SSH MCP and Tailscale: Docker Migration Guide

Daniel built an SSH MCP server that uses Tailscale to connect his agent to remote VPS boxes. The setup works beautifully — until Docker containers need to reach services on other tailnet nodes. This episode walks through the three failure patterns that emerge when you try to migrate from public IPs to tailnet addresses: split DNS, name collisions, and the localhost bind problem. We cover the sidecar pattern for giving containers tailnet access, the real scope of work when migrating compose files, and the tradeoffs of depending on Tailscale's control plane. Episode #197624 — open it directly at myweirdprompts.com/197624