Tailscale Headlines

XDA Developers

Article in which a user describes their experience configuring Tailscale in order to use Jellyfin.

Companies:Tailscale

BetaKit

Tailscale announced its first-ever acquisition, purchasing Vancouver-based privileged access management (PAM) startup Border0 and absorbing its entire seven-person team. The deal adds protocol-aware controls, session visibility, and approval workflows to Tailscale's platform, accelerating its move into enterprise PAM.

Companies:Tailscale

The Globe and Mail

The Globe and Mail profiles Tailscale as one of Canada's fastest-growing tech companies, reporting that revenue has grown at an accelerating rate in 2025 and that the company has become the VPN provider of choice for AI companies, with paid customers reaching 20,000 and over one million active monthly users.

Companies:Tailscale

BetaKit

Tailscale CEO Avery Pennarun warns that companies rushing to adopt AI and deploy Model Context Protocol (MCP) servers are bypassing fundamental security practices, creating a chaotic environment for corporate cybersecurity. He argues that Tailscale's platform is well-suited to address the underlying connectivity and identity challenges that AI deployments expose.

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Network World

Network World reports on Tailscale's $160 million Series C funding round, detailing the company's WireGuard-based VPN technology, its open-source strategy, and how surging demand from AI companies such as Perplexity, Mistral, Cohere, Groq, and Hugging Face has driven rapid growth.

Companies:Tailscale

BNN Bloomberg

Tailscale Inc., a security startup based in Toronto, has raised US$160 million from investors — a significant haul for the Canadian company. The deal values the startup at about $1.5 billion.

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Stratechery

Ben Thompson of Stratechery interviews Tailscale co-founder and CEO Avery Pennarun, covering the company's origin story, its peer-to-peer VPN architecture built on WireGuard, and why its disruptive approach has attracted over 10,000 business customers and 500,000 weekly active users.

Companies:Tailscale