diff --git a/src/Node/Expression/Binary/MatchesBinary.php b/src/Node/Expression/Binary/MatchesBinary.php
index 4669044e0..ba25313c0 100644
--- a/src/Node/Expression/Binary/MatchesBinary.php
+++ b/src/Node/Expression/Binary/MatchesBinary.php
@@ -12,9 +12,27 @@
 namespace Twig\Node\Expression\Binary;
 
 use Twig\Compiler;
+use Twig\Error\SyntaxError;
+use Twig\Node\Node;
+use Twig\Node\Expression\ConstantExpression;
 
 class MatchesBinary extends AbstractBinary
 {
+    public function __construct(Node $left, Node $right, int $lineno)
+    {
+        if ($right instanceof ConstantExpression) {
+            $regexp = $right->getAttribute('value');
+            set_error_handler(static fn ($t, $m) => throw new SyntaxError(\sprintf('Regexp "%s" passed to "matches" is not valid: %s.', $regexp, substr($m, 14)), $lineno));
+            try {
+                preg_match($regexp, '');
+            } finally {
+                restore_error_handler();
+            }
+        }
+
+        parent::__construct($left, $right, $lineno);
+    }
+
     public function compile(Compiler $compiler): void
     {
         $compiler
diff --git a/src/Test/IntegrationTestCase.php b/src/Test/IntegrationTestCase.php
index 67c168090..b66c17fd2 100644
--- a/src/Test/IntegrationTestCase.php
+++ b/src/Test/IntegrationTestCase.php
@@ -245,7 +245,7 @@ abstract class IntegrationTestCase extends TestCase
                 $output = trim($template->render(eval($match[1].';')), "\n ");
             } catch (\Exception $e) {
                 if (false !== $exception) {
-                    $this->assertSame(trim($exception), trim(\sprintf('%s: %s', \get_class($e), $e->getMessage())));
+                    $this->assertStringMatchesFormat(trim($exception), trim(\sprintf('%s: %s', \get_class($e), $e->getMessage())));
 
                     return;
                 }
diff --git a/tests/Fixtures/expressions/matches.test b/tests/Fixtures/expressions/matches.test
index 8f5e3669e..00a5702b4 100644
--- a/tests/Fixtures/expressions/matches.test
+++ b/tests/Fixtures/expressions/matches.test
@@ -2,7 +2,9 @@
 Twig supports the "matches" operator
 --TEMPLATE--
 {{ 'foo' matches '/o/' ? 'OK' : 'KO' }}
+{{ 'foo' matches '/o/'|lower ? 'OK' : 'KO' }}
 {{ 'foo' matches '/^fo/' ? 'OK' : 'KO' }}
+{{ 'foo' matches '/^' ~ 'fo/' ? 'OK' : 'KO' }}
 {{ 'foo' matches '/O/i' ? 'OK' : 'KO' }}
 {{ null matches '/o/' }}
 --DATA--
@@ -11,4 +13,6 @@ return []
 OK
 OK
 OK
+OK
+OK
 0
diff --git a/tests/Fixtures/expressions/matches_error.test b/tests/Fixtures/expressions/matches_error_compilation.test
similarity index 53%
rename from tests/Fixtures/expressions/matches_error.test
rename to tests/Fixtures/expressions/matches_error_compilation.test
index 1220eb422..c251be134 100644
--- a/tests/Fixtures/expressions/matches_error.test
+++ b/tests/Fixtures/expressions/matches_error_compilation.test
@@ -5,4 +5,4 @@ Twig supports the "matches" operator with a great error message
 --DATA--
 return []
 --EXCEPTION--
-Twig\Error\RuntimeError: Regexp "/o" passed to "matches" is not valid: No ending delimiter '/' found in "index.twig" at line 2
+Twig\Error\SyntaxError: Regexp "/o" passed to "matches" is not valid: No ending delimiter '/' found in "index.twig" at line 2.
diff --git a/tests/Fixtures/expressions/matches_error_runtime.test b/tests/Fixtures/expressions/matches_error_runtime.test
new file mode 100644
index 000000000..4a2bb5943
--- /dev/null
+++ b/tests/Fixtures/expressions/matches_error_runtime.test
@@ -0,0 +1,8 @@
+--TEST--
+Twig supports the "matches" operator with a great error message
+--TEMPLATE--
+{{ 'foo' matches 1 + 2 }}
+--DATA--
+return []
+--EXCEPTION--
+Twig\Error\RuntimeError: Regexp "3" passed to "matches" is not valid: Delimiter must not be alphanumeric%sbackslash%sin "index.twig" at line 2