diff --git a/packages/http/src/IsRequest.php b/packages/http/src/IsRequest.php
index 930b07dce..493216508 100644
--- a/packages/http/src/IsRequest.php
+++ b/packages/http/src/IsRequest.php
@@ -38,7 +38,7 @@ trait IsRequest
     #[SkipValidation]
     private(set) array $query;
 
-    /** @var \Tempest\Http\Upload[] */
+    /** @var array<array-key, \Tempest\Http\Upload|array> */
     #[SkipValidation]
     private(set) array $files;
 
diff --git a/packages/http/src/Mappers/PsrRequestToGenericRequestMapper.php b/packages/http/src/Mappers/PsrRequestToGenericRequestMapper.php
index 3ba06ebe0..c30eecbf4 100644
--- a/packages/http/src/Mappers/PsrRequestToGenericRequestMapper.php
+++ b/packages/http/src/Mappers/PsrRequestToGenericRequestMapper.php
@@ -51,10 +51,7 @@ public function map(mixed $from, mixed $to): GenericRequest
 
         parse_str($from->getUri()->getQuery(), $query);
 
-        $uploads = array_map(
-            fn (UploadedFileInterface $uploadedFile) => new Upload($uploadedFile),
-            $from->getUploadedFiles(),
-        );
+        $uploads = $this->createUploads($from->getUploadedFiles());
 
         return map([
             'method' => $this->requestMethod($from, $data),
@@ -88,6 +85,22 @@ public function map(mixed $from, mixed $to): GenericRequest
             ->to(GenericRequest::class);
     }
 
+    /**
+     * Array-style file inputs, such as `files[]`, are exposed by PSR-7 as nested arrays.
+     *
+     * @param array<array-key, UploadedFileInterface|array> $uploadedFiles
+     * @return array<array-key, Upload|array>
+     */
+    private function createUploads(array $uploadedFiles): array
+    {
+        return array_map(
+            fn (UploadedFileInterface|array $uploadedFile) => $uploadedFile instanceof UploadedFileInterface
+                ? new Upload($uploadedFile)
+                : $this->createUploads($uploadedFile),
+            $uploadedFiles,
+        );
+    }
+
     private function requestMethod(PsrRequest $request, array $data): Method
     {
         $originalMethod = Method::from($request->getMethod());
diff --git a/packages/http/src/Request.php b/packages/http/src/Request.php
index 7193d4f57..2d1c373cc 100644
--- a/packages/http/src/Request.php
+++ b/packages/http/src/Request.php
@@ -22,7 +22,7 @@ interface Request
 
     public array $query { get; }
 
-    /** @var \Tempest\Http\Upload[] $files */
+    /** @var array<array-key, \Tempest\Http\Upload|array> $files */
     public array $files { get; }
 
     /** @var Cookie[] $cookies */
diff --git a/tests/Integration/Route/PsrRequestToGenericRequestMapperTest.php b/tests/Integration/Route/PsrRequestToGenericRequestMapperTest.php
index d9c18fea0..e2311e48f 100644
--- a/tests/Integration/Route/PsrRequestToGenericRequestMapperTest.php
+++ b/tests/Integration/Route/PsrRequestToGenericRequestMapperTest.php
@@ -106,6 +106,31 @@ public function files(): void
         $this->assertSame('application/octet-stream', $upload->getClientMediaType());
     }
 
+    #[Test]
+    public function nested_files(): void
+    {
+        /** @var GenericRequest $request */
+        $request = $this->mapper->map(
+            from: $this->http->makePsrRequest('/', files: [
+                'avatar' => $this->createUploadedFile('avatar.png'),
+                'documents' => [
+                    $this->createUploadedFile('one.txt'),
+                    'contract' => $this->createUploadedFile('contract.pdf'),
+                ],
+            ]),
+            to: Request::class,
+        );
+
+        $this->assertInstanceOf(Upload::class, $request->files['avatar']);
+        $this->assertSame('avatar.png', $request->files['avatar']->getClientFilename());
+
+        $this->assertInstanceOf(Upload::class, $request->files['documents'][0]);
+        $this->assertSame('one.txt', $request->files['documents'][0]->getClientFilename());
+
+        $this->assertInstanceOf(Upload::class, $request->files['documents']['contract']);
+        $this->assertSame('contract.pdf', $request->files['documents']['contract']->getClientFilename());
+    }
+
     #[Test]
     public function body_field_in_body(): void
     {
@@ -144,4 +169,14 @@ public function unencrypted_cookies_are_discarded(): void
         $this->assertSame($cookies['foo']->expiresAt, -1);
         $this->assertSame($cookies['foo']->value, '');
     }
+
+    private function createUploadedFile(string $filename): UploadedFile
+    {
+        return new UploadedFile(
+            streamOrFile: new Stream('php://temp', 'r+'),
+            size: 0,
+            errorStatus: UPLOAD_ERR_OK,
+            clientFilename: $filename,
+        );
+    }
 }