Headroom proxy auto-start via Windows Task Scheduler at login

Headroom launches at logon via Task Scheduler. Runs as logged-in user with env + creds

Headroom autostart via Task Scheduler at login

Decision

Headroom proxy is launched by a Windows Task Scheduler task triggered on user logon. Not a Windows Service (no SYSTEM-account env-var hassles, no LSA-secrets path). Not a Startup folder shortcut (no failure handling, no restart-on-crash).

Why

User locked this on 2026-06-26 (Q11). Task Scheduler gets the user’s HKCU env vars, has built-in restart-on-failure, and survives Windows updates better than service installs.

How to apply

• Task name: Headroom Proxy (oriz).
• Trigger: “At log on of ”.
• Action: wt.exe (or hidden cmd) invoking the Headroom binary with --persistent flag.
• Settings: “If the task fails, restart every 1 minute” — up to 3 restarts.
• Run only when logged on (no need for SYSTEM execution).
• Install script lives in the Headroom repo’s scripts/install-windows.ps1.

Captured

2026-06-26 session, Q11 of 24-question grill.

Related

• headroom-always-on-proxy-2026-06-26
• headroom-install-all-paths-2026-06-26

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