The Email Server Saga: Why Big Tech Has Us in a Chokehold
The other day, while setting up a new development environment for work, I stumbled across an interesting discussion about self-hosting email servers. It brought back memories of my own attempts at email independence over the years, and the subsequent frustrations that followed.
Running your own email server used to be a badge of honor in the tech community. Back in the late 90s and early 2000s, it was almost a rite of passage for system administrators and tech enthusiasts. The technical challenges were significant but manageable - configuring Sendmail or Postfix, setting up spam filters, and maintaining proper DNS records.
But today? The game has completely changed, and not for the better. The real challenge isn’t the technical setup - it’s playing nice with the email gatekeepers. Google, Microsoft, and other major providers have effectively created a oligopoly over email delivery. They’ve established themselves as the arbiters of what constitutes “legitimate” email, often with arbitrary and opaque rules.
Reading through various experiences shared online, it’s clear that even perfectly configured servers with all the right protocols - SPF, DKIM, DMARC, you name it - can still fall victim to mysterious delivery issues. One particularly frustrating story involved someone’s entire IP range getting blacklisted despite following every best practice in the book.
This hits close to home. During my last attempt at email independence in 2019, I spent countless hours troubleshooting why my perfectly legitimate emails were landing in spam folders or disappearing into the void. The breaking point came when my daughter’s university application emails weren’t getting through because our domain was deemed “suspicious” by Microsoft’s automated systems.
The irony isn’t lost on me that while legitimate self-hosted email servers struggle to deliver mail, my inbox is still flooded with spam that somehow makes it through Gmail’s supposedly sophisticated filters. It feels like the big players are more interested in maintaining their market dominance than actually solving the spam problem.
Many have suggested using SMTP relay services as a workaround, but let’s be honest - that’s just paying tribute to the same system we’re trying to break free from. It’s a band-aid solution that further legitimizes the current power structure.
Looking at the broader picture, this email server situation is a perfect microcosm of what’s happening across the tech landscape. The internet was built on principles of decentralization and open protocols, but we’re witnessing the steady erosion of these ideals in favor of centralized control by a handful of tech giants.
The solution isn’t giving up - it’s pushing back. We need more voices advocating for email infrastructure reform, more pressure on big providers to be transparent about their filtering criteria, and continued support for projects working to make email hosting accessible to everyone.
Maybe the next time I feel the urge to set up my own email server, the landscape will have changed. Until then, I’ll keep supporting initiatives that promote digital independence and following the efforts of those brave souls still fighting the good fight in the email hosting trenches.
For now, though, I’ll stick to my current email provider while focusing my self-hosting energy on services where I actually have a fighting chance at independence. Sometimes you have to pick your battles, and this is one where the deck is simply stacked too high against us.