Email sucks

I've recently gone through the process of migrating from Proton Mail and related services to Office 365. Proton is a fantastic service with a focus on privacy, but real time 2 way syncing of calendars across services is not on the feature set. I've been meaning to make this change for awhile. It certainly carries a level of reluctance, as I'm no fan of Microsoft.

Once upon a time

There was a time not all that long ago that you could easily spin up your own mail server. Every cheap web hosting company began the race to provide cPanel management and built-in emailing capabilities. Get a plan, point your domain, and start sending!

I won't go into the nitty-gritty history of email, as that's been covered to death across the internet. I will, however, point out the naivety of the time. The easier it is for regular people to maintain an email server - the easier it is for the most malicious and spammy among us to do the same.

New Barriers to Entry

We've grown a lot since those early days, implementing new email authentication protocols such as SPF (Sender Policy Framework), DKIM (Domain-keys Identified Mail), and DMARC (Domain-based Message Authentication, Reporting, and Conformance).

Each new layer of authentication helps prevent spoofing and malicious use at the cost of just one more setup step. If you don't want to go straight into the void - or worse, a spam folder - you'd almost certainly want to triple check that you haven't missed any authentication records.

Let's say you've put in the leg work to set up a new email on your domain. The next issue you have to wade through is the social credit score collectively known as the "trusted sender rating". Using this system, your email server gets judged on how well known it already is, how often you email, and other criteria. Hungry email blacklists waited for these low hanging fruit examples like sharks in the water, devouring everything they could to prove they were the most robust blacklist in the industry.

Like much of the web, running an email became, well, complicated. Keeping up with the demands of the technology - both the security and the social credit scoring - began to take a larger and larger toll. On shared hosting, if one tenant did something bad, every other tenant on that cluster would be impacted as the IP address of the server would end up on a blacklist. Even basic newsletters looked like spam from a quantity perspective, and "better to be safe than sorry" stopped many domains from emailing before they could begin. Unless, of course, you were in the cool kids club.

Technology Capture

Companies like Google with Gmail, or Microsoft with their Outlook/Exchange offerings stepped in. If the problems were out-scaling business's ability to solve them, then leaning on a company that could operate at that scale was the only path that made sense.

Back then, it seemed simple. I recall getting an early invite to Gmail (beta). I stayed on Gmail for over a decade. I didn't have to manage DNS records. I didn't have to wake up at 3am because an email server was offline at the office. I was for all intents and purposes free. We all had a consistent web UI to check our emails and that was that.

Everyone was so relieved from the Google/Microsoft takeover of email that we grew complacent. We began to rely on them. We forgot how to run email servers, because we didn't need to do that anymore. For a time, that was fine. We didn't see the problems that we were creating by outsourcing our solutions to big tech.

Now, in 2025, we see the price we pay. Running a custom domain on email and outsourcing the maintenance for it will cost you. An ever growing monthly subscription sits like a weed in the garden. Year over year the costs grow a little more.

Concerns over privacy are at an all time high, as Microsoft has begun collecting data on users who choose to leverage the new Outlook. To further ensure you are on this new privacy violating advertisement system, they have opted to kill the perfectly fine existing mail and calendar applications. On the exchange side, they disable SMTP login credentials and implement complex API subsystems instead - which makes checking your email from any standards-compliant client a problem. Microsoft wants to advertise to you and gain information about you. For that, they need you in their walled garden.

What choice do you really have now? You could go back to hosting your own emails, but again - you aren't a part of the cool kids club. You don't have the fancy Microsoft varsity jacket or the Google shoes. You're just some nobody. That's how they'll see your emails, too. Enjoy the spam folder, nobody.

Island of Misfit Email Clients

It all started with a simple transmission of text data from one computer on a network to another. a simple SENDMSG call, and a simple text file. As users began to demand more, standards arose to support more. POP and IMAP. With these standards, a gold rush of email clients emerged. Everything from web based mail to Thunderbird. Microsoft joined in with their Outlook software, which added an insane amount of functionality on top. No matter which operating system you were on, there were options.

The Microsoft and Google takeover we enabled fractured this once thriving ecosystem. Instead of increasing the proficiency of the existing standards, these companies worked to further isolate themselves from the standards. You could no longer use IMAP/POP and have it "just work". No, now email clients needed to carefully craft integrations with each service independantly. They want your data, and they are going to get it.

What we're left with is a buggy pile of software that sits taller than any skyscraper. I've tried them all - Mailbird, Thunderbird, Betterbird, Postbox, EMClient, Spark, Canary, etc. I could name a list longer than this article itself. Every single last one of them have platform-specific issues that are hard to maintain and solve for. Where you used to be able to follow the standard spec and rest easy, now you need to develop several email applications in one with a shared UI to support the same services that used to play by the rules. A Frankenstein of puzzle pieces that ends up looking more like soup than software.

Now, this software space is saturated with messy code bases and user subscriptions just to try to keep up. There are no good email clients left. When you consider that people are willing to pay $25/month minimum for the subscription based email client Superhuman, its easy to see that things have gone horribly wrong.

Living In The 90's

While we've been pushing email more and more into the monopoly controlled, subscription based, privacy invading corners of the world, the underlying technology hasn't moved much.

The web has grown a lot since email was born. We have new HTML semantics. We have new CSS capabilities and design paradigms. We can now render infinitely complex layouts and we have the tools to help us.

But not email.

Email is still stuck in the old days. CSS v2 released back in 1998 is the "cutting-edge" of design here. Microsoft's own Outlook used the Word rendering engine instead of a web renderer! This means that designing an email requires arcane, lost knowledge of how the web used to work. Table layouts. Platform specific hacks.

Entire businesses have formed around the art of making emails look the same on all clients - a task too large for any single developer. The only thing you can do here is limit your expectations on what is possible in email, or outsource it all for another bid on your ever shrinking revenue.

Closing Thoughts

Maybe if we weren't so caught up in collecting user data, impressing investors, and infinitely scaling our monopolies through increasing monthly subscriptions, the low hanging fruit of "making it better" would have been given a cursory glance.

As it stands, though, email just sucks.

At least we're all focusing on the important things now, like adding AI that nobody wants and paying for it with the customer's money.