diff --git a/.github/scripts/issue-quality-core.cjs b/.github/scripts/issue-quality-core.cjs
index c6abfacf1d..40fadaca6d 100644
--- a/.github/scripts/issue-quality-core.cjs
+++ b/.github/scripts/issue-quality-core.cjs
@@ -1134,10 +1134,8 @@ const REPRO_PATH_RE = new RegExp([
     "~?/[\\w.@-]+(?:/[\\w.@-]+)+",
     "[A-Za-z]:\\\\(?:[\\w.@-]+\\\\)+[\\w.@-]+",
     "~?/[\\w.@-]+/[\\w.@-]+\\.(?:json|yaml|yml|toml|conf|log|env|txt|ts|js|tsx|jsx|sh|ps1|py)",
-    "[\\w.@-]+\\.(?:json|yaml|yml|toml|conf|log|env)\\b",
-].join("|"));
-const ACTIONABLE_REPRO_RE = new RegExp(
-  [REPRO_COMMAND_RE.source, REPRO_FAILURE_RE.source, REPRO_PATH_RE.source].join("|"),
+    "(?:^|[^\\w.@-])[\\w.@-]+\\.(?:json|yaml|yml|toml|conf|log|env)\\b",
+].join("|"),
   "i",
 );
 
@@ -1151,9 +1149,18 @@ const EMPTY_FENCE_RE = /^[ \t]{0,3}(?:```+|~~~+)\s*\n\s*\n[ \t]{0,3}(?:```+|~~~+
  * count as actionable when their body contains non-whitespace content.
  */
 function hasActionableReproductionDetail(text) {
+  if (typeof text !== "string") return false;
+  // Avoid Markdown cleanup and path matching when the raw input cannot contain
+  // actionable syntax. Fences remain eligible through their ` / ~ sigils.
+  if (!/[./\\`~]/.test(text) && !REPRO_COMMAND_RE.test(text) && !REPRO_FAILURE_RE.test(text)) {
+    return false;
+  }
   const c = clean(text);
   if (!c) return false;
-  if (ACTIONABLE_REPRO_RE.test(c)) return true;
+  if (REPRO_COMMAND_RE.test(c) || REPRO_FAILURE_RE.test(c)) return true;
+  // A boundary-anchored filename avoids retrying the same long token from each
+  // successive character while preserving case-insensitive extension matches.
+  if (/[./\\]/.test(c) && REPRO_PATH_RE.test(c)) return true;
   // Fenced blocks: only count when the body has non-whitespace content.
   if (/```|~~~/.test(c)) {
     const parts = stripFencedActionableContent(c);
diff --git a/.github/scripts/issue-quality.test.cjs b/.github/scripts/issue-quality.test.cjs
index bae797ec41..15a4ec68ab 100644
--- a/.github/scripts/issue-quality.test.cjs
+++ b/.github/scripts/issue-quality.test.cjs
@@ -713,6 +713,13 @@ describe("validateIssue - feature", () => {
     assert.equal(hasActionableReproductionDetail("```\nSIGSEGV at 0x0000\n```"), true);
   });
 
+  it("bounds long non-matching reproduction path tokens", () => {
+    const startedAt = performance.now();
+    assert.equal(hasActionableReproductionDetail(`${"a".repeat(60_000)}.unknown`), false);
+    assert.ok(performance.now() - startedAt < 500, "actionable reproduction check took too long");
+    assert.equal(hasActionableReproductionDetail("CONFIG.JSON"), true);
+  });
+
   it("rejects fenced placeholder-only examples", () => {
     const fencedPlaceholders = [
       "```\nN/A\n```",