diff --git a/src/security/safe-regex.test.ts b/src/security/safe-regex.test.ts
index 30fa27936..fe6f10427 100644
--- a/src/security/safe-regex.test.ts
+++ b/src/security/safe-regex.test.ts
@@ -4,11 +4,15 @@ import { compileSafeRegex, hasNestedRepetition } from "./safe-regex.js";
 describe("safe regex", () => {
   it("flags nested repetition patterns", () => {
     expect(hasNestedRepetition("(a+)+$")).toBe(true);
+    expect(hasNestedRepetition("(a|aa)+$")).toBe(true);
     expect(hasNestedRepetition("^(?:foo|bar)$")).toBe(false);
+    expect(hasNestedRepetition("^(ab|cd)+$")).toBe(false);
   });
 
   it("rejects unsafe nested repetition during compile", () => {
     expect(compileSafeRegex("(a+)+$")).toBeNull();
+    expect(compileSafeRegex("(a|aa)+$")).toBeNull();
+    expect(compileSafeRegex("(a|aa){2}$")).toBeInstanceOf(RegExp);
   });
 
   it("compiles common safe filter regex", () => {
diff --git a/src/security/safe-regex.ts b/src/security/safe-regex.ts
index 4f4f6921a..04c9be61a 100644
--- a/src/security/safe-regex.ts
+++ b/src/security/safe-regex.ts
@@ -1,22 +1,68 @@
 type QuantifierRead = {
   consumed: number;
+  minRepeat: number;
+  maxRepeat: number | null;
 };
 
 type TokenState = {
   containsRepetition: boolean;
+  hasAmbiguousAlternation: boolean;
+  minLength: number;
+  maxLength: number;
 };
 
 type ParseFrame = {
   lastToken: TokenState | null;
   containsRepetition: boolean;
+  hasAlternation: boolean;
+  branchMinLength: number;
+  branchMaxLength: number;
+  altMinLength: number | null;
+  altMaxLength: number | null;
 };
 
 const SAFE_REGEX_CACHE_MAX = 256;
 const safeRegexCache = new Map<string, RegExp | null>();
 
+function createParseFrame(): ParseFrame {
+  return {
+    lastToken: null,
+    containsRepetition: false,
+    hasAlternation: false,
+    branchMinLength: 0,
+    branchMaxLength: 0,
+    altMinLength: null,
+    altMaxLength: null,
+  };
+}
+
+function addLength(left: number, right: number): number {
+  if (!Number.isFinite(left) || !Number.isFinite(right)) {
+    return Number.POSITIVE_INFINITY;
+  }
+  return left + right;
+}
+
+function multiplyLength(length: number, factor: number): number {
+  if (!Number.isFinite(length)) {
+    return factor === 0 ? 0 : Number.POSITIVE_INFINITY;
+  }
+  return length * factor;
+}
+
+function recordAlternative(frame: ParseFrame): void {
+  if (frame.altMinLength === null || frame.altMaxLength === null) {
+    frame.altMinLength = frame.branchMinLength;
+    frame.altMaxLength = frame.branchMaxLength;
+    return;
+  }
+  frame.altMinLength = Math.min(frame.altMinLength, frame.branchMinLength);
+  frame.altMaxLength = Math.max(frame.altMaxLength, frame.branchMaxLength);
+}
+
 export function hasNestedRepetition(source: string): boolean {
   // Conservative parser: reject patterns where a repeated token/group is repeated again.
-  const frames: ParseFrame[] = [{ lastToken: null, containsRepetition: false }];
+  const frames: ParseFrame[] = [createParseFrame()];
   let inCharClass = false;
 
   const emitToken = (token: TokenState) => {
@@ -25,6 +71,17 @@ export function hasNestedRepetition(source: string): boolean {
     if (token.containsRepetition) {
       frame.containsRepetition = true;
     }
+    frame.branchMinLength = addLength(frame.branchMinLength, token.minLength);
+    frame.branchMaxLength = addLength(frame.branchMaxLength, token.maxLength);
+  };
+
+  const emitSimpleToken = () => {
+    emitToken({
+      containsRepetition: false,
+      hasAmbiguousAlternation: false,
+      minLength: 1,
+      maxLength: 1,
+    });
   };
 
   for (let i = 0; i < source.length; i += 1) {
@@ -32,7 +89,7 @@ export function hasNestedRepetition(source: string): boolean {
 
     if (ch === "\\") {
       i += 1;
-      emitToken({ containsRepetition: false });
+      emitSimpleToken();
       continue;
     }
 
@@ -45,25 +102,47 @@ export function hasNestedRepetition(source: string): boolean {
 
     if (ch === "[") {
       inCharClass = true;
-      emitToken({ containsRepetition: false });
+      emitSimpleToken();
       continue;
     }
 
     if (ch === "(") {
-      frames.push({ lastToken: null, containsRepetition: false });
+      frames.push(createParseFrame());
       continue;
     }
 
     if (ch === ")") {
       if (frames.length > 1) {
         const frame = frames.pop() as ParseFrame;
-        emitToken({ containsRepetition: frame.containsRepetition });
+        if (frame.hasAlternation) {
+          recordAlternative(frame);
+        }
+        const groupMinLength = frame.hasAlternation
+          ? (frame.altMinLength ?? 0)
+          : frame.branchMinLength;
+        const groupMaxLength = frame.hasAlternation
+          ? (frame.altMaxLength ?? 0)
+          : frame.branchMaxLength;
+        emitToken({
+          containsRepetition: frame.containsRepetition,
+          hasAmbiguousAlternation:
+            frame.hasAlternation &&
+            frame.altMinLength !== null &&
+            frame.altMaxLength !== null &&
+            frame.altMinLength !== frame.altMaxLength,
+          minLength: groupMinLength,
+          maxLength: groupMaxLength,
+        });
       }
       continue;
     }
 
     if (ch === "|") {
       const frame = frames[frames.length - 1];
+      frame.hasAlternation = true;
+      recordAlternative(frame);
+      frame.branchMinLength = 0;
+      frame.branchMaxLength = 0;
       frame.lastToken = null;
       continue;
     }
@@ -78,13 +157,32 @@ export function hasNestedRepetition(source: string): boolean {
       if (token.containsRepetition) {
         return true;
       }
+      if (token.hasAmbiguousAlternation && quantifier.maxRepeat === null) {
+        return true;
+      }
+
+      const previousMinLength = token.minLength;
+      const previousMaxLength = token.maxLength;
+      token.minLength = multiplyLength(token.minLength, quantifier.minRepeat);
+      token.maxLength =
+        quantifier.maxRepeat === null
+          ? Number.POSITIVE_INFINITY
+          : multiplyLength(token.maxLength, quantifier.maxRepeat);
       token.containsRepetition = true;
       frame.containsRepetition = true;
+      frame.branchMinLength = frame.branchMinLength - previousMinLength + token.minLength;
+
+      const branchMaxBase =
+        Number.isFinite(frame.branchMaxLength) && Number.isFinite(previousMaxLength)
+          ? frame.branchMaxLength - previousMaxLength
+          : Number.POSITIVE_INFINITY;
+      frame.branchMaxLength = addLength(branchMaxBase, token.maxLength);
+
       i += quantifier.consumed - 1;
       continue;
     }
 
-    emitToken({ containsRepetition: false });
+    emitSimpleToken();
   }
 
   return false;
@@ -92,12 +190,20 @@ export function hasNestedRepetition(source: string): boolean {
 
 function readQuantifier(source: string, index: number): QuantifierRead | null {
   const ch = source[index];
-  if (ch === "*" || ch === "+" || ch === "?") {
-    return { consumed: source[index + 1] === "?" ? 2 : 1 };
+  const consumed = source[index + 1] === "?" ? 2 : 1;
+  if (ch === "*") {
+    return { consumed, minRepeat: 0, maxRepeat: null };
+  }
+  if (ch === "+") {
+    return { consumed, minRepeat: 1, maxRepeat: null };
+  }
+  if (ch === "?") {
+    return { consumed, minRepeat: 0, maxRepeat: 1 };
   }
   if (ch !== "{") {
     return null;
   }
+
   let i = index + 1;
   while (i < source.length && /\d/.test(source[i])) {
     i += 1;
@@ -105,12 +211,18 @@ function readQuantifier(source: string, index: number): QuantifierRead | null {
   if (i === index + 1) {
     return null;
   }
+
+  const minRepeat = Number.parseInt(source.slice(index + 1, i), 10);
+  let maxRepeat: number | null = minRepeat;
   if (source[i] === ",") {
     i += 1;
+    const maxStart = i;
     while (i < source.length && /\d/.test(source[i])) {
       i += 1;
     }
+    maxRepeat = i === maxStart ? null : Number.parseInt(source.slice(maxStart, i), 10);
   }
+
   if (source[i] !== "}") {
     return null;
   }
@@ -118,7 +230,11 @@ function readQuantifier(source: string, index: number): QuantifierRead | null {
   if (source[i] === "?") {
     i += 1;
   }
-  return { consumed: i - index };
+  if (maxRepeat !== null && maxRepeat < minRepeat) {
+    return null;
+  }
+
+  return { consumed: i - index, minRepeat, maxRepeat };
 }
 
 export function compileSafeRegex(source: string, flags = ""): RegExp | null {