June 2022 Summaries

In June 2022, Tailscale announced the beta release of Tailscale SSH, a feature designed to simplify SSH connections by bypassing the need for traditional SSH key management and offering direct authentication through Tailscale's identity system. This innovation allows users to enable SSH connections with a single command, eliminating the need for configuration changes, jump boxes, proxies, and avoiding port conflicts. The newsletter highlights community contributions, including Pat Reagan's documentation of his experience and Kris Nova's Twitch tutorial on Tailscale usage. Additionally, discussions from Tailscale engineers Brad Fitzpatrick and Maisem Ali provide insights into the development of Tailscale SSH. Tailscale is also featured in various integrations and use cases such as connecting a Windows 11 machine to an iPad, creating a dynamic Ansible inventory, and enhancing container networking security. The newsletter encourages feedback from users and highlights the broader applications of Tailscale in personal and cloud infrastructure projects.

Tailscale SSH is a new feature designed to simplify and secure SSH connections within a Tailscale network by using Tailscale identities instead of traditional SSH keys. This approach eliminates the need for managing SSH keys, as it leverages WireGuard for authentication and encryption, and allows for connections between devices based on access control lists (ACLs). Tailscale SSH can reroute incoming traffic to an SSH service within the Tailscale daemon, bypassing the traditional SSH server, and can integrate with existing identity providers for clear user-device associations. For high-risk connections, a check mode is available requiring recent re-authentication, enhancing security. Tailscale SSH is available on Linux devices and can be used concurrently with existing SSH configurations, allowing for a gradual rollout. It also supports the use of SSH access rules to define user permissions and connection authorizations. Tailscale SSH aims to eliminate the complexity of managing SSH keys, setting up bastion hosts, and reducing exposure to the open internet, and it is currently in beta, included in all Tailscale plans.

Tailscale, a VPN service, now offers a standalone macOS application starting with version 1.26, enabling easier deployment in work environments where not everyone may have an Apple ID, particularly through mobile device management (MDM) solutions. This standalone version maintains the same functionality as the App Store version and is compatible with macOS's two primary methods for managing VPNs: the Network Extension and generic system extensions. While Network Extension is typically used for sandbox applications via the App Store, generic system extensions are employed for applications outside the App Store. Tailscale effectively supports both methods, allowing flexibility in how it operates on macOS devices.