diff --git a/app/Mcp/Servers/TryPostServer.php b/app/Mcp/Servers/TryPostServer.php
index 6bd9df35..d61aa92c 100644
--- a/app/Mcp/Servers/TryPostServer.php
+++ b/app/Mcp/Servers/TryPostServer.php
@@ -20,6 +20,7 @@
 use App\Mcp\Tools\Post\ListPostsTool;
 use App\Mcp\Tools\Post\PreviewPostTool;
 use App\Mcp\Tools\Post\PublishPostTool;
+use App\Mcp\Tools\Post\RequestMediaUploadTool;
 use App\Mcp\Tools\Post\UpdatePostTool;
 use App\Mcp\Tools\Signature\CreateSignatureTool;
 use App\Mcp\Tools\Signature\DeleteSignatureTool;
@@ -50,6 +51,7 @@ class TryPostServer extends Server
         PreviewPostTool::class,
         DeletePostTool::class,
         AttachMediaFromUrlTool::class,
+        RequestMediaUploadTool::class,
         GetPostMetricsTool::class,
 
         // Platforms (read-only metadata)
diff --git a/app/Mcp/Tools/Post/RequestMediaUploadTool.php b/app/Mcp/Tools/Post/RequestMediaUploadTool.php
new file mode 100644
index 00000000..e61dcd84
--- /dev/null
+++ b/app/Mcp/Tools/Post/RequestMediaUploadTool.php
@@ -0,0 +1,47 @@
+<?php
+
+declare(strict_types=1);
+
+namespace App\Mcp\Tools\Post;
+
+use Carbon\CarbonImmutable;
+use Illuminate\Contracts\JsonSchema\JsonSchema;
+use Illuminate\Support\Facades\URL;
+use Illuminate\Support\Str;
+use Laravel\Mcp\Request;
+use Laravel\Mcp\Response;
+use Laravel\Mcp\ResponseFactory;
+use Laravel\Mcp\Server\Attributes\Description;
+use Laravel\Mcp\Server\Tool;
+
+#[Description('Issue a one-shot signed POST URL that lets the user upload a local file (image up to 10 MB, video up to 50 MB hard cap) directly to this workspace. Returns an upload_token and upload_url. Hand the URL to the user (e.g. as a curl command with `-F media=@path/to/file`) or to the MCP client. After upload, call AttachMediaFromUploadTool(post_id, upload_token) to attach the result to a post.')]
+class RequestMediaUploadTool extends Tool
+{
+    public function handle(Request $request): Response|ResponseFactory
+    {
+        $user = $request->user();
+        $workspaceId = $user->current_workspace_id;
+
+        $token = (string) Str::uuid();
+        $expiresAt = CarbonImmutable::now()->addMinutes(15);
+
+        $uploadUrl = URL::temporarySignedRoute(
+            'api.uploads.store',
+            $expiresAt,
+            ['token' => $token, 'ws' => $workspaceId],
+        );
+
+        return Response::structured([
+            'upload_token' => $token,
+            'upload_url' => $uploadUrl,
+            'expires_at' => $expiresAt->toIso8601String(),
+            'max_bytes' => 52428800,
+            'field_name' => 'media',
+        ]);
+    }
+
+    public function schema(JsonSchema $schema): array
+    {
+        return [];
+    }
+}
diff --git a/tests/Feature/Mcp/RequestMediaUploadToolTest.php b/tests/Feature/Mcp/RequestMediaUploadToolTest.php
new file mode 100644
index 00000000..8ce7afbc
--- /dev/null
+++ b/tests/Feature/Mcp/RequestMediaUploadToolTest.php
@@ -0,0 +1,72 @@
+<?php
+
+declare(strict_types=1);
+
+use App\Enums\UserWorkspace\Role;
+use App\Mcp\Servers\TryPostServer;
+use App\Mcp\Tools\Post\RequestMediaUploadTool;
+use App\Models\User;
+use App\Models\Workspace;
+use Illuminate\Support\Facades\URL;
+use Illuminate\Testing\Fluent\AssertableJson;
+
+beforeEach(function () {
+    $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]);
+});
+
+test('returns a single-use signed upload URL', function () {
+    $response = TryPostServer::actingAs($this->user)
+        ->tool(RequestMediaUploadTool::class, []);
+
+    $response->assertOk()
+        ->assertStructuredContent(function (AssertableJson $json) {
+            $json->has('upload_token')
+                ->has('upload_url')
+                ->has('expires_at')
+                ->where('max_bytes', 52428800)
+                ->where('field_name', 'media')
+                ->etc();
+        });
+});
+
+test('signed URL is valid against the api.uploads.store route', function () {
+    $uploadUrl = null;
+
+    TryPostServer::actingAs($this->user)
+        ->tool(RequestMediaUploadTool::class, [])
+        ->assertOk()
+        ->assertStructuredContent(function (AssertableJson $json) use (&$uploadUrl) {
+            $json->etc();
+            $uploadUrl = $json->toArray()['upload_url'];
+        });
+
+    expect(URL::hasValidSignature(
+        request()->create($uploadUrl, 'POST'),
+    ))->toBeTrue();
+});
+
+test('each call returns a distinct upload_token', function () {
+    $firstToken = null;
+    $secondToken = null;
+
+    TryPostServer::actingAs($this->user)
+        ->tool(RequestMediaUploadTool::class, [])
+        ->assertOk()
+        ->assertStructuredContent(function (AssertableJson $json) use (&$firstToken) {
+            $json->etc();
+            $firstToken = $json->toArray()['upload_token'];
+        });
+
+    TryPostServer::actingAs($this->user)
+        ->tool(RequestMediaUploadTool::class, [])
+        ->assertOk()
+        ->assertStructuredContent(function (AssertableJson $json) use (&$secondToken) {
+            $json->etc();
+            $secondToken = $json->toArray()['upload_token'];
+        });
+
+    expect($firstToken)->not->toBe($secondToken);
+});