First, blocking senders appearing on a blacklist at SMTP time is good practice. But to understand why blocking Received headers at SMTP time is bad, it is important to understand how e-mail transport works. The sending system opens a TCP/IP connection from a particular IP address. That IP address should be checked against blacklists. And other tests on the envelope can help identify spam. But the message headers including the Received header are not so definite. We shall see that even a blacklisted IP in these headers may be legitimate. So blocking such e-mail incurs unnecessary risks.

The problem occurs when a user of an ISP (Internet Service Provider) sends an e-mail from home, they are typically using a transient, “dynamic” IP address. Indeed it is possible that their IP address has just changed. Since the new address may have been previously used by someone infected with a virus sending out spam, this “new” IP address may be on the blacklists. So, due to no fault of your own, you have a blacklisted IP address (I will suppress my urge to rant for IPv6 when everyone can finally have their own IP address and be responsible for its security).

Now, when you send an e-mail through your ISP’s mail server, it records your (blacklisted) IP as the first Received header. So your (presumably secure) system sending a legitimate message through your ISP’s legitimate, authenticating mail server is blacklisted by your recipients’ overambitious anti-spam system. Ouch. That is why blocking such an e-mail is just wrong. This kind of blocking creates annoying unnecessary complications for the users and admins at both sides. Using e-mail filtering to put such e-mails into a spam folder would be a reasonable way to handle the situation. Filtering is able to handle false positives whereas blocking generates unrecoverable errors.

Do not block e-mail based on the Received header!

Posted by CJ Fearnley in Security, Systems Management, Tech Notes, Ubuntu, 0 comments

A FOSS Perspective On Richard Schaeffer’s Three Tactics For Computer Security

Federal Computer Week published a great, succinct quote from Richard Schaeffer Jr., the NSA’s (National Security Agency) information assurance director, on three approaches that are effective in protecting systems from security attacks:

We believe that if one institutes best practices, proper configurations
[and] good network monitoring that a system ought to be able to
withstand about 80 percent of the commonly known attack mechanisms
against systems today, Schaeffer said in his testimony. You can
actually harden your network environment to raise the bar such that
the adversary has to resort to much, much more sophisticated means,
thereby raising the risk of detection.”

Taking Schaeffer’s three tactics as our lead, here is a FOSS perspective on these protection mechanisms:

Best practices implies community effort: discussing, sharing and collectively building understanding and techniques for managing systems and their software components. FOSS (Free and Open Source Software) communities develop, discuss and share these best practices in their project support and development forums. Debian’s package management system implements some of these best practices in the operating system itself thereby allowing users who do not participate in the development and support communities to realize the benefits of best practices without understanding or even knowing that they exist. This is one of the important benefits of policy- and package-based operating systems like Debian and Ubuntu.

Proper configuration is the tactical implementation of best practices. Audit is a critical element here. Debian packages can use their postinst scripts (which are run after a package is installed, upgraded, or re-installed) to audit and sometimes even automatically fix configuration problems. Right now, attentive, diligent systems administrators, i.e., human beings, are required to ensure proper configuration as no vendor — not even Debian — has managed to automate the validation let alone automatically fix bad configurations. I think this is an area where the FOSS community can lead by considering and adopting innovations for ensuring proper configuration of software.

Good network monitoring invokes the discipline of knowing what services are running and investigating when service interruptions occur. Monitoring can contribute to configuration auditing and can help focus one’s efforts on any best practices that should be considered. That is, monitoring helps by engaging critical thinking and building a tactile awareness of the network — what it does and what is exposed to the activities of a frequently malicious Internet. So, like proper configurations, monitoring requires diligent, attentive systems administrators to maintain security. LinuxForce’s Remote Responder services builds best practices around three essential FOSS tools for good network monitoring: Nagios, Munin, and Logcheck.

Posted by CJ Fearnley in Security, Systems Management, 0 comments