1023: Mosh, Caddy & Tailscale: A Remote Dev Deep Dive

Scott Tolinsky and Wes Bos have been running their development process on a remote machine instead of their laptops, and they are never going back. The trigger was a familiar pain: "Let me tell you the amount of times I've had to reboot my computer in the last like six months. Unbelievable." Wes was hitting it too — endless apps running in the background, child processes from AI agents going rogue, and the dread of losing 18 terminal tabs on a restart. The solution is a stack of free or cheap tools (Mosh, Caddy, Tailscale, Herder, Zed) that lets you close your laptop, keep processes running, and access everything from any device — phone, iPad, or a different computer entirely.

Why Remote Development Works

The core mechanism is detachment. When you run your dev process on a machine that is not your laptop, you can close the laptop without killing anything. That means better battery life (you are not running 8,000 things locally), the ability to access processes from any machine, and the freedom to walk away while an agent works. Scott demonstrated the trust level: he loaded his slides for a talk in Amsterdam from his Mac Mini back in Denver, in front of a thousand people. "It all worked," he said. "So that means it was a valid approach."