diff --git a/src/agents/pi-embedded-helpers/errors.ts b/src/agents/pi-embedded-helpers/errors.ts
index 8f6dbe652bb..fac44b8888c 100644
--- a/src/agents/pi-embedded-helpers/errors.ts
+++ b/src/agents/pi-embedded-helpers/errors.ts
@@ -208,7 +208,7 @@ const HTTP_ERROR_HINTS = [
   "permission",
 ];
 
-type Http402Reason = "billing" | "rate_limit";
+type PaymentRequiredFailoverReason = Extract<FailoverReason, "billing" | "rate_limit">;
 
 const BILLING_402_HINTS = [
   "insufficient credits",
@@ -220,56 +220,54 @@ const BILLING_402_HINTS = [
   "top up",
 ] as const;
 
+const PERIODIC_402_HINTS = ["daily", "weekly", "monthly"] as const;
 const RETRYABLE_402_RETRY_HINTS = ["try again", "retry", "temporary", "cooldown"] as const;
 const RETRYABLE_402_LIMIT_HINTS = ["usage limit", "rate limit", "organization usage"] as const;
-const BILLING_402_HARD_CAP_RE =
-  /\b(?:billing hard limit|hard limit reached|maximum allowed(?:\s+(?:daily|weekly|monthly))?(?:\s+spend(?:ing)?)?\s+limit)\b/i;
+const RETRYABLE_402_SCOPED_HINTS = ["organization", "workspace"] as const;
+const RETRYABLE_402_SCOPED_RESULT_HINTS = [
+  "billing period",
+  "exceeded",
+  "reached",
+  "exhausted",
+] as const;
 const RAW_402_MARKER_RE =
   /["']?(?:status|code)["']?\s*[:=]\s*402\b|\bhttp\s*402\b|\berror(?:\s+code)?\s*[:=]?\s*402\b|\b(?:got|returned|received)\s+(?:a\s+)?402\b|^\s*402\s+payment required\b/i;
 const LEADING_402_WRAPPER_RE =
   /^(?:error[:\s-]+)?(?:(?:http\s*)?402(?:\s+payment required)?|payment required)(?:[:\s-]+|$)/i;
-const RETRYABLE_402_PERIODIC_USAGE_OR_SPEND_RE =
-  /\b(?:daily|weekly|monthly)(?:\/(?:daily|weekly|monthly))*\s+(?:usage|spend(?:ing)?)\s+limit(?:s)?(?:\s+(?:exhausted|reached|exceeded))?\b/i;
-const RETRYABLE_402_SCOPED_SPEND_LIMIT_RE =
-  /\b(?:organization|workspace)\s+(?:spend(?:ing)?\s+)?limit(?:s)?(?:\s+(?:reached|exhausted|exceeded))?\b/i;
-const RETRYABLE_402_SCOPED_LIMIT_EXCEEDED_RE =
-  /\b(?:organization|workspace)\b[\s\S]{0,30}\blimit(?:s)?\b[\s\S]{0,30}\bexceeded\b/i;
-const RETRYABLE_402_SCOPED_BILLING_PERIOD_RE =
-  /\b(?:organization|workspace)\b[\s\S]{0,30}\blimit(?:s)?\b[\s\S]{0,30}\bbilling period\b/i;
 
 function includesAnyHint(text: string, hints: readonly string[]): boolean {
-  const lower = text.toLowerCase();
-  return hints.some((hint) => lower.includes(hint));
+  return hints.some((hint) => text.includes(hint));
 }
 
 function hasExplicit402BillingSignal(text: string): boolean {
-  return includesAnyHint(text, BILLING_402_HINTS) || BILLING_402_HARD_CAP_RE.test(text);
+  return (
+    includesAnyHint(text, BILLING_402_HINTS) ||
+    text.includes("billing hard limit") ||
+    text.includes("hard limit reached") ||
+    (text.includes("maximum allowed") && text.includes("limit"))
+  );
 }
 
 function hasRetryable402TransientSignal(text: string): boolean {
-  const lower = text.toLowerCase();
+  const hasPeriodicHint = includesAnyHint(text, PERIODIC_402_HINTS);
+  const hasSpendLimit = text.includes("spend limit") || text.includes("spending limit");
+  const hasScopedHint = includesAnyHint(text, RETRYABLE_402_SCOPED_HINTS);
   return (
     (includesAnyHint(text, RETRYABLE_402_RETRY_HINTS) &&
       includesAnyHint(text, RETRYABLE_402_LIMIT_HINTS)) ||
-    RETRYABLE_402_PERIODIC_USAGE_OR_SPEND_RE.test(text) ||
-    (includesAnyHint(lower, ["daily", "weekly", "monthly"]) &&
-      lower.includes("limit") &&
-      lower.includes("reset")) ||
-    RETRYABLE_402_SCOPED_SPEND_LIMIT_RE.test(text) ||
-    RETRYABLE_402_SCOPED_LIMIT_EXCEEDED_RE.test(text) ||
-    RETRYABLE_402_SCOPED_BILLING_PERIOD_RE.test(text)
+    (hasPeriodicHint && (text.includes("usage limit") || hasSpendLimit)) ||
+    (hasPeriodicHint && text.includes("limit") && text.includes("reset")) ||
+    (hasScopedHint &&
+      text.includes("limit") &&
+      (hasSpendLimit || includesAnyHint(text, RETRYABLE_402_SCOPED_RESULT_HINTS)))
   );
 }
 
 function normalize402Message(raw: string): string {
-  let normalized = raw.trim();
-  while (LEADING_402_WRAPPER_RE.test(normalized)) {
-    normalized = normalized.replace(LEADING_402_WRAPPER_RE, "").trim();
-  }
-  return normalized;
+  return raw.trim().toLowerCase().replace(LEADING_402_WRAPPER_RE, "").trim();
 }
 
-function classify402Message(message: string): Http402Reason {
+function classify402Message(message: string): PaymentRequiredFailoverReason {
   const normalized = normalize402Message(message);
   if (!normalized) {
     return "billing";
@@ -286,7 +284,7 @@ function classify402Message(message: string): Http402Reason {
   return "billing";
 }
 
-function classifyFailoverReasonFromRaw402Message(raw: string): Http402Reason | null {
+function classifyFailoverReasonFrom402Text(raw: string): PaymentRequiredFailoverReason | null {
   if (!RAW_402_MARKER_RE.test(raw)) {
     return null;
   }
@@ -925,9 +923,9 @@ export function classifyFailoverReason(raw: string): FailoverReason | null {
   if (isModelNotFoundErrorMessage(raw)) {
     return "model_not_found";
   }
-  const raw402Reason = classifyFailoverReasonFromRaw402Message(raw);
-  if (raw402Reason) {
-    return raw402Reason;
+  const reasonFrom402Text = classifyFailoverReasonFrom402Text(raw);
+  if (reasonFrom402Text) {
+    return reasonFrom402Text;
   }
   if (isPeriodicUsageLimitErrorMessage(raw)) {
     return isBillingErrorMessage(raw) ? "billing" : "rate_limit";