diff --git a/app/Mail/Engine/CreditEmailEngine.php b/app/Mail/Engine/CreditEmailEngine.php
index feffbcf0181a..2aafed3d1c1e 100644
--- a/app/Mail/Engine/CreditEmailEngine.php
+++ b/app/Mail/Engine/CreditEmailEngine.php
@@ -119,6 +119,10 @@ class CreditEmailEngine extends BaseEmailEngine
 
             $pdf = ((new CreateRawPdf($this->invitation))->handle());
 
+                if($this->client->getSetting('embed_documents') && ($this->credit->documents()->where('is_public', true)->count() > 0 || $this->credit->company->documents()->where('is_public', true)->count() > 0)) {
+                    $pdf = $this->credit->documentMerge($pdf);
+                }
+
             $this->setAttachments([['file' => base64_encode($pdf), 'name' => $this->credit->numberFormatter().'.pdf']]);
         }
 
diff --git a/app/Mail/Engine/InvoiceEmailEngine.php b/app/Mail/Engine/InvoiceEmailEngine.php
index 8f9e15f8dbf0..23bdba41c315 100644
--- a/app/Mail/Engine/InvoiceEmailEngine.php
+++ b/app/Mail/Engine/InvoiceEmailEngine.php
@@ -131,6 +131,10 @@ class InvoiceEmailEngine extends BaseEmailEngine
         if ($this->client->getSetting('pdf_email_attachment') !== false && $this->invoice->company->account->hasFeature(Account::FEATURE_PDF_ATTACHMENT)) {
             $pdf = ((new CreateRawPdf($this->invitation))->handle());
 
+            if($this->client->getSetting('embed_documents') && ($this->invoice->documents()->where('is_public', true)->count() > 0 || $this->invoice->company->documents()->where('is_public', true)->count() > 0)) {
+                $pdf = $this->invoice->documentMerge($pdf);
+            }
+
             $this->setAttachments([['file' => base64_encode($pdf), 'name' => $this->invoice->numberFormatter().'.pdf']]);
         }
 
diff --git a/app/Mail/Engine/PurchaseOrderEmailEngine.php b/app/Mail/Engine/PurchaseOrderEmailEngine.php
index 168544aea23a..cef7173466a3 100644
--- a/app/Mail/Engine/PurchaseOrderEmailEngine.php
+++ b/app/Mail/Engine/PurchaseOrderEmailEngine.php
@@ -123,6 +123,10 @@ class PurchaseOrderEmailEngine extends BaseEmailEngine
 
             $pdf = (new CreateRawPdf($this->invitation))->handle();
 
+            if($this->vendor->getSetting('embed_documents') && ($this->purchase_order->documents()->where('is_public', true)->count() > 0 || $this->purchase_order->company->documents()->where('is_public', true)->count() > 0)) {
+                $pdf = $this->purchase_order->documentMerge($pdf);
+            }
+
             $this->setAttachments([['file' => base64_encode($pdf), 'name' => $this->purchase_order->numberFormatter().'.pdf']]);
         }
 
diff --git a/app/Mail/Engine/QuoteEmailEngine.php b/app/Mail/Engine/QuoteEmailEngine.php
index f0dad52d58bf..d43592595080 100644
--- a/app/Mail/Engine/QuoteEmailEngine.php
+++ b/app/Mail/Engine/QuoteEmailEngine.php
@@ -17,6 +17,7 @@ use App\Models\Account;
 use App\Utils\HtmlEngine;
 use Illuminate\Support\Str;
 use App\Jobs\Entity\CreateRawPdf;
+use App\Services\PdfMaker\PdfMerge;
 use Illuminate\Support\Facades\App;
 use Illuminate\Support\Facades\URL;
 use Illuminate\Support\Facades\Cache;
@@ -117,6 +118,10 @@ class QuoteEmailEngine extends BaseEmailEngine
         if ($this->client->getSetting('pdf_email_attachment') !== false && $this->quote->company->account->hasFeature(Account::FEATURE_PDF_ATTACHMENT)) {
             $pdf = ((new CreateRawPdf($this->invitation))->handle());
 
+                if($this->client->getSetting('embed_documents') && ($this->quote->documents()->where('is_public', true)->count() > 0 || $this->quote->company->documents()->where('is_public', true)->count() > 0)){
+                    $pdf = $this->quote->documentMerge($pdf);
+                }
+
             $this->setAttachments([['file' => base64_encode($pdf), 'name' => $this->quote->numberFormatter().'.pdf']]);
         }
 
diff --git a/app/Models/BaseModel.php b/app/Models/BaseModel.php
index 2e6e81066729..19b443c476db 100644
--- a/app/Models/BaseModel.php
+++ b/app/Models/BaseModel.php
@@ -11,16 +11,17 @@
 
 namespace App\Models;
 
+use Illuminate\Support\Str;
+use Illuminate\Support\Carbon;
+use App\Utils\Traits\MakesHash;
 use App\Jobs\Entity\CreateRawPdf;
 use App\Jobs\Util\WebhookHandler;
 use App\Models\Traits\Excludable;
-use App\Utils\Traits\MakesHash;
+use App\Services\PdfMaker\PdfMerge;
+use Illuminate\Database\Eloquent\Model;
 use App\Utils\Traits\UserSessionAttributes;
 use Illuminate\Database\Eloquent\Factories\HasFactory;
-use Illuminate\Database\Eloquent\Model;
 use Illuminate\Database\Eloquent\ModelNotFoundException as ModelNotFoundException;
-use Illuminate\Support\Carbon;
-use Illuminate\Support\Str;
 
 /**
  * Class BaseModel
@@ -77,6 +78,8 @@ class BaseModel extends Model
     use UserSessionAttributes;
     use HasFactory;
     use Excludable;
+    
+    public int $max_attachment_size = 3000000;
 
     protected $appends = [
         'hashed_id',
@@ -337,4 +340,42 @@ class BaseModel extends Model
         return strtr($section, $variables['values']);
 
     }
+    
+    /**
+     * Merged PDFs associated with the entity / company
+     * into a single document
+     *
+     * @param  string $pdf
+     * @return mixed
+     */
+    public function documentMerge(string $pdf): mixed
+    {
+        $files = collect([$pdf]);
+
+        $entity_docs = $this->documents()
+        ->where('is_public', true)
+        ->get()
+        ->filter(function ($document) {
+            return $document->size < $this->max_attachment_size && stripos($document->name, ".pdf") !== false;
+        })->map(function ($d) {
+            return $d->getFile();
+        });
+
+        $files->push($entity_docs);
+
+        $company_docs = $this->company->documents()
+        ->where('is_public', true)
+        ->get()
+        ->filter(function ($document) {
+            return $document->size < $this->max_attachment_size && stripos($document->name, ".pdf") !== false;
+        })->map(function ($d) {
+            return $d->getFile();
+        });
+
+        $files->push($company_docs);
+
+        $pdf = (new PdfMerge($files->flatten()->toArray()))->run();
+
+        return $pdf;
+    }
 }
diff --git a/app/Services/Email/EmailDefaults.php b/app/Services/Email/EmailDefaults.php
index 1053632b4328..79c7dcf812a3 100644
--- a/app/Services/Email/EmailDefaults.php
+++ b/app/Services/Email/EmailDefaults.php
@@ -309,6 +309,11 @@ class EmailDefaults
         /** Purchase Order / Invoice / Credit / Quote PDF  */
         if ($this->email->email_object->settings->pdf_email_attachment) {
             $pdf = ((new CreateRawPdf($this->email->email_object->invitation))->handle());
+
+            if($this->email->email_object->settings->embed_documents && ($this->email->email_object->entity->documents()->where('is_public', true)->count() > 0 || $this->email->email_object->entity->company->documents()->where('is_public', true)->count() > 0)) {
+                $pdf = $this->email->email_object->entity->documentMerge($pdf);
+            }
+
             $this->email->email_object->attachments = array_merge($this->email->email_object->attachments, [['file' => base64_encode($pdf), 'name' => $this->email->email_object->entity->numberFormatter().'.pdf']]);
         }