@@ -87,18 +87,18 @@ back to the previous matching marker":
 [
     "# Changelog",
     "^",
-    "%% \\d+\\.\\d+\\.\\d+",
+    "%% ^\\d+\\.\\d+\\.\\d+$",
     "### Fixes",
     "### Features",
     "^"
 ]
 ```
 
 The simple form shown above is enough for most scenarios; if multiple loops are
-needed, the values `^^`, `^^^`, etc. can be used in conjunction. The special
-value `?` is supported with loops, but `*` and `+` are not supported and will
-result in undefined behavior. To avoid infinite loops, a violation is reported
-if more than 1,000 loops are performed.
+needed, the values `^^`, `^^^`, etc. can be used in conjunction. The prefix `%`
+and the special value `?` are supported with loops, but `*` and `+` are not and
+will result in undefined behavior. To avoid infinite loops, a violation is
+reported if more than 1,000 loops are performed.
 
 When an error is detected, this rule outputs the line number of the first
 problematic heading (otherwise, it outputs the last line number of the file).
 
@@ -1932,18 +1932,18 @@ back to the previous matching marker":
 [
     "# Changelog",
     "^",
-    "%% \\d+\\.\\d+\\.\\d+",
+    "%% ^\\d+\\.\\d+\\.\\d+$",
     "### Fixes",
     "### Features",
     "^"
 ]
 ```
 
 The simple form shown above is enough for most scenarios; if multiple loops are
-needed, the values `^^`, `^^^`, etc. can be used in conjunction. The special
-value `?` is supported with loops, but `*` and `+` are not supported and will
-result in undefined behavior. To avoid infinite loops, a violation is reported
-if more than 1,000 loops are performed.
+needed, the values `^^`, `^^^`, etc. can be used in conjunction. The prefix `%`
+and the special value `?` are supported with loops, but `*` and `+` are not and
+will result in undefined behavior. To avoid infinite loops, a violation is
+reported if more than 1,000 loops are performed.
 
 When an error is detected, this rule outputs the line number of the first
 problematic heading (otherwise, it outputs the last line number of the file).
 
@@ -98,18 +98,18 @@ back to the previous matching marker":
 [
     "# Changelog",
     "^",
-    "%% \\d+\\.\\d+\\.\\d+",
+    "%% ^\\d+\\.\\d+\\.\\d+$",
     "### Fixes",
     "### Features",
     "^"
 ]
 ```
 
 The simple form shown above is enough for most scenarios; if multiple loops are
-needed, the values `^^`, `^^^`, etc. can be used in conjunction. The special
-value `?` is supported with loops, but `*` and `+` are not supported and will
-result in undefined behavior. To avoid infinite loops, a violation is reported
-if more than 1,000 loops are performed.
+needed, the values `^^`, `^^^`, etc. can be used in conjunction. The prefix `%`
+and the special value `?` are supported with loops, but `*` and `+` are not and
+will result in undefined behavior. To avoid infinite loops, a violation is
+reported if more than 1,000 loops are performed.
 
 When an error is detected, this rule outputs the line number of the first
 problematic heading (otherwise, it outputs the last line number of the file).
 
@@ -4,16 +4,16 @@ import { addError, addErrorDetailIf } from "../helpers/helpers.cjs";
 import { getHeadingLevel, getHeadingText } from "../helpers/micromark-helpers.cjs";
 import { filterByTypesCached } from "./cache.mjs";
 
-export const headingsItemsRe = /^([*+?]|\^+|[#%]{1,6}\s+\S.*)$/u;
-const headingPartsRe = /^([#%]{1,6})\s+(\S.*)$/u;
+export const headingsItemsRe = /^(?:[*+?]|\^+|[#%]{1,6}\s+\S.*)$/u;
+const prefixedHeadingPartsRe = /^([#%]{1,6})\s+(\S.*)$/u;
 const loopHeadingRe = /^\^+$/u;
-const validExtraHeadingsRe = /^(?:\*|\^+)$/u;
+const canMatchNothingHeadingsRe = /^(?:\*|\^+)$/u;
 
 const headingIsExpected = (/** @type {string} */ actual, /** @type {string} */ expected, /** @type {boolean} */ matchCase) => {
   if (expected.startsWith("%")) {
     // Regular expression comparison
-    const [ , actualLevel, actualText ] = headingPartsRe.exec(actual) || [];
-    const [ , expectedLevel, expectedText ] = headingPartsRe.exec(expected) || [];
+    const [ , actualLevel, actualText ] = prefixedHeadingPartsRe.exec(actual) || [];
+    const [ , expectedLevel, expectedText ] = prefixedHeadingPartsRe.exec(expected) || [];
     return (
       (actualLevel.length === expectedLevel.length) &&
       // eslint-disable-next-line unicorn/no-unreadable-new-expression
@@ -36,14 +36,13 @@ export default {
     /** @type {string[] | null | undefined} */
     const headings = params.config.headings;
     if (!headings) {
-      // Nothing to check
       return;
     }
     const requiredHeadings = headings.map((heading) => headingsItemsRe.test(heading) ? heading : "[Invalid syntax]");
-    const matchCase = params.config.match_case || false;
+    const matchCase = Boolean(params.config.match_case);
     let i = 0;
-    let loopsRemaining = 1000;
-    let matchAny = false;
+    let loopsAllowed = 1000;
+    let allowAnyMatchFallback = false;
     let hasError = false;
     const getExpected = (/** @type {boolean} */ skipLoopHeadings) => {
       let expected = null;
@@ -54,72 +53,70 @@ export default {
       return expected;
     };
     for (const heading of filterByTypesCached([ "atxHeading", "setextHeading" ])) {
-      if (!hasError) {
-        const headingText = getHeadingText(heading);
-        const headingLevel = getHeadingLevel(heading);
-        const actual = `${"".padEnd(headingLevel, "#")} ${headingText}`;
-        let expected = getExpected(false);
-
-        if (expected.startsWith("^")) {
-          const save = i;
-          const nextExpected = getExpected(true);
-          if (headingIsExpected(actual, nextExpected, matchCase)) {
-            expected = nextExpected;
-          } else {
-            for (let j = save - 1; j--; j >= 0) {
-              if (requiredHeadings[j] === expected) {
-                i = j + 1;
-                expected = getExpected(false);
-                loopsRemaining--;
-                break;
-              }
-            }
-            if (i < 0) {
-              // Nothing to skip back to; continue from current location
-              i = save;
+      const headingText = getHeadingText(heading);
+      const headingLevel = getHeadingLevel(heading);
+      const actual = `${"".padEnd(headingLevel, "#")} ${headingText}`;
+      let expected = getExpected(false);
+      if (expected.startsWith("^")) {
+        // Handle loop
+        const current = i;
+        const nextExpected = getExpected(true);
+        if (headingIsExpected(actual, nextExpected, matchCase)) {
+          // No need to loop (again)
+          expected = nextExpected;
+        } else {
+          // Loop to previous matching marker
+          let j = current - 1;
+          for (; j--; j >= 0) {
+            if (requiredHeadings[j] === expected) {
+              i = j + 1;
+              expected = getExpected(false);
+              loopsAllowed--;
+              break;
             }
           }
-        }
-
-        if (loopsRemaining < 0) {
-          addError(onError, heading.startLine, "Too many loops");
-          hasError = true;
-        } else if (expected === "*") {
-          const nextExpected = getExpected(false);
-          if (!headingIsExpected(actual, nextExpected, matchCase)) {
-            matchAny = true;
-            i--;
+          if (j < 0) {
+            expected = nextExpected;
           }
-        } else if (expected === "+") {
-          matchAny = true;
-        } else if (expected === "?") {
-          // Allow current, match next
-        } else if (headingIsExpected(actual, expected, matchCase)) {
-          matchAny = false;
-        } else if (matchAny) {
+        }
+      }
+      if (loopsAllowed < 0) {
+        // Too many loops
+        addError(onError, heading.startLine, "Too many loops");
+        hasError = true;
+        break;
+      } else if (expected === "*") {
+        // Handle "zero or more of anything"
+        const nextExpected = getExpected(true);
+        if (!headingIsExpected(actual, nextExpected, matchCase)) {
+          allowAnyMatchFallback = true;
           i--;
-        } else {
-          addErrorDetailIf(
-            onError,
-            heading.startLine,
-            expected,
-            actual
-          );
-          hasError = true;
         }
+      } else if (expected === "+") {
+        // Handle "one or more of anything"
+        allowAnyMatchFallback = true;
+      } else if (expected === "?") {
+        // Handle "exactly one of anything"
+      } else if (headingIsExpected(actual, expected, matchCase)) {
+        // Handle successful match
+        allowAnyMatchFallback = false;
+      } else if (allowAnyMatchFallback) {
+        // Handle "anything" match by restoring index
+        i--;
+      } else {
+        // Report heading mismatch
+        addErrorDetailIf(onError, heading.startLine, expected, actual);
+        hasError = true;
+        break;
       }
     }
-    const extraHeadings = requiredHeadings.slice(i);
+    const remainingRequiredHeadings = requiredHeadings.slice(i).filter((heading) => !canMatchNothingHeadingsRe.test(heading));
     if (
       !hasError &&
-      !extraHeadings.every((heading) => validExtraHeadingsRe.test(heading))
+      (remainingRequiredHeadings.length > 0)
     ) {
-      addErrorDetailIf(
-        onError,
-        params.lines.length,
-        requiredHeadings[i],
-        "[End of file]"
-      );
+      // Report unmatched heading(s)
+      addErrorDetailIf(onError, params.lines.length, remainingRequiredHeadings[0], "[End of file]");
     }
   }
 };
@@ -3265,7 +3265,7 @@
               ],
               "items": {
                 "type": "string",
-                "pattern": "^([*+?]|\\^+|[#%]{1,6}\\s+\\S.*)$"
+                "pattern": "^(?:[*+?]|\\^+|[#%]{1,6}\\s+\\S.*)$"
               },
               "default": null
             },
@@ -3317,7 +3317,7 @@
               ],
               "items": {
                 "type": "string",
-                "pattern": "^([*+?]|\\^+|[#%]{1,6}\\s+\\S.*)$"
+                "pattern": "^(?:[*+?]|\\^+|[#%]{1,6}\\s+\\S.*)$"
               },
               "default": null
             },
 
@@ -3265,7 +3265,7 @@
               ],
               "items": {
                 "type": "string",
-                "pattern": "^([*+?]|\\^+|[#%]{1,6}\\s+\\S.*)$"
+                "pattern": "^(?:[*+?]|\\^+|[#%]{1,6}\\s+\\S.*)$"
               },
               "default": null
             },
@@ -3317,7 +3317,7 @@
               ],
               "items": {
                 "type": "string",
-                "pattern": "^([*+?]|\\^+|[#%]{1,6}\\s+\\S.*)$"
+                "pattern": "^(?:[*+?]|\\^+|[#%]{1,6}\\s+\\S.*)$"
               },
               "default": null
             },