diff --git a/src/headless.ts b/src/headless.ts
index dc924b79a..134a0215a 100644
--- a/src/headless.ts
+++ b/src/headless.ts
@@ -634,6 +634,41 @@ async function runHeadlessOnce(
 			options.command = "new-milestone";
 			options.chainAutonomous = true;
 			options.contextText = buildAutoBootstrapContext(process.cwd());
+		} else if (!options.commandArgs.includes("--skip-triage")) {
+			// Auto-drain the self-feedback triage queue before entering the
+			// autonomous dispatch loop. Without this, items in
+			// .sf/self-feedback.jsonl sit unprocessed and SF can only work on
+			// the active milestone — defeating the self-heal thesis.
+			// Comment on headless-triage at line 917-921 acknowledges that
+			// autonomous-loop followUp delivery was unreliable (sf-mp4rxkwb-l4baga),
+			// hence the deterministic operator path. This wires the deterministic
+			// path BEFORE the dispatch loop so autonomous == triage-then-dispatch.
+			// Skipped when resuming (resumeSession check above) or when the user
+			// passes --skip-triage to opt out (e.g. to debug a specific milestone
+			// without backlog churn).
+			try {
+				const { handleTriage } = await import("./headless-triage.js");
+				if (!options.json) {
+					process.stderr.write(
+						"[headless] autonomous: draining self-feedback triage queue first...\n",
+					);
+				}
+				await handleTriage(process.cwd(), {
+					apply: true,
+					json: !!options.json,
+					max: 5, // bound the up-front cost; remainder flushes on next session_start
+				});
+			} catch (err) {
+				// Triage failure must not block autonomous mode — the loop's own
+				// dispatch will keep going; backlog will just stay until next run.
+				if (!options.json) {
+					process.stderr.write(
+						`[headless] autonomous: triage drain failed (non-fatal): ${
+							err instanceof Error ? err.message : String(err)
+						}\n`,
+					);
+				}
+			}
 		}
 	}
 	const isNewMilestone = options.command === "new-milestone";