diff --git a/src/resources/extensions/sf/auto/loop.js b/src/resources/extensions/sf/auto/loop.js
index 326175431..7279589bd 100644
--- a/src/resources/extensions/sf/auto/loop.js
+++ b/src/resources/extensions/sf/auto/loop.js
@@ -1136,31 +1136,74 @@ export async function autoLoop(ctx, pi, s, deps) {
 							const midTitle = sfState.activeMilestone?.title ?? "";
 							const sliceId = sfState.activeSlice?.id ?? "reassess";
 							if (mid) {
-								ctx.ui.notify(
-									`Health issues detected with slice references — queuing reassess-roadmap instead of pausing.`,
-									"warning",
-									{
-										noticeKind: NOTICE_KIND.SYSTEM_NOTICE,
-										dedupe_key: "doctor-health-reassess-roadmap",
-									},
-								);
-								const { buildReassessRoadmapPrompt } = await import(
-									"../auto-prompts.js"
-								);
-								const reassessPrompt = await buildReassessRoadmapPrompt(
-									mid,
-									midTitle,
-									sliceId,
-									s.basePath,
-								);
-								s.sidecarQueue.unshift({
-									kind: "hook",
-									unitType: "reassess-roadmap",
-									unitId: `${mid}/${sliceId}`,
-									prompt: `## Doctor Health Issues\n\n${healthCheck.issues.map((i) => `- ${i}`).join("\n")}\n\n${reassessPrompt}`,
-								});
-								finishTurn("retry");
-								continue;
+								// Convergence guard (Ralph Wiggum): if the SAME
+								// reassess-roadmap target just ran 3+ consecutive
+								// times the doctor's slice-ref issues evidently
+								// aren't being resolved by reassessment. Skip
+								// the redispatch, file self-feedback, and fall
+								// through to normal pre-dispatch so the existing
+								// detectStuck path (Rule 2) can break the loop
+								// instead of looping forever burning tokens.
+								const newKey = `reassess-roadmap:${mid}/${sliceId}`;
+								const recentKeys = (loopState.recentUnits || [])
+									.slice(-3)
+									.map((u) => u?.key);
+								const stuckOnReassess =
+									recentKeys.length === 3 &&
+									recentKeys.every((k) => k === newKey);
+								if (stuckOnReassess) {
+									ctx.ui.notify(
+										`Convergence guard: ${newKey} succeeded 3 consecutive times but doctor's slice-ref issues persist. Skipping redispatch — running normal pre-dispatch so detectStuck can break the loop.`,
+										"warning",
+										{
+											noticeKind: NOTICE_KIND.SYSTEM_NOTICE,
+											dedupe_key: "convergence-guard-reassess",
+										},
+									);
+									try {
+										recordSelfFeedback(
+											{
+												kind: "engine-loop:non-converging-redispatch",
+												severity: "high",
+												summary: `${newKey} dispatched 3 consecutive times with success exit, but doctor's slice-reference health issues persist. Convergence guard skipped further redispatch.`,
+												evidence: `Doctor health issues persisting after 3 successful reassess-roadmap cycles: ${healthCheck.issues.slice(0, 5).join(" | ")}`,
+											},
+											s.basePath,
+										);
+									} catch {
+										// Filing must never block the loop's recovery path.
+									}
+									// Fall through to normal pre-dispatch (no
+									// unshift, no finishTurn — the next phases
+									// will either advance state via a different
+									// unit or hit detectStuck and bail.
+								} else {
+									ctx.ui.notify(
+										`Health issues detected with slice references — queuing reassess-roadmap instead of pausing.`,
+										"warning",
+										{
+											noticeKind: NOTICE_KIND.SYSTEM_NOTICE,
+											dedupe_key: "doctor-health-reassess-roadmap",
+										},
+									);
+									const { buildReassessRoadmapPrompt } = await import(
+										"../auto-prompts.js"
+									);
+									const reassessPrompt = await buildReassessRoadmapPrompt(
+										mid,
+										midTitle,
+										sliceId,
+										s.basePath,
+									);
+									s.sidecarQueue.unshift({
+										kind: "hook",
+										unitType: "reassess-roadmap",
+										unitId: `${mid}/${sliceId}`,
+										prompt: `## Doctor Health Issues\n\n${healthCheck.issues.map((i) => `- ${i}`).join("\n")}\n\n${reassessPrompt}`,
+									});
+									finishTurn("retry");
+									continue;
+								}
 							}
 						}
 					}