diff --git a/src/resources/extensions/sf/workflow-helpers.js b/src/resources/extensions/sf/workflow-helpers.js
index e3acc68fd..ead7d4bb0 100644
--- a/src/resources/extensions/sf/workflow-helpers.js
+++ b/src/resources/extensions/sf/workflow-helpers.js
@@ -69,12 +69,16 @@ export async function checkNeedsReassessment(base, mid, _state, _prefs) {
 				const hasIncomplete = slices.some((s) => s.status !== "complete");
 				if (completedSliceIds.length === 0 || !hasIncomplete) return null;
 				const lastCompleted = completedSliceIds[completedSliceIds.length - 1];
-				const assessmentFile = resolveSliceFile(
-					base,
-					mid,
-					lastCompleted,
-					"ASSESS",
-				);
+				// Try both "ASSESSMENT" (canonical, e.g. S03-ASSESSMENT.md) and
+				// the legacy "ASSESS" suffix. Without the ASSESSMENT branch the
+				// dispatcher re-dispatched reassess-roadmap indefinitely because
+				// resolveFile's pattern (`${idPrefix}-.*-${suffix}.md`) requires
+				// at least one char before `-ASSESS`, so `S03-ASSESSMENT.md`
+				// never matched suffix "ASSESS". Witnessed 2026-05-17 on
+				// M010/S03 — 70+ degenerate iterations.
+				const assessmentFile =
+					resolveSliceFile(base, mid, lastCompleted, "ASSESSMENT") ??
+					resolveSliceFile(base, mid, lastCompleted, "ASSESS");
 				if (assessmentFile && existsSync(assessmentFile)) return null;
 				return { sliceId: lastCompleted };
 			}