diff --git a/modules/document/document.controller.php b/modules/document/document.controller.php
index 0c81d8d4b..e0fdd3008 100644
--- a/modules/document/document.controller.php
+++ b/modules/document/document.controller.php
@@ -1229,7 +1229,7 @@ class DocumentController extends Document
 						// Check for required and strict values.
 						if (!$manual_updated)
 						{
-							$ev_output = $extra_item->validate($value);
+							$ev_output = $extra_item->validate($value, $old_extra_vars[$idx]->value ?? null);
 							if ($ev_output && !$ev_output->toBool())
 							{
 								$oDB->rollback();
@@ -1240,9 +1240,10 @@ class DocumentController extends Document
 						// Handle extra vars that support file upload.
 						if ($extra_item->type === 'file')
 						{
-							// New upload (replace old file)
+							// New upload
 							if (is_array($value) && isset($value['name']))
 							{
+								// Delete old file
 								if (isset($old_extra_vars[$idx]->value))
 								{
 									$fc_output = FileController::getInstance()->deleteFile($old_extra_vars[$idx]->value);
@@ -1252,14 +1253,13 @@ class DocumentController extends Document
 										return $fc_output;
 									}
 								}
-
+								// Insert new file
 								$ev_output = $extra_item->uploadFile($value, $obj->document_srl, 'doc');
 								if (!$ev_output->toBool())
 								{
 									$oDB->rollback();
 									return $ev_output;
 								}
-
 								$value = $ev_output->get('file_srl');
 							}
 							// Delete current file
@@ -1267,6 +1267,14 @@ class DocumentController extends Document
 							{
 								if (isset($old_extra_vars[$idx]->value))
 								{
+									// Check if deletion is allowed
+									$ev_output = $extra_item->validate(null);
+									if (!$ev_output->toBool())
+									{
+										$oDB->rollback();
+										return $ev_output;
+									}
+									// Delete old file
 									$fc_output = FileController::getInstance()->deleteFile($old_extra_vars[$idx]->value);
 									if (!$fc_output->toBool())
 									{
@@ -2674,8 +2682,6 @@ class DocumentController extends Document
 		$js_code[] = 'var validator = xe.getApp("validator")[0];';
 		$js_code[] = 'if(!validator) return false;';
 
-		$logged_info = Context::get('logged_info');
-
 		foreach($extra_keys as $idx => $val)
 		{
 			$idx = $val->idx;
@@ -2683,9 +2689,11 @@ class DocumentController extends Document
 			{
 				$idx .= '[]';
 			}
-			$name = str_ireplace(array('<script', '</script'), array('<scr" + "ipt', '</scr" + "ipt'), $val->name);
-			$js_code[] = sprintf('validator.cast("ADD_MESSAGE", ["extra_vars%s","%s"]);', $idx, $name);
-			if($val->is_required == 'Y') $js_code[] = sprintf('validator.cast("ADD_EXTRA_FIELD", ["extra_vars%s", { required:true }]);', $idx);
+			$js_code[] = sprintf('validator.cast("ADD_MESSAGE", ["extra_vars%s", %s]);', $idx, var_export($val->name, true));
+			if($val->is_required == 'Y' && $val->type !== 'file')
+			{
+				$js_code[] = sprintf('validator.cast("ADD_EXTRA_FIELD", ["extra_vars%s", { required:true }]);', $idx);
+			}
 		}
 
 		$js_code[] = '})(jQuery);';
diff --git a/modules/extravar/models/Value.php b/modules/extravar/models/Value.php
index 22d452e4f..210df0aaf 100644
--- a/modules/extravar/models/Value.php
+++ b/modules/extravar/models/Value.php
@@ -232,9 +232,10 @@ class Value
 	 * Validate a value.
 	 *
 	 * @param mixed $value
+	 * @param mixed $old_value
 	 * @return ?BaseObject
 	 */
-	public function validate($value): ?BaseObject
+	public function validate($value, $old_value = null): ?BaseObject
 	{
 		// Take legacy encoding into consideration.
 		if (is_array($value))
@@ -256,6 +257,11 @@ class Value
 		// Check if a required value is empty.
 		if ($this->is_required === 'Y')
 		{
+			if ($this->type === 'file' && !$value && $old_value)
+			{
+				$value = $old_value;
+				$values = (array)$old_value;
+			}
 			if ($is_array && trim(implode('', $values)) === '')
 			{
 				return new BaseObject(-1, sprintf(lang('common.filter.isnull'), Context::replaceUserLang($this->name)));
diff --git a/modules/extravar/skins/default/form_types/file_upload.blade.php b/modules/extravar/skins/default/form_types/file_upload.blade.php
index 3da47a804..633f97a04 100644
--- a/modules/extravar/skins/default/form_types/file_upload.blade.php
+++ b/modules/extravar/skins/default/form_types/file_upload.blade.php
@@ -17,7 +17,7 @@
 <input type="file" name="{{ $input_name }}"
 	id="{{ $input_id }}"|if="$input_id" class="file rx_ev_file"
 	style="{{ $definition->style }}"|if="$definition->style"
-	@required(toBool($definition->is_required))
+	@required(toBool($definition->is_required) && !$value)
 	@disabled(toBool($definition->is_disabled))
 	@readonly(toBool($definition->is_readonly))
 />