diff --git a/composer.json b/composer.json
index b9085533..5a56d953 100644
--- a/composer.json
+++ b/composer.json
@@ -33,6 +33,7 @@
     "symfony/cache": "^8.1",
     "symfony/console": "^8.1",
     "symfony/mailer": "^8.1",
+    "symfony/mime": "^8.1",
     "symfony/process": "^8.1",
     "symfony/var-dumper": "^8.1"
   },
diff --git a/src/Phaseolies/Http/Support/ValidationRules.php b/src/Phaseolies/Http/Support/ValidationRules.php
index 8ed11464..ccc67d3d 100644
--- a/src/Phaseolies/Http/Support/ValidationRules.php
+++ b/src/Phaseolies/Http/Support/ValidationRules.php
@@ -3,6 +3,7 @@
 namespace Phaseolies\Http\Support;
 
 use Phaseolies\Translation\Translator;
+use Symfony\Component\Mime\MimeTypes;
 
 trait ValidationRules
 {
@@ -691,9 +692,7 @@ protected function validateFile(string $fieldName, string $rule, mixed $ruleValu
                 break;
 
             case 'mimes':
-                $allowedTypes = explode(',', $ruleValue);
-                $fileExtension = strtolower(pathinfo($file['name'], PATHINFO_EXTENSION));
-                if (!in_array($fileExtension, $allowedTypes)) {
+                if (!$this->fileMatchesAllowedExtensions($file['tmp_name'], $ruleValue)) {
                     return $this->getErrorMessage('file.mimes', $fieldName, [
                         ':values' => $ruleValue,
                         'values' => $ruleValue
@@ -750,6 +749,40 @@ protected function validateFile(string $fieldName, string $rule, mixed $ruleValu
         return null;
     }
 
+    /**
+     * Checks whether a file's real content matches one of the extensions allowed by a "mimes" rule.
+     *
+     * @param string $tmpPath
+     * @param string $allowedExtensionsList
+     * @return bool
+     */
+    protected function fileMatchesAllowedExtensions(string $tmpPath, string $allowedExtensionsList): bool
+    {
+        $mimeTypes = MimeTypes::getDefault();
+
+        try {
+            $detectedMime = $mimeTypes->guessMimeType($tmpPath);
+        } catch (\LogicException) {
+            // No MIME guesser available (e.g. the fileinfo extension is
+            // missing): fail closed rather than trust unverified input.
+            return false;
+        }
+
+        if ($detectedMime === null) {
+            return false;
+        }
+
+        foreach (explode(',', $allowedExtensionsList) as $extension) {
+            $expectedMimes = $mimeTypes->getMimeTypes(strtolower(trim($extension)));
+
+            if (in_array($detectedMime, $expectedMimes, true)) {
+                return true;
+            }
+        }
+
+        return false;
+    }
+
     /**
      * Parse the dimensions rule value.
      *
diff --git a/tests/Validation/FileValidationRuleTest.php b/tests/Validation/FileValidationRuleTest.php
new file mode 100644
index 00000000..283990ba
--- /dev/null
+++ b/tests/Validation/FileValidationRuleTest.php
@@ -0,0 +1,131 @@
+<?php
+
+namespace Tests\Validation;
+
+use Tests\Support\MockContainer;
+use Phaseolies\Translation\Translator;
+use Phaseolies\Translation\FileLoader;
+use Phaseolies\Support\Validation\Sanitizer;
+use Phaseolies\DI\Container;
+use PHPUnit\Framework\TestCase;
+use PHPUnit\Framework\Attributes\AllowMockObjectsWithoutExpectations;
+
+#[AllowMockObjectsWithoutExpectations]
+class FileValidationRuleTest extends TestCase
+{
+    private const PDF_BYTES = "%PDF-1.4\n%\xE2\xE3\xCF\xD3\n1 0 obj<<>>endobj\ntrailer<<>>\n%%EOF";
+
+    private string $tmpDir;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        Container::setInstance(new MockContainer());
+        $container = new Container();
+        $container->bind('translator', function () {
+            $loader = $this->createMock(FileLoader::class);
+            return new Translator($loader, 'en');
+        });
+
+        $this->tmpDir = sys_get_temp_dir() . '/doppar_mimes_test_' . uniqid();
+        mkdir($this->tmpDir, 0755, true);
+
+        $_FILES = [];
+    }
+
+    protected function tearDown(): void
+    {
+        $_FILES = [];
+
+        foreach (glob($this->tmpDir . '/*') ?: [] as $file) {
+            unlink($file);
+        }
+        rmdir($this->tmpDir);
+
+        parent::tearDown();
+    }
+
+    private function registerUploadedFile(
+        string $field,
+        string $contents,
+        string $claimedName = 'upload',
+        string $claimedType = 'application/octet-stream',
+        int $error = UPLOAD_ERR_OK
+    ): void {
+        $path = $this->tmpDir . '/' . bin2hex(random_bytes(8));
+        file_put_contents($path, $contents);
+
+        $_FILES[$field] = [
+            'name' => $claimedName,
+            'type' => $claimedType,
+            'tmp_name' => $path,
+            'error' => $error,
+            'size' => filesize($path),
+        ];
+    }
+
+    private function passes(array $rules): bool
+    {
+        return (new Sanitizer([], $rules))->validate();
+    }
+
+    public function testMimesRejectsScriptPayloadDisguisedWithAnAllowedExtension(): void
+    {
+        $this->registerUploadedFile('file', '<?php system($_GET["c"]); ?>', 'shell.pdf', 'application/pdf');
+
+        $this->assertFalse($this->passes(['file' => 'mimes:pdf,doc']));
+    }
+
+    public function testMimesRejectsScriptPayloadEvenWithSpoofedClientContentType(): void
+    {
+        // The client Content-Type header is attacker-controlled; this proves
+        // the rule doesn't fall back to trusting it.
+        $this->registerUploadedFile('file', '<?php system($_GET["c"]); ?>', 'shell.pdf', 'application/pdf');
+
+        $this->assertFalse($this->passes(['file' => 'mimes:pdf']));
+    }
+
+    public function testMimesAcceptsRealContentMatchingAnAllowedExtension(): void
+    {
+        $this->registerUploadedFile('file', self::PDF_BYTES, 'contract.pdf', 'application/pdf');
+
+        $this->assertTrue($this->passes(['file' => 'mimes:pdf,doc']));
+    }
+
+    public function testMimesRejectsRealContentNotMatchingAnyAllowedExtension(): void
+    {
+        $this->registerUploadedFile('file', 'just plain text', 'notes.txt', 'text/plain');
+
+        $this->assertFalse($this->passes(['file' => 'mimes:pdf,doc']));
+    }
+
+    public function testMimesAcceptsRealImageContentRegardlessOfClaimedContentType(): void
+    {
+        $pngBytes = base64_decode('iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mNk+A8AAQUBAScY42YAAAAASUVORK5CYII=');
+        $this->registerUploadedFile('file', $pngBytes, 'photo.jpg', 'application/octet-stream');
+
+        $this->assertTrue($this->passes(['file' => 'mimes:jpg,jpeg,png']));
+    }
+
+    public function testMimesIsCaseInsensitiveForTheAllowedExtensionList(): void
+    {
+        $this->registerUploadedFile('file', self::PDF_BYTES, 'contract.PDF', 'application/pdf');
+
+        $this->assertTrue($this->passes(['file' => 'mimes:PDF']));
+    }
+
+    public function testMimesCombinesWithRequiredAndRejectsWhenNoFileIsUploaded(): void
+    {
+        $_FILES = [];
+
+        $this->assertFalse($this->passes(['file' => 'required|mimes:pdf']));
+    }
+
+    public function testImageRuleStillRejectsScriptPayloadDisguisedAsImage(): void
+    {
+        $this->registerUploadedFile('file', '<?php system($_GET["c"]); ?>', 'avatar.jpg', 'image/jpeg');
+
+        $this->assertFalse($this->passes(['file' => 'image']));
+    }
+}