May 2022 Summaries

Tailscale's May 2022 newsletter highlights a range of developments and community activities, showcasing the company's commitment to growth and innovation. The release of Tailscale v1.26 introduces features like MagicDNS support for DNS/TCP and improved UI options, while also marking the launch of a standalone macOS app. The company achieved SOC 2 Type I compliance, emphasizing their dedication to security, and updated their documentation for better user navigation. Tailscale expanded its capabilities with a new Docker Desktop extension, enabling easier sharing of container ports. The company also engaged in various events, including Gitpod’s DevX conference and DockerCon, and continues to seek motivated individuals for remote roles. The newsletter encourages community feedback and contributions, while also referencing discussions on using Tailscale across different platforms and contexts, such as gaming and development.

Tailscale, a company focused on security and privacy, has achieved SOC 2 Type I compliance, underscoring its commitment to safeguarding user data. This certification verifies Tailscale's internal procedures and policies, as assessed by an independent auditor, and highlights the company's robust security controls such as end-to-end encryption with WireGuard, regular data backups, and rigorous access management using SSO and MFA. Tailscale collaborates with the security consulting firm Latacora for comprehensive security program management and requires employees to undergo regular security training. Despite achieving SOC 2 Type I compliance, Tailscale continues to enhance its security measures and is working towards obtaining SOC 2 Type II compliance. The company emphasizes transparency in its operations, aiming to build trust with users by openly sharing its security practices and the rationale behind its decisions.

In a detailed conversation, Tailscale's Avery Pennarun and Dave Anderson discuss their partnership with security firm Latacora, highlighting their journey towards SOC 2 compliance and the broader challenges of maintaining a robust security posture. The discourse delves into Tailscale's proactive approach to security, which includes acknowledging their blind spots and striving for the highest security standards to avoid being the weakest link in their customers' security chains. Latacora, co-founded by Laurens Van Houtven, offers insights into their unique business model that caters specifically to startups, emphasizing the need for a dedicated security program rather than just external audits. Through anecdotes, they illustrate common pitfalls in startup security, such as underestimating long-term security needs and the importance of internalizing security practices. The dialogue also explores Tailscale's philosophy on security architecture reviews, the necessity of expert networks for complex security issues, and the evolving nature of their engagement with Latacora, which has transitioned from short-term to long-term support. The conversation concludes with reflections on the role of SOC 2 compliance in improving security practices, underscoring the importance of treating it as an opportunity for genuine enhancement rather than a mere checkbox exercise.

Tailscale has launched an extension for Docker Desktop, announced at DockerCon, which enhances the development experience by securely connecting to necessary resources like internal tools and databases from any location. This extension simplifies the process of sharing exposed container ports from a local machine with other users and devices on a tailnet, allowing for seamless collaboration on code reviews and feedback sharing. By integrating with single sign-on (SSO) from identity providers, Tailscale facilitates safe resource sharing within organizations through access controls. The extension operates in userspace networking mode, enabling Tailscale to function without creating a VPN tunnel device, which is particularly useful in container environments. By using the Tailscale extension, developers can provide their containers with a static IP for communication, even across container layers, and can manage access to these containers through the tailnet. To utilize the extension effectively, users must run Tailscale on both the host device and Docker Desktop, and enable MagicDNS for easy access to containers via human-readable DNS names.

Tailscale, a company founded in 2019 by David Carney, David Crawshaw, and Avery Pennarun, has secured $100 million in Series B financing to further its mission of simplifying small-scale software development and enhancing the Internet's functionality. The company focuses on making internal software tools easy to use by addressing the non-scalable aspects of projects that don't need public exposure, such as internal dashboards and HR databases. Tailscale's product, often described as "magic" by users, is lauded for its high quality and ease of use, fostering growth through word-of-mouth recommendations. Despite industry skepticism regarding the balance between ease of use and security, Tailscale has gained traction by offering a VPN solution that exceeds typical reliability standards. As the company grows, it plans to use the funding to maintain its commitment to quality, community, and sustainable growth rather than prioritizing aggressive revenue expansion, aiming to "fix the Internet" by returning to a simpler, more secure digital experience akin to the early days of computing.