Illustrations by Kenny Miesner
The system used to send an email from your inbox to your customer’s inbox—the rules, instructions, process—was standardized in 1982. The World Wide Web was created in 1989. I’ll let that sink in a bit. The process used to send email is older than almost everything you’re using to read this blog post. It’s older than responsive web design, smartphones, camera phones, Facebook, WordPress, flash drives/thumb drives, text messaging, Google, the author of this post, publicly available dial-up, web browsers, HTML, the World Wide Web, and the Macintosh computer. Email is older than the very industry Webspec is a part of. While the email process was revised in 2008—about a year after the release of the first iPhone—it still functions like it did in 1982. In the tech world, email is ancient, and its age shows.
When a potential customer fills out a contact form on your site, you receive an email with their information. You then send a reply to this customer and they receive it in their inbox rather quickly, instantly, almost. This is the preferred experience we’d like for our clients to have. This is the preferred experience that you and your customers would like to have. To keep the email out of your spam folder, to contain everything that you sent (and not more or less), to reach the recipient quickly, and to even send at all, are things that we take for granted. At Webspec, where we manage website emails for over 200 clients, we know better than to take the smooth experience for granted. Over the course of our 16 years in business, we’ve learned that email is not instantaneous, synchronous, or guaranteed to reach your recipient. Email is a multi-step process involving a new third party every step of the way; within each step something can go wrong, and we’ve definitely seen it go wrong. Instead of giving up though, we’ve used our knowledge to prevent and deal with potential issues that may arise, the specifics of which will be covered later in this post.
What does it mean, though, when I say that email is a multi-step process, or that it involves a new third party every step of the way? After all, you just hit the send button in your email client and it appears in your recipient’s inbox, right? It can’t be that complicated.
It is complicated though, and while I don’t expect anyone to know the entire process, it is important to demonstrate what can go wrong and what we do to prevent it from happening. The best way to explain how email works is to use an analogy. Let’s imagine that sending an email was like sending a letter.
The journey begins after the letter has been addressed and stamped and is ready to be sent. The first part of the email sending process starts here. Someone has to be told that the letter needs to be sent. You could do this in multiple ways, such as walking it out to your mailbox and lifting up the flag, placing it at the front desk in your office where the mail person will pick it up, or driving it to the post office and placing it in their outbox. While this may seem like a straightforward task where nothing can go wrong, we are already assuming that this step will happen successfully. In the tech world, we have a law, Murphy’s Law, that states, “Anything that can go wrong, will go wrong.” In managing client’s emails we’ve seen problems during this step. You could trip and fall on the way to the mailbox, the neighbors could have hit your mailbox and knocked it over, you could have forgotten to lift the flag up, the flag could have been blown down in the wind. It could be a federal holiday, the letter could slip out of your hands and fly away. Your car could break down on the way to the post office, the post office could be closed, the mail person could forget to visit your building, someone could accidentally throw away your stack of letters, etc. In the end, your letter is not sent as you expected.
When talking about email, problems during this step could be forgetting your login info, typing the recipient’s address wrong, forgetting to set the recipient entirely, attaching too many photos, or losing your internet connection before you were about to hit send. While all minor problems, applying Murphy’s Law means if any of these possibilities could happen, they will eventually happen. This will result in your message not being sent.
If something happens during this first step—telling someone that the letter needs to be sent—it’s straightforward to do something about it. First, it’s easy for you to realize that something went wrong. After all, you were there when that letter slipped out of your hands and was carried away by the wind. You were there to spot that the mail person missed your letter when picking the rest up. With email, problems at this step are easy to spot, because your email client will alert you if something went wrong, and to fix the issue, you can adjust and try again.
Now that the letter has been successfully picked up by the postal service, it’s up to them to get the letter where it needs to go. Here’s where the third parties that were mentioned earlier come into play. Once your letter has been picked up, what happens to that letter is no longer in your control—or your website company’s control. That loss of control can be a very scary thought, but it isn’t something that people typically consider when they think about email. With a letter, the post office doesn’t simply take your message, drive directly to the recipient, and place it in their mailbox; email doesn’t work that way either. Letters get driven to regional distribution centers, may be loaded onto different trucks or airplanes, get sent to local post offices, get loaded into your route’s truck, and then are finally delivered to your recipient’s inbox. The further away you are from your recipient the longer the process becomes, with the addition of more steps. That’s true with letters, email, Amazon packages, and the Internet in general. There are multiple people (services) handling your email at this point, so that introduces opportunities for even more problems.
Let’s apply Murphy’s Law to the above process and think about some things that can, and will, go wrong with sending this letter. The mail truck could get into a wreck on the highway and the letter could be lost. Your mail person could be greedy and steal the letter because it contained money, the sorting machine could break down, there could be a fire at a facility and the letter suffers damage, a funding bill could shut down the entire service. All of the workers could go on strike, the letter could be left in the back of the truck, the airplane could run out of gas and have to make an emergency landing, the letter could get sent to the wrong facility.
Like a letter, email will exchange many hands from your mailbox to the recipient’s. When sending email, a simplified path it will take may look like Your Computer->Local ISP->Regional ISP->National/Worldwide ISP->Customer’s Regional ISP->Customer’s Local ISP->Customer’s Email Server->Customer’s Computer. At all of these handoffs delays can (and eventually will) arise. The local ISP may have a firewall that blocks your message (without ever telling you), the national ISP may deem that your local ISP has sent too many messages and will hold off sending yours for a day, or even delete it (once again, without telling you). The email may reach all the way to the customer’s email server, but they were having a short period of downtime and rejected your message.
In many of these scenarios, you will never know that a problem happened, or that it happened to your letter specifically. All you know is that you successfully handed your letter to the mail carrier. You think that your recipient will get the letter, but all they see is that it never hit their inbox. Because you weren’t the one physically delivering the letter directly to your recipient’s mailbox, there is nothing you could do to prevent these scenarios from happening.
However, there are some scenarios during this step where you will be notified if things go wrong, both when sending a letter or an email. If you fail to pay the right postage or get the address wrong, then your letter will be returned to you. This also happens when sending email—type in an invalid email address and your email client will happily send you a message to have you try again. What’s to notice here is that you have control over this process. You’re the one that forgot to add the stamp, you’re the one that misspelled the address. In these cases the problem arose from actions within your control, and you’re able to fix the mistake and try again. It’s the problems you don’t have control over, the problems that arise out of the actions of others, those third parties, that cause the most anxiety and headaches.
Let’s assume that the letter successfully made it to your recipient’s mailbox. It’s time to celebrate! That reply to their quote request finally made it to their valued inbox. Then their mailbox gets hit by a car and all of the letters fall out. Then their nosy neighbor pulls out the letter and walks away with it. Then the recipient drops it on the way to their house and it falls in a puddle, their dog eats it, they accidently throw it away without realizing it, it looks like junk mail so they shred it, their supervisor thought it looked like junk mail so they shred it. Their mailbox gets struck by lightning and all the letters catch fire, or a tornado hits. All of these are unlikely, but remember Murphy’s Law: if anything can go wrong, it will go wrong. In some of these scenarios, like a dog eating the letter, the recipient will know something went wrong and will be able to deal with it. But what about if their manager or neighbor steals the letter from them? What if it got stuck to the back of a different letter they accidentally threw it away? Will they ever know that you took the time to respond to them?
While some of the above scenarios may seem silly, in email terms, problems during this step are common, and most people don’t know that they have systems in place that increase the likelihood of something going wrong. Those systems are called firewalls and spam filters. Webspec has seen spam filters delete emails without notifying anyone. Webspec has seen firewalls think that the email was too long and delete the message, again, without telling anyone. In an example that comes to mind, I’ve seen a firewall act like it didn’t like the design of the return address sticker placed on the envelope (the return address sticker was blue, and its favorite color was red) and delete the message without telling anyone.
We see that the actions of others—third parties—are affecting the deliverability of your letters and your email. In many cases problems arise without any alerts that something went wrong. How then, can you be notified if there was a problem and your letter didn’t get to its destination? The same way you can add tracking to your UPS packages, you can add tracking to your emails.
Webspec adds tracking to our client’s emails when they are sent from the website itself (not for emails sent from your inbox). That way when your customer submits contact forms, job applications, or lead generation forms, we can see when problems arise while sending the notification to your inbox. We are able to identify problems that you might not have been notified of until now. The specific service we use to track website emails is called Mailgun. Mailgun is able to provide notification if an email doesn’t reach the recipient’s inbox. In our letter analogy, Mailgun is able to alert us if there’s a problem up until it is successfully placed in the recipient’s mailbox. What was previously a mystery can now be tracked. If the mail truck got into a wreck on the highway and all the letters were lost, for example, we’d know that it happened to your letter specifically.
Mailgun also provides its own set of tools to help your messages reach your customers, the specifics of which are pretty technical, so I’ll defer to the analogy. Mailgun makes your letter look more official so it’s less likely to be treated as junk and end up in the trash accidentally. It also sends the letter using mail routes that receive more resources and funding so the letter is more likely to reach its destination on time.
But tracking only tells you if there’s a problem, and tools to prevent problems can only go so far. Take the scenario of the letter successfully reaching your recipient’s mailbox, but their guard dog pulls out the letter and rips it to shreds (your client’s spam filter deletes the message) without anyone knowing. When problems like those arise, Webspec can take the tracking in Mailgun and work with your IT department to get the problem addressed, which is not something that’s possible with physical letters.
When a letter is sent through the mail it travels across the country, switching hands and going through different systems. At each step of the process something could go wrong, and using Murphy’s Law, we expect that things will go wrong. But that’s the nature of physically sending a letter over a long distance. Email works much in the same way, and offers just as much opportunity for problems to arise. An email message doesn’t just go from your inbox to your customer’s. It travels through a vast array of third parties, all of which have their own rules and systems, many of which are antiquated. That doesn’t mean we can’t do anything about it. We use tools to prevent problems, implement tracking to help diagnose, and work with your IT department to resolve the remaining issues. The next time an email you send to a customer arrives in their inbox instantaneously, remember that it’s a feat worth celebrating. Happy emailing.