diff --git a/functions.php b/functions.php
index 65b37b42..9f1523d7 100644
--- a/functions.php
+++ b/functions.php
@@ -628,12 +628,14 @@ function checkFileUpload($file, $allowed_extensions) {
 
     // Check a file is actually attached/uploaded
     if ($tmp === '') {
-        return "No file was uploaded.";
+        // No file uploaded
+        return false;
     }
 
     // Check the extension is allowed
     if (!in_array($extension, $allowed_extensions)) {
-        return "File extension not allowed.";
+        // Extension not allowed
+        return false;
     }
 
     // Check the size is under 500 MB
@@ -649,7 +651,7 @@ function checkFileUpload($file, $allowed_extensions) {
     $hashedContent = hash('sha256', $fileContent);
 
     // Generate a secure filename using the hashed content
-    $secureFilename = $hashedContent . '.' . $extension;
+    $secureFilename = $hashedContent . randomString(2) . '.' . $extension;
 
     return $secureFilename;
 }
diff --git a/portal/portal_post.php b/portal/portal_post.php
index 286cd95f..40dac547 100644
--- a/portal/portal_post.php
+++ b/portal/portal_post.php
@@ -77,11 +77,51 @@ if (isset($_POST['add_ticket_comment'])) {
         // Add the comment
         mysqli_query($mysqli, "INSERT INTO ticket_replies SET ticket_reply = '$comment', ticket_reply_type = 'Client', ticket_reply_by = $session_contact_id, ticket_reply_ticket_id = $ticket_id");
 
+        $ticket_reply_id = mysqli_insert_id($mysqli);
+
         // Update Ticket Last Response Field & set ticket to open as client has replied
         mysqli_query($mysqli, "UPDATE tickets SET ticket_status = 'Open' WHERE ticket_id = $ticket_id AND ticket_client_id = $session_client_id LIMIT 1");
 
-        // Redirect
+        // Store any attached any files
+        if (!empty($_FILES)) {
+
+            // Define & create directories, as required
+            mkdirMissing('../uploads/tickets/');
+            $upload_file_dir = "../uploads/tickets/" . $ticket_id . "/";
+            mkdirMissing($upload_file_dir);
+
+            for ($i = 0; $i < count($_FILES['file']['name']); $i++) {
+                // Extract file details for this iteration
+                $single_file = [
+                    'name' => $_FILES['file']['name'][$i],
+                    'type' => $_FILES['file']['type'][$i],
+                    'tmp_name' => $_FILES['file']['tmp_name'][$i],
+                    'error' => $_FILES['file']['error'][$i],
+                    'size' => $_FILES['file']['size'][$i]
+                ];
+
+                if ($ticket_attachment_ref_name = checkFileUpload($single_file, array('jpg', 'jpeg', 'gif', 'png', 'webp', 'pdf', 'txt', 'md', 'doc', 'docx', 'odt', 'csv', 'xls', 'xlsx', 'ods', 'pptx', 'odp', 'zip', 'tar', 'gz', 'xml', 'msg', 'json', 'wav', 'mp3', 'ogg', 'mov', 'mp4', 'av1', 'ovpn'))) {
+
+                    $file_tmp_path = $_FILES['file']['tmp_name'][$i];
+
+                    $file_name = sanitizeInput($_FILES['file']['name'][$i]);
+                    $extarr = explode('.', $_FILES['file']['name'][$i]);
+                    $file_extension = sanitizeInput(strtolower(end($extarr)));
+
+                    // Define destination file path
+                    $dest_path = $upload_file_dir . $ticket_attachment_ref_name;
+
+                    move_uploaded_file($file_tmp_path, $dest_path);
+
+                    mysqli_query($mysqli, "INSERT INTO ticket_attachments SET ticket_attachment_name = '$file_name', ticket_attachment_reference_name = '$ticket_attachment_ref_name', ticket_attachment_reply_id = $ticket_reply_id, ticket_attachment_ticket_id = $ticket_id");
+                }
+
+            }
+        }
+
+        // Redirect back to original page
         header("Location: " . $_SERVER["HTTP_REFERER"]);
+
     } else {
         // The client does not have access to this ticket
         header("Location: portal_post.php?logout");
diff --git a/portal/ticket.php b/portal/ticket.php
index bfc9fa40..4a9ad053 100644
--- a/portal/ticket.php
+++ b/portal/ticket.php
@@ -6,7 +6,6 @@
 
 require_once "inc_portal.php";
 
-
 //Initialize the HTML Purifier to prevent XSS
 require "../plugins/htmlpurifier/HTMLPurifier.standalone.php";
 
@@ -14,6 +13,8 @@ $purifier_config = HTMLPurifier_Config::createDefault();
 $purifier_config->set('URI.AllowedSchemes', ['data' => true, 'src' => true, 'http' => true, 'https' => true]);
 $purifier = new HTMLPurifier($purifier_config);
 
+$allowed_extensions = array('jpg', 'jpeg', 'gif', 'png', 'webp', 'pdf', 'txt', 'md', 'doc', 'docx', 'csv', 'xls', 'xlsx', 'xlsm', 'zip', 'tar', 'gz');
+
 if (isset($_GET['id']) && intval($_GET['id'])) {
     $ticket_id = intval($_GET['id']);
 
@@ -75,11 +76,14 @@ if (isset($_GET['id']) && intval($_GET['id'])) {
 
         <?php if ($ticket_status !== "Closed") { ?>
 
-            <form action="portal_post.php" method="post">
+            <form action="portal_post.php" enctype="multipart/form-data" method="post">
                 <input type="hidden" name="ticket_id" value="<?php echo $ticket_id ?>">
                 <div class="form-group">
                     <textarea class="form-control tinymce" name="comment" placeholder="Add comments.."></textarea>
                 </div>
+                <div class="form-group">
+                    <input type="file" class="form-control-file" name="file[]" multiple id="fileInput" accept=".jpg, .jpeg, .gif, .png, .webp, .pdf, .txt, .md, .doc, .docx, .odt, .csv, .xls, .xlsx, .ods, .pptx, .odp, .zip, .tar, .gz, .xml, .msg, .json, .wav, .mp3, .ogg, .mov, .mp4, .av1, .ovpn">
+                </div>
                 <button type="submit" class="btn btn-primary" name="add_ticket_comment">Reply</button>
             </form>