DOP 316: Bringing Back the Original Internet Vision Using Tailscale

Episode 316

Show Notes

#316: In this episode, Darin and Viktor speak with Avery Pennarun, CEO at Tailscale, on the evolving technology landscape, specifically focusing on the challenges and advancements in VPNs and connectivity. Avery discusses the limitations of traditional VPNs, the advantages of Tailscale’s unique approach to creating a secure virtual network, and the importance of maintaining a stable computing platform without compromising security. The episode delves into the historical context of networking, the philosophy behind Tailscale, its open-source client software, and detailed discussions on network security, trust issues, and the future of internet connectivity. This episode is a thought-provoking journey through the current state and the aspirational improvements in network technology and security.

Frequently Asked Questions

Is Tailscale a VPN?

Avery Pennarun calls that a great terrible way of putting it on DevOps Paradox episode 316, then separates two things sharing the name. The original VPN gave remote access to a private network you already had. What most people now mean is a service routing public traffic out through someone else’s link, which he suggests is closer to a virtual public network. Tailscale is the first kind.

Why does Tailscale add a layer in the middle rather than on top?

Avery Pennarun explains on DevOps Paradox episode 316 that the early internet let any device reach any device directly, and address exhaustion, firewalls and network translation broke that. Devices now talk to the cloud rather than to each other, which he compares to terminals and a mainframe. Tailscale inserts one layer at the internet layer so connections work again, stripping away decades of workarounds built for a network that stopped working.

Why does Tailscale support every version it has ever released?

Avery Pennarun says on DevOps Paradox episode 316 that the promise dates from the company’s founding, and covers roughly 89 builds per version across Linux distributions, phones, streaming boxes, routers, drones and embedded systems. His reasoning is operational: a device may sit powered off for three years and be switched on in an emergency, and requiring an update before it can reach the network defeats the point.

Why does software keep breaking underneath us?

Avery Pennarun argues on DevOps Paradox episode 316 that the industry lost its way when “we started believing that it’s better and easier to constantly shift the platform underneath us and then constantly run to keep up with the constantly shifting platform underneath us.” He points at security as the excuse: you cannot skip a patch, the patch breaks things, and everything downstream must move. He asks what changes if fixes simply do not break things.

Does a smaller network change your security requirements?

Avery Pennarun makes the case on DevOps Paradox episode 316 with a database he built for a computer store as a teenager, which he describes as riddled with holes that did not matter because it was not on the internet. Exposure to billions of people means even a vanishingly small fraction of attackers is a real one. Restrict access to the ten people who need it and the calculation changes entirely.

Do you have to trust Tailscale itself?

Avery Pennarun addresses this directly on DevOps Paradox episode 316. Each node generates its own key pair and the private key never leaves the device, so the company cannot decrypt traffic. The residual risk is being able to add a device to your network, which a feature called tailnet lock removes by requiring you to sign keys yourself. The clients are open source, and a self-hosted control plane exists.

What is the DevOps Paradox podcast?

DevOps Paradox is a weekly podcast co-hosted by Darin Pope and Viktor Farcic, covering DevOps, platform engineering, and modern software delivery. Episode 316 brings in Avery Pennarun of Tailscale to discuss what a VPN originally meant, why direct device-to-device connectivity stopped working, and how far a small trust boundary goes toward solving security. Every episode page carries the audio, the video, and a full transcript.

Episode Transcript

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Guests

Avery Pennarun

Avery Pennarun

Avery Pennarun is the Co-founder and CEO of Tailscale, a company revolutionizing secure networking with its zero-trust, easy-to-use approach. With a background in software engineering and an extensive career spanning innovative startups and tech giants like Google, Avery is recognized for his ability to simplify complex systems and foster technological innovation.

His work in network security, open-source software, and entrepreneurship reflects a commitment to creating solutions that prioritize usability and simplicity. Avery has contributed to widely-used tools like wvdial, bup, sshuttle, and more, illustrating his philosophy that great technology is both powerful and accessible.

A visionary leader with deep technical expertise, Avery is passionate about modern networking, open-source innovation, and helping organizations adapt to the demands of today’s dynamic digital landscape.

Hosts

Darin Pope

Darin Pope

Viktor Farcic

Viktor Farcic

Viktor Farcic is a member of the Google Developer Experts and Docker Captains groups, and published author.

His big passions are DevOps, Containers, Kubernetes, Microservices, Continuous Integration, Delivery and Deployment (CI/CD) and Test-Driven Development (TDD).

He often speaks at community gatherings and conferences.

He has published DevOps Paradox and Test-Driven Java Development.

His random thoughts and tutorials can be found in his blog The DevOps Toolkit.