While over 50-years-old, email is a technology that, in a lot of ways, works exactly as you’d expect. You open your iPhone’s Mail app or double-click your Outlook client, pick a recipient, write a message, and click “Send.” You almost never have to worry about it unless you get a new phone or your company switches servers; and even then, it’s just the quick headache of changing a few fields in the app.

From a technical standpoint, email is simple. But when we talk about mail, we don’t just mean the act of sending a message from one person to another. That’s the easy part. The complexity comes from the interlocking and overlapping steps and infrastructure, the trucks and sorting centers and package-sniffing dogs. With email, it’s just as complicated.

Conglomerates like Gmail and Outlook 365 do a disservice to mail server admins by making this system seem far less complicated than it actually is. And because it’s a simple technology – with plenty of free, open source solutions to whitelabel your own email service – lots of startups think this is a convenient way to gain passive income. We’ve definitely done our due diligence to help clients transition their mail servers, and are pretty up-front about how much (and how little) we know on the topic. And it’s because of that experience that we are also honest about not wanting to do that kind of work, if we can avoid it.

As part of our B Corp certification, we’re dedicated to supporting our local economy. We work with local email providers when possible. Unfortunately, the sort of hands-on approach provided by such companies isn’t always the right fit for every client. 

And even though we have qualms about giant companies (don’t worry: we’ll get to that in a minute), when clients ask us to help with their company’s mail server, we would rather point them towards Microsoft or Google instead of creating, maintaining, and charging for our own solution. That’s because, like most things on the internet, it’s far more complex than you expect, and to get down to why we recommend Microsoft and Google specifically, we have to start by understanding how email works.

Why’s It So Complicated?

Like the postal service, email is old, ubiquitous to everyday life, and incomprehensible for most. Personally, I love watching practiced people engage with complicated systems. I like it so much that, when I made a visually interesting video playlist to put in the background of my board gaming sessions, I included the short film “Reading and Sorting Mail Automatically” from the US Postal Service. Something is hypnotizing watching rollers shooting envelopes down conveyor belts while women with ’70s hair feed stacks of letters into green-screened computer cameras.

And that’s simply a small part of the process, which comes near the end of the lengthy chain of trucks, delivery folk, and post offices. Likewise, email has several parts, too, which go unnoticed until something stops working. And the only way to diagnose a complicated system is to run through each step one-by-one until you find the problem.

Step 1: Your Mail Client

Assuming you mail from home, you’ve probably got a mailbox, stationary, envelopes, stamps, and writing utensils. The digital equivalent packs all those things into your mail software. Whether it’s a standalone program – like Outlook – or a web-based solution – like Gmail – your mail client is the start of every letter’s digital journey.

While most website CPanels will offer an out-of-the-box solution so that you can send mail from an @YourCompanyName.com address, they’re often an afterthought with a clunky interface, like Horde, Roundcube, or SquirrelMail. While perfectly usable, most of us will type our username and server credentials into something like Microsoft Outlook, Apple Mail, or Spark.

Personally, I never liked the idea of downloading mail before I read it. This seems like a great way to get viruses and malware. Instead, I preferred browser-based options where all of the security was left to some Fortune 500 company’s mail server instead of my trial version of McAfee AntiVirus. In fact, I learned second-hand how that can happen when a previous boss ran out of his office yelling expletives because he’d fallen for a ransomware hack hidden within a Word .docx attachment. (Fortunately everything important was in his DropBox account and recovered with their premium file recovery service; but before we got it sorted out, he was legitimately considering buying Bitcoin for the hackers.)

Diagram showing how mail works, with a home mailbox, carrier, truck, and parcel basket.

Step 2: Your Mail Server

After the postal worker grabs your box, they check the postage, address information, and ask if it has hazardous materials before tossing it into their pouch. Then they take it to the post office, where it gets weighed, scanned, sniffed by dogs (I’m pretty sure this is accurate), and sent to the recipient’s post office where those postal workers can be relatively sure there aren’t undocumented hazards.

You may not realize it, but your outgoing mail server (aka your SMTP server) also examines your email to make sure it has all the requisite info. It even scans any attachments for viruses and might even glance at the email’s text for any potentially triggering words that could cause problems at its final destination.

To be fair, most outgoing mail servers aren’t as concerned with email content as the receiving server. For an example of what it might monitor, though, look at Gmail’s history: back in 2008, Gmail started a “digital breathalyzer” that asked you a series of math questions if you tried sending an email in the middle of the night. The idea is that, if you were drunk (or otherwise impaired), you’d fail the math problems, give up, and go to bed. Then, when you’ve had a full night of sleep (or as close to one as you can manage), you could soberly proofread (and possibly reconsider) your message.

Whether that’s part of Gmail’s servers or their web client is hard to say, since they’re so closely integrated. Point is, your mail server has the ability to read your messages. So, if privacy’s a concern, make sure those emails are encrypted.

Step 3: Their Mail Server

If you show up at a house unannounced, there’s no guarantee you’re going to get inside; but if you show up during the day, dress in a suit instead of a hoodie, and smile at the peephole (or, more likely, Ring cam), you’re more likely to get the door open.

Likewise, you don’t want the receiving mail server to think anything’s fishy. Make sure your server encrypts emails (with SSL or TLS), your DNS settings have SPF records for your SMTP server, and you’ve properly configured your domain’s DKIM entry.

Even with a clean shave and tailored suit, you’ll still raise eyebrows if you don’t also play the part. Email servers get just as easily spooked when they notice red flags, such as trigger words that can raise suspicions or SVG images in your signature (which are added as attachments and contain raw code.)

Because different orgs have different security needs, everyone’s mail servers will be watching out for different things. One company may get too many spam emails while another won’t even get submissions to their website’s contact form. That’s why we go through the slightly annoying (but hopefully charming) process of sending test emails which we request the receiver forwards back to us. This way, we can check any security warnings thrown into the email “header” (which is the digital equivalent of a letter’s return address and post office cancellation mark.) 

It’s shockingly common to find that emails received one month are suddenly blocked because the mail server got an update, and you were unaware because the notification for the update went to Spam. (Sometimes you just need to retrain those box-sniffing dogs.)

Step 4: Their Mail Client

Even if you make it past the bellhop, nothing can get you to Todd’s apartment if he locks the door and wears noise-canceling headphones while vacuuming. If someone sets up the strictest possible settings on their company Outlook app, you may have done everything possible and still had your email rejected.

Part of the problem with email is also what made it so popular: the simplicity. The same way you can avoid the post office by just handing Nana your Christmas card, there are countless programs to create an email server on practically any device with a microchip (and there are a lot of people creating mail servers for things like Nigerian prince scams.) As a result, the only way to guarantee your message gets to someone’s email address is to have them check. (After all, Grandma wants that canceled stamp for her collection.) It’s incredibly low-tech, considering most of the work we do, but sometimes that’s what’s needed. Like I said in my article about AI, there are some things computers just can’t do as well as humans. And we are humans, after all. (Pinky swear.)

Why Push Big Businesses?

As a certified B Corp, we are incentivized to promote local businesses when we can, so this article might seem like a contradiction. But as Whitman wrote in “Song of Myself“:

“Do I contradict myself?
“Very well then I contradict myself,
“(I am large, I contain multitudes.)”

One week I’m writing about the amazing uses that artificial intelligence has in my professional life, the next month I’m experimenting with Nightshade to “poison” language learning models from stealing photographers’ intellectual property. I can simultaneously write about how artists deserve proper respect while also mocking “bad” movies with my wife. This is not a justification for hypocrisy; it’s a celebration of nuance.

Like it or not, Google dominates the search engine business and has been consistently good at handling email. They’ve also ended so many projects that Killed by Google maintains a daily tally. We helped one client dive headfirst into Google’s AMP initiative only to find it silently abandoned by the goliath six years later. Heck, I even bought the already defunct Stadia controller to play approximately one hour of the X-Files-inspired Control on the family* iPad, so I am, by no means, a Google fanboy.And don’t even get me started on Microsoft, who single-handedly led one of the world’s largest consumer electronics recalls with the Xbox 360 and blazed trails for anti-competitive practices in the software industry. They also helped push browser-based email to the public forefront with the precursor to Gmail: Hotmail. (And as much as I’m still amazed they managed to stay in business after losing over a billion dollars with their Red Rings of Death, I treasure my experiences on the 360 with Guitar Hero and Rock Band, leading to an unfortunate and embarrassing karaoke phase.)


Point is, I am fully aware that our society is built in a way that prevents me from being able to conscientiously vote with my dollar in every single scenario. As much as I may oppose a certain children’s author’s bigoted viewpoints, I still can’t help my child from learning about, and wanting to watch, popular films based on those works. This is the same world where, after I watched hours of documentaries about a famous YouTuber who swindled thousands of people out of their money, my kid asks to get a sports drink founded by this provocateur.

When people want an email solution, Google Workspace (formerly G Suite) is the first thing I recommend, but with the caveat that they may very likely sell that feature just like they did their domain registration business. If that concerns you, I will then explain how Microsoft isn’t likely to go anywhere because they’ve spent a large chunk of time and money buying and subsequently killing their competitors.

If the alternative weren’t a huge headache with little promise of security and a self-hosted infrastructure requiring a full-time systems administrator (which would decimate any business’ budget), I honestly wouldn’t recommend either of them. Since email is usually an afterthought, it’s not the most efficient use of energy for taking an ethical stance. If the option is to force a client to burn dozens of hours on a communications platform or to use Google while simultaneously making monthly donations to ethical causes, I won’t hesitate copying a link to Gmail.

So keep in mind that when we offer a big business, out-of-the-box, anti-competitive, potentially ethereal solution, we’ve spent hours debating that decision. And if you want the full story, buy me a latte (preferably at the local coffee shop) and I’ll untangle the details.

(Accompanying images by Caleb Costelle.)

*Anyone with a pre-adolescent child knows that the family’s iPad quickly becomes the child’s iPad. Thank you, Crayola Create & Play, for turning our $800 tablet into a virtual finger paint set with smiling amphibians.

Bronson Portrait Yellow 320x346

Bronson O’Quinn is Mediocre’s Lead Developer. He gets excited when the Post Office announces their new stamps. He also wants it known that he’s been using GMail since he socially engineered his way into the closed beta back in 2004, registering the now-embarrassing account name “g00gl3.h4ck3r”.


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