The Looming Shadow Over Tailscale: Another Tech Service at the Crossroads
The tech world is buzzing with news of Tailscale’s latest funding round, and my notification feeds are lighting up with concerned users discussing what this might mean for the future of the service. Sitting here in my home office, watching the autumn leaves fall outside my window, I can’t help but feel a familiar sense of dread.
Remember when Reddit was just a gathering place for communities? Or when LastPass was the password manager everyone recommended? The pattern is dishearteningly familiar - a beloved service gains popularity, attracts investor attention, and then begins the slow descent into what’s now termed “enshittification.” It’s like watching a slow-motion train wreck, and many of us in the self-hosted community are bracing for impact.
Tailscale has been brilliant - it’s the kind of tool that just works. Even my daughter managed to set it up on her devices without any help from her tech-savvy dad. But this latest funding round has triggered alarm bells throughout the self-hosted community, and honestly, they’re not wrong to be concerned.
The self-hosted community is already mobilizing, sharing alternatives like NetBird, Headscale, and ZeroTier. Some users are even returning to bare Wireguard configurations. While these alternatives might require more technical expertise, they offer something invaluable: control over our own infrastructure.
Last weekend, I spent several hours testing Headscale on my home server. While it doesn’t have Tailscale’s polished interface, it works surprisingly well. The setup process reminded me of the early days of running my own mail server - a bit fiddly, but ultimately rewarding. The beauty of self-hosted solutions is that they can’t be taken away from us by a board meeting in Silicon Valley.
The frustrating part isn’t just the potential loss of another great service - it’s watching history repeat itself. Every time we build our infrastructure around a “free” service, we’re essentially building our house on rented land. The landlord might be friendly now, but eventually, they’ll want to increase the rent.
Looking at the broader picture, this situation perfectly illustrates why the self-hosted movement continues to grow. It’s not just about saving money or being technically curious - it’s about maintaining autonomy in an increasingly centralized digital world. Every time a service goes through this cycle, more people join our community, seeking alternatives they can control.
Right now, Tailscale still works brilliantly, and nothing has actually changed. But perhaps that’s exactly the right time to start planning alternatives. The self-hosted community has always been about being proactive rather than reactive, and this situation is no different.
For those feeling anxious about potential changes, remember that we’ve been here before, and we’ll be here again. The beauty of open-source software and self-hosted solutions is that they give us options. They might not always be as polished or convenient, but they’re ours to control.
The next few months will be interesting to watch. Whether Tailscale follows the familiar path of enshittification or breaks the mold, the self-hosted community will continue to grow and adapt. That’s the real power of this movement - we’re not dependent on any single service or company. We’re building something more resilient, one self-hosted service at a time.