diff --git a/app/Http/Requests/Task/UploadTaskRequest.php b/app/Http/Requests/Task/UploadTaskRequest.php
index 66a0f8008d61..6b7d96ef048b 100644
--- a/app/Http/Requests/Task/UploadTaskRequest.php
+++ b/app/Http/Requests/Task/UploadTaskRequest.php
@@ -30,11 +30,22 @@ class UploadTaskRequest extends Request
 
     public function rules()
     {
-        $rules = [
-            'documents' => 'bail|sometimes|file|mimes:csv,png,ai,jpeg,tiff,pdf,gif,psd,txt,doc,xls,ppt,xlsx,docx,pptx|max:2000000',
-            'is_public' => 'sometimes|boolean',
-        ];
+        $rules = [];
 
+        if ($this->file('documents') && is_array($this->file('documents'))) {
+            $rules['documents.*'] = $this->file_validation;
+        } elseif ($this->file('documents')) {
+            $rules['documents'] = $this->file_validation;
+        }
+
+        if ($this->file('file') && is_array($this->file('file'))) {
+            $rules['file.*'] = $this->file_validation;
+        } elseif ($this->file('file')) {
+            $rules['file'] = $this->file_validation;
+        }
+
+        $rules['is_public'] = 'sometimes|boolean';
+        
         return $rules;
     }
 
diff --git a/tests/Integration/FileUploadValidationTest.php b/tests/Integration/FileUploadValidationTest.php
new file mode 100644
index 000000000000..68cd436739ec
--- /dev/null
+++ b/tests/Integration/FileUploadValidationTest.php
@@ -0,0 +1,151 @@
+<?php
+/**
+ * Invoice Ninja (https://invoiceninja.com).
+ *
+ * @link https://github.com/invoiceninja/invoiceninja source repository
+ *
+ * @copyright Copyright (c) 2021. Invoice Ninja LLC (https://invoiceninja.com)
+ *
+ * @license https://www.elastic.co/licensing/elastic-license
+ */
+
+namespace Tests\Integration;
+
+use App\Models\Company;
+use App\Utils\Traits\MakesHash;
+use Illuminate\Foundation\Testing\DatabaseTransactions;
+use Illuminate\Http\UploadedFile;
+use Illuminate\Support\Facades\Storage;
+use Tests\MockAccountData;
+use Tests\TestCase;
+
+/**
+ * @test
+ */
+class FileUploadValidationTest extends TestCase
+{
+    use MockAccountData;
+    use DatabaseTransactions;
+    use MakesHash;
+
+    protected function setUp() :void
+    {
+        parent::setUp();
+
+        $this->makeTestData();
+
+    }
+
+    public function testIteratingThroughAllEntities()
+    {
+     
+        Storage::fake('local');
+
+        $file = UploadedFile::fake()->image('avatar.jpg');
+        
+        $data = [
+            'documents' => [$file],
+            'is_public' => false,
+            '_method' => 'PUT',
+        ];
+
+        $entities = [
+            'invoice' => 'invoices',
+            'quote' => 'quotes',
+            'payment' => 'payments',
+            'credit' => 'credits',
+            'expense' => 'expenses',
+            'project' => 'projects',
+            'task' => 'tasks',
+            'vendor' => 'vendors',
+            'product' => 'products',
+            'client' => 'clients',
+            'recurring_invoice' => 'recurring_invoices',
+            'recurring_expense' => 'recurring_expenses',
+        ];
+
+        foreach($entities as $key => $value) {
+
+            $response = $this->withHeaders([
+                'X-API-SECRET' => config('ninja.api_secret'),
+                'X-API-TOKEN' => $this->token,
+            ])->postJson("/api/v1/{$value}/{$this->{$key}->hashed_id}/upload", $data);
+
+            $acc = $response->json();
+            $response->assertStatus(200);
+
+            $this->assertCount(1, $acc['data']['documents']);
+            $this->assertFalse($acc['data']['documents'][0]['is_public']);
+        }
+    
+    }
+
+    public function testFileUploadIsPublicSetsAppropriately()
+    {
+        Storage::fake('local');
+
+        $file = UploadedFile::fake()->image('avatar.jpg');
+        
+        $data = [
+            'documents' => [$file],
+            'is_public' => false,
+            '_method' => 'PUT',
+        ];
+
+        $response = $this->withHeaders([
+            'X-API-SECRET' => config('ninja.api_secret'),
+            'X-API-TOKEN' => $this->token,
+        ])->postJson("/api/v1/invoices/{$this->invoice->hashed_id}/upload", $data);
+
+        $response->assertStatus(200);
+        $acc = $response->json();
+
+        $this->assertCount(1, $acc['data']['documents']);
+        $this->assertFalse($acc['data']['documents'][0]['is_public']);
+
+        $data = [
+                    'documents' => [$file],
+                    'is_public' => true,
+                    '_method' => 'PUT',
+                ];
+
+        $response = $this->withHeaders([
+            'X-API-SECRET' => config('ninja.api_secret'),
+            'X-API-TOKEN' => $this->token,
+        ])->postJson("/api/v1/invoices/{$this->invoice->hashed_id}/upload", $data);
+
+        $response->assertStatus(200);
+        $acc = $response->json();
+
+        $this->assertCount(2, $acc['data']['documents']);
+        $this->assertTrue($acc['data']['documents'][1]['is_public']);
+
+    }
+
+    public function testMultiFileUploadIsPublicSetsAppropriately()
+    {
+        Storage::fake('local');
+
+        $file = UploadedFile::fake()->image('avatar.jpg');
+        
+        $data = [
+            'documents' => [$file, $file],
+            'is_public' => false,
+            '_method' => 'PUT',
+        ];
+
+        $response = $this->withHeaders([
+            'X-API-SECRET' => config('ninja.api_secret'),
+            'X-API-TOKEN' => $this->token,
+        ])->postJson("/api/v1/invoices/{$this->invoice->hashed_id}/upload", $data);
+
+        $response->assertStatus(200);
+        $acc = $response->json();
+
+        $this->assertCount(2, $acc['data']['documents']);
+        $this->assertFalse($acc['data']['documents'][0]['is_public']);
+        $this->assertFalse($acc['data']['documents'][1]['is_public']);
+
+    }
+
+}
\ No newline at end of file
diff --git a/tests/MockAccountData.php b/tests/MockAccountData.php
index 86b039bfcdd3..af4687d7e362 100644
--- a/tests/MockAccountData.php
+++ b/tests/MockAccountData.php
@@ -186,6 +186,10 @@ trait MockAccountData
 
     public $contact;
     
+    public $product;
+
+    public $recurring_invoice;
+
     public function makeTestData()
     {
         config(['database.default' => config('ninja.db.default')]);
@@ -371,6 +375,17 @@ trait MockAccountData
             'client_id' => $this->client->id,
         ]);
 
+        $this->product = Product::factory()->create([
+            'user_id' => $user_id,
+            'company_id' => $this->company->id,
+        ]);
+
+        $this->recurring_invoice = RecurringInvoice::factory()->create([
+            'user_id' => $user_id,
+            'company_id' => $this->company->id,
+            'client_id' => $this->client->id,
+        ]);
+
         $this->expense = Expense::factory()->create([
             'user_id' => $user_id,
             'company_id' => $this->company->id,