diff --git a/tests/Feature/Mcp/MediaUploadFlowTest.php b/tests/Feature/Mcp/MediaUploadFlowTest.php
new file mode 100644
index 00000000..65fbbe74
--- /dev/null
+++ b/tests/Feature/Mcp/MediaUploadFlowTest.php
@@ -0,0 +1,59 @@
+<?php
+
+declare(strict_types=1);
+
+use App\Enums\UserWorkspace\Role;
+use App\Mcp\Servers\TryPostServer;
+use App\Mcp\Tools\Post\AttachMediaFromUploadTool;
+use App\Mcp\Tools\Post\RequestMediaUploadTool;
+use App\Models\Post;
+use App\Models\User;
+use App\Models\Workspace;
+use Illuminate\Http\UploadedFile;
+use Illuminate\Support\Facades\Cache;
+use Illuminate\Support\Facades\Storage;
+use Illuminate\Testing\Fluent\AssertableJson;
+
+beforeEach(function () {
+    Storage::fake();
+    Cache::flush();
+
+    $this->user = User::factory()->create();
+    $this->workspace = Workspace::factory()->create(['user_id' => $this->user->id]);
+    $this->workspace->members()->attach($this->user->id, ['role' => Role::Member->value]);
+    $this->user->update(['current_workspace_id' => $this->workspace->id]);
+
+    $this->post = Post::factory()->create([
+        'workspace_id' => $this->workspace->id,
+        'user_id' => $this->user->id,
+    ]);
+});
+
+test('agent can request URL, client uploads, agent attaches to post', function () {
+    $uploadUrl = null;
+    $uploadToken = null;
+
+    TryPostServer::actingAs($this->user)
+        ->tool(RequestMediaUploadTool::class, [])
+        ->assertOk()
+        ->assertStructuredContent(function (AssertableJson $json) use (&$uploadUrl, &$uploadToken) {
+            $json->etc();
+            $uploadUrl = $json->toArray()['upload_url'];
+            $uploadToken = $json->toArray()['upload_token'];
+        });
+
+    expect($uploadUrl)->not->toBeNull();
+    expect($uploadToken)->not->toBeNull();
+
+    $file = UploadedFile::fake()->image('e2e.png', 64, 64);
+    $this->post($uploadUrl, ['media' => $file])->assertCreated();
+
+    TryPostServer::actingAs($this->user)
+        ->tool(AttachMediaFromUploadTool::class, [
+            'post_id' => $this->post->id,
+            'upload_token' => $uploadToken,
+        ])
+        ->assertOk();
+
+    expect($this->post->fresh()->media)->toHaveCount(1);
+});