diff --git a/src/Tempest/Http/src/IsRequest.php b/src/Tempest/Http/src/IsRequest.php
index 55f4eeeff..8631c1f2e 100644
--- a/src/Tempest/Http/src/IsRequest.php
+++ b/src/Tempest/Http/src/IsRequest.php
@@ -27,6 +27,7 @@ public function __construct(
     ) {
         $this->path ??= $this->resolvePath();
         $this->query ??= $this->resolveQuery();
+        $this->files ??= [];
     }
 
     public function get(string $key, mixed $default = null): mixed
diff --git a/src/Tempest/Http/src/Mappers/PsrRequestToRequestMapper.php b/src/Tempest/Http/src/Mappers/PsrRequestToRequestMapper.php
index 7e8e40981..c66ae5399 100644
--- a/src/Tempest/Http/src/Mappers/PsrRequestToRequestMapper.php
+++ b/src/Tempest/Http/src/Mappers/PsrRequestToRequestMapper.php
@@ -54,6 +54,7 @@ public function map(mixed $from, mixed $to): array|object
             'query' => $query,
             'files' => $uploads,
             ...$data,
+            ...$uploads,
         ])->to($requestClass);
 
         $validator = new Validator();
diff --git a/src/Tempest/Http/src/Mappers/RequestToPsrRequestMapper.php b/src/Tempest/Http/src/Mappers/RequestToPsrRequestMapper.php
index cb5baecde..40476aba6 100644
--- a/src/Tempest/Http/src/Mappers/RequestToPsrRequestMapper.php
+++ b/src/Tempest/Http/src/Mappers/RequestToPsrRequestMapper.php
@@ -27,6 +27,7 @@ public function map(mixed $from, mixed $to): PsrRequest
             cookieParams: $from->getCookies(),
             queryParams: $from->getQuery(),
             parsedBody: $from->getBody(),
+            uploadedFiles: $from->getFiles()
         );
     }
 }
diff --git a/src/Tempest/Mapper/src/Mappers/ArrayToObjectMapper.php b/src/Tempest/Mapper/src/Mappers/ArrayToObjectMapper.php
index dfce572eb..78f59d84f 100644
--- a/src/Tempest/Mapper/src/Mappers/ArrayToObjectMapper.php
+++ b/src/Tempest/Mapper/src/Mappers/ArrayToObjectMapper.php
@@ -160,9 +160,9 @@ private function resolveValueFromArray(
 
         $caster = $this->casterFactory->forProperty($property);
 
-        foreach ($data as $item) {
+        foreach ($data as $key => $item) {
             if (! is_array($item)) {
-                $values[] = $caster?->cast($item) ?? $item;
+                $values[$key] = $caster?->cast($item) ?? $item;
 
                 continue;
             }
diff --git a/tests/Fixtures/Modules/Books/Requests/CreateBookRequest.php b/tests/Fixtures/Modules/Books/Requests/CreateBookRequest.php
index 245cb9d9d..48db7fc94 100644
--- a/tests/Fixtures/Modules/Books/Requests/CreateBookRequest.php
+++ b/tests/Fixtures/Modules/Books/Requests/CreateBookRequest.php
@@ -6,10 +6,13 @@
 
 use Tempest\Http\IsRequest;
 use Tempest\Http\Request;
+use Tempest\Http\Upload;
 
 final class CreateBookRequest implements Request
 {
     use IsRequest;
 
     public string $title;
+
+    public Upload $cover;
 }
diff --git a/tests/Integration/Mapper/PsrRequestToRequestMapperTest.php b/tests/Integration/Mapper/PsrRequestToRequestMapperTest.php
index 163a2d2b8..0a6c1f634 100644
--- a/tests/Integration/Mapper/PsrRequestToRequestMapperTest.php
+++ b/tests/Integration/Mapper/PsrRequestToRequestMapperTest.php
@@ -10,6 +10,8 @@
 use Tempest\Http\Request;
 use Tempest\Http\Upload;
 use Tempest\Mapper\Exceptions\MissingValuesException;
+use function Tempest\Support\arr;
+use Tests\Tempest\Fixtures\Modules\Books\Requests\CreateBookRequest;
 use Tests\Tempest\Fixtures\Modules\Posts\PostRequest;
 use Tests\Tempest\Integration\FrameworkIntegrationTestCase;
 
@@ -113,4 +115,32 @@ public function test_files(): void
         $this->assertSame('hello', $upload->getClientFilename());
         $this->assertSame('application/octet-stream', $upload->getClientMediaType());
     }
+
+    public function test_map_upload_file_into_request_property(): void
+    {
+        $currentPath = __DIR__ . '/Fixtures/upload.txt';
+
+        $mapper = new PsrRequestToRequestMapper();
+
+        $psrRequest = $this->http->makePsrRequest(
+            uri: '/books',
+            body: ['title' => 'Timeline Taxi'],
+            files: ['cover' => new UploadedFile(
+                streamOrFile: $currentPath,
+                size: null,
+                errorStatus: UPLOAD_ERR_OK,
+            )]
+        );
+
+        $request = $mapper->map(
+            from: $psrRequest,
+            to: CreateBookRequest::class
+        );
+
+        $this->assertInstanceOf(CreateBookRequest::class, $request);
+        $this->assertInstanceOf(Upload::class, $request->cover);
+
+        $this->assertEquals('cover', array_key_first($request->getFiles()));
+        $this->assertTrue(arr($request->getFiles())->isAssoc());
+    }
 }