Delivering Automated Transactional E-mail

A ClickZ subscription confirmation e-mail recently wound up in a subscriber’s spam folder. Regrettably, this is an all too common situation.

A few years ago, there was no problem getting automated, transactional messages delivered directly from the server that generated them. Volume was low enough and ISP delivery requirements relaxed enough that e-mail got through. There was no need for authentication, whitelisting, or feedback loop registration. Often, delivery was even possible without reverse DNS (define) entries or MX (define) records for response e-mail.

Three things occurred that changed this situation. The first, as I explained last month, is that across-the-board requirements for successful e-mail delivery are getting stricter as ISPs fight to keep spam out of user inboxes. The second is the increasing use of botnets (define) for spam, where many machines send only a small amount of spam each. This means low-delivery rates no longer get a free pass from ISPs. Finally, widespread abuse of Web forms, CGI (define) scripts, and unsecured servers mean many spam-filtering systems now view autogenerated messages with extra suspicion.

Many organizations put a significant amount of effort into managing e-mail marketing campaigns. They monitor, analyze, and track deliverability and negative and positive response data and work hard to ensure lists are properly managed and campaigns are effective. Transactional messages generated for customer service, sales, product support, subscription confirmation, and so forth often come from a variety of sources within an organization and slip under the organizational radar. This is unfortunate, as it means they often don’t get the same level of analysis and support even though they’re often some of the most important e-mail a company generates.

Failure to follow up on a sales inquiry or customer service request can directly lead to lost revenue. Failure to deliver subscription confirmation requests leads to smaller lists. Failure to deliver subscription notifications can lead to increased complaints and delivery problems for subsequent marketing messages.

The difficulty in most large organizations is political. Transactional messages are often generated by disparate parts of the organization, each of which doesn’t wish to surrender control of what it views as essential pieces of their operation. Fortunately, there are steps you can take to address these issues.


Determine what e-mail is sent, what the purpose of each is, and what part of the organization sends it.

Common e-mail sources include:

  • Subscription confirmations/notifications
  • Customer service inquiry responses
  • Sales messages


Determine how well the messages are managed. The simplest approach is to generate and analyze each message type. This should be done from technical, compliance, and messaging perspectives. The same analyses you apply to bulk marketing messages in regard to RFC (define) compliance, authentication, bounce and response handling, and permission management apply to most transactional messages.

Having clear data in hand that demonstrates delivery, legal, or corporate compliance issues is the strongest argument for intervention.

Centralize Delivery

Having many different systems sending e-mail from different sources and with different configurations is a substantial management headache. Yet it’s important that different units are able to generate the e-mail they require. Centralize e-mail delivery without necessarily centralizing e-mail generation. This can be achieved in numerous ways, including using an e-mail smart host, routing transactional messages, and standardizing on an API (define) for sending from a single system.

You’ll probably wish to keep transactional and bulk e-mail separate, but by having all transactional messages go through a single source with consistent authentication, whitelisting, effective bounce processing, and subscription management, you’ll have a much clearer handle on what is and isn’t delivered. It will be possible to both identify and resolve delivery issues before they affect your business.


As you would with any bulk mail server, ensure your transactional servers are registered on ISP whitelists and feedback loops. Monitor what’s going out, what’s coming back in, and how the e-mail is received at major ISPs. In short, treat your transactional e-mail servers the same way you do your marketing servers.

Given transactional messages’ importance and the increasing frequency with which they’re blocked, they deserve at least as much attention as bulk e-mail. Centralize delivery, then apply the same principles and techniques as you do to marketing campaigns to ensure transactional messages are delivered every time.

Until next time,


Want more e-mail marketing information? ClickZ E-Mail Reference is an archive of all our e-mail columns, organized by topic.

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