May 2021 Summaries

Tailscale's May 2021 update highlights significant developments, including the release of Tailscale v1.8 and the introduction of Taildrop, a feature enabling seamless file transfers between personal devices. The newsletter showcases community contributions such as a Statusbar UI for Ubuntu and various integrations with FreeNAS, Raspberry Pi, and AWS using Terraform. Taildrop, in alpha, facilitates encrypted peer-to-peer file transfers without relying on third-party servers, although currently limited to personal devices only. The update also unveils improvements like Split DNS, enhancing DNS configuration flexibility, and new admin console features for toggling experimental functionalities. The company encourages feedback to enhance its offerings and maintains a focus on user-driven development.

Taildrop is a Tailscale feature that facilitates secure, peer-to-peer file transfers between personal devices without relying on cloud services, thus avoiding internet-based security vulnerabilities. Currently in public alpha and requiring Tailscale v1.8 or later, Taildrop allows users to send various files, from sensitive documents to family photos and screenshots, across different platforms while ensuring encryption during the transfer process. Unlike Apple's Airdrop, which is limited to nearby Apple devices, Taildrop enables file sharing regardless of device location. The feature is particularly useful for transferring files like Google Photos albums to personal servers, especially given the recent changes in Google Photos' storage policies.

Tailscale, a software that facilitates secure networking, enables users to connect devices seamlessly without the need for traditional VPN setups. The process begins when a user shares a service, such as a prototype sloth webcam, using Tailscale, which relies on a TUN/TAP network interface to route packets. Unlike privacy VPNs that route all network traffic through a cloud server, Tailscale routes only specific IP addresses within its network, enhancing privacy by ensuring that Tailscale-owned servers never see unencrypted traffic. Built on WireGuard, Tailscale encrypts data at the IP layer, ensuring secure transmission without needing HTTPS. The encryption process starts once the packet arrives at the Tailscale process and involves a handshake to establish a shared key for encryption. Tailscale's NAT traversal finds a direct path for communication, and once a handshake is complete, the packet is encrypted and sent over the internet to the recipient's device. Upon arrival, the packet is decrypted, checked against Tailscale's access controls, and finally delivered to the intended application, allowing users to access shared services securely and efficiently.

The blog post by Naman Sood discusses a method for automating the deployment of a personal blog using GitHub Actions and Tailscale, focusing on security and efficiency. Sood describes the challenges of deploying updates to a web server written in Go, highlighting how changes require manual compilation and restarting. To automate this process, Sood developed a GitHub Action that builds and packages the application, then deploys it via Tailscale, a VPN service that secures server access. One issue encountered was the need for the GitHub Action to join the Tailscale network, which was initially complicated by the persistent registration of Docker containers. This was resolved by using ephemeral authentication keys, which allow temporary access without permanent registration. Sood, an intern at Tailscale, also contributed to creating a GitHub Action for Tailscale connections, facilitating seamless integration with CI/CD workflows. The solution not only enhances deployment efficiency but also broadens the potential for using Tailscale in various cloud environments.

Tailscale v1.8 introduces a range of enhancements and new features, focusing on general improvements, DNS configuration, and file-sharing capabilities. This update includes the long-awaited "tailscale logout" command, improved client access to exit node public IPs, and a "tailscale bugreport" subcommand to facilitate log marking for support troubleshooting. Significant efforts have been made to address DNS configuration issues and introduce a beta feature called Split DNS, which allows users to set DNS servers for specific domain names, complementing the existing MagicDNS. The admin console now features a General settings page for easier feature toggling and previews. Additionally, the alpha feature Taildrop enables secure file sending between Tailscale-connected devices, requiring both devices to be updated to version 1.8. Users are encouraged to provide feedback via email or Twitter to help improve future versions.