Diagnoses and fixes conflicts between Tailscale and proxy/VPN tools (Shadowrocket, Clash, Surge) on macOS. Covers five conflict layers - (1) route hijacking, (2) HTTP proxy env var interception, (3) system proxy bypass, (4) SSH ProxyCommand double tunneling, and (5) VM/container runtime proxy propagation (OrbStack/Docker). Includes SOP for remote development via SSH tunnels with proxy-safe Makefile patterns. Use when Tailscale ping works but SSH/HTTP times out, when browser returns 503 but curl works, when git push fails with "failed to begin relaying via HTTP", when Docker pull times out behind TUN/VPN, when setting up Tailscale SSH to WSL instances, or when bootstrapping remote dev environments over Tailscale.