Okay so Milo was on track to what the answer was. and I needed to brush up on muliple file uploads… anyway the solution for me to at least get it to upload… was this
$daFile = $_FILES['files'];
foreach ($_FILES['files'] as $key => $value) {
$daFile[$key] = $value[0];
}
$upload = wp_handle_upload($daFile , array('test_form' => FALSE));
this worked for me and retuned the uploaded file.
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