diff --git a/CHANGELOG b/CHANGELOG
index a3b240fff70..991e99dfca5 100644
--- a/CHANGELOG
+++ b/CHANGELOG
@@ -1,5 +1,6 @@
 # 3.29.0 (2026-XX-XX)
 
+ * Fix the `matches` operator silently treating PCRE execution errors as non-matches
  * Add the `HtmlExtension::htmlAttrValue()` method to resolve a single HTML attribute value the way the `html_attr` function renders it
  * Fix `html_attr` JSON encoding a `Stringable` value in a `data-*` attribute instead of using its string representation
  * Add documentation comments to attach metadata to nodes (experimental)
diff --git a/src/Extension/CoreExtension.php b/src/Extension/CoreExtension.php
index e14b8b6978b..8d811518cef 100644
--- a/src/Extension/CoreExtension.php
+++ b/src/Extension/CoreExtension.php
@@ -1188,7 +1188,7 @@ public static function compare($a, $b)
     }
 
     /**
-     * @throws RuntimeError When an invalid pattern is used
+     * @throws RuntimeError When the regular expression cannot be evaluated
      *
      * @internal
      */
@@ -1198,7 +1198,11 @@ public static function matches(string $regexp, ?string $str): int
             throw new RuntimeError(\sprintf('Regexp "%s" passed to "matches" is not valid', $regexp).substr($m, 12));
         });
         try {
-            return preg_match($regexp, $str ?? '');
+            if (false === $result = preg_match($regexp, $str ?? '')) {
+                throw new RuntimeError(\sprintf('Regexp "%s" passed to "matches" failed: %s.', $regexp, preg_last_error_msg()));
+            }
+
+            return $result;
         } finally {
             restore_error_handler();
         }
diff --git a/tests/Fixtures/expressions/matches_error_execution.test b/tests/Fixtures/expressions/matches_error_execution.test
new file mode 100644
index 00000000000..79e4014f0cc
--- /dev/null
+++ b/tests/Fixtures/expressions/matches_error_execution.test
@@ -0,0 +1,8 @@
+--TEST--
+Twig reports PCRE execution failures for the "matches" operator
+--TEMPLATE--
+{{ subject matches regexp }}
+--DATA--
+return ['subject' => 'aX', 'regexp' => '~(*LIMIT_MATCH=1)^(a+)+$~'];
+--EXCEPTION--
+Twig\Error\RuntimeError: Regexp "~(*LIMIT_MATCH=1)^(a+)+$~" passed to "matches" failed: Backtrack limit exhausted in "index.twig" at line 2.