diff --git a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationAmendmentRequestDao.java b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationAmendmentRequestDao.java
index bead6d7a..df073dd9 100644
--- a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationAmendmentRequestDao.java
+++ b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationAmendmentRequestDao.java
@@ -558,7 +558,7 @@ public class ApplicationAmendmentRequestDao {
 
                     // Add valid new document IDs from the request
                     existingDocumentIds.addAll(validDocumentIds);
-                    applicationDao.updateDocumentDeletionStatus(formEntity, updatedFormField, formEntity.getApplicationForm().getForm(), null,validDocumentIds);
+                    applicationDao.updateDocumentDeletionStatus(formEntity, updatedFormField, formEntity.getApplicationForm().getForm(), null,validDocumentIds,true);
                     // Set the combined document IDs back as the field value
                     formEntity.setFieldValue(String.join(",", existingDocumentIds));
                     applicationFormFieldRepository.save(formEntity);
diff --git a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationDao.java b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationDao.java
index 1f573195..19adbb3c 100644
--- a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationDao.java
+++ b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationDao.java
@@ -427,16 +427,17 @@ public class ApplicationDao {
         Utils.setIfUpdated(applicationFormFieldEntity::getFieldId, applicationFormFieldEntity::setFieldId, applicationFormFieldRequestBean.getFieldId());
 
         if(applicationFormFieldRequestBean.getFieldValue() !=null ) {
-            updateDocumentDeletionStatus(applicationFormFieldEntity, applicationFormFieldRequestBean,formEntity,newDocumentIds,null);
+            updateDocumentDeletionStatus(applicationFormFieldEntity, applicationFormFieldRequestBean,formEntity,newDocumentIds,null,false);
             applicationFormFieldEntity.setFieldValue(Utils.convertObjectToJsonString(applicationFormFieldRequestBean.getFieldValue()));
         }
         if(applicationFormFieldRequestBean.getFieldValue() ==null ) {
+            updateDocumentDeletionStatus(applicationFormFieldEntity, applicationFormFieldRequestBean,formEntity,newDocumentIds,null,false);
             applicationFormFieldEntity.setFieldValue(null);
         }
         return applicationFormFieldRepository.save(applicationFormFieldEntity);
     }
     void updateDocumentDeletionStatus(ApplicationFormFieldEntity applicationFormFieldEntity, ApplicationFormFieldRequestBean applicationFormFieldRequestBean, FormEntity formEntity, List<Long> newDocumentIds,
-                                      List<String> preInstructorDocumentId) {
+                                      List<String> preInstructorDocumentId,boolean isPreInstructor) {
         if (newDocumentIds == null) {
             newDocumentIds = Collections.emptyList();
         }
@@ -450,17 +451,22 @@ public class ApplicationDao {
                 return;
             }
         }
-
+        if(!isPreInstructor){
         List<Long> currentDocumentIds = parseDocumentIds(applicationFormFieldEntity.getFieldValue());
-        if (Boolean.FALSE.equals(newDocumentIds.isEmpty())) {
+        if (Boolean.TRUE.equals(newDocumentIds.isEmpty()))  {
+            currentDocumentIds.forEach(docId -> documentService.deleteFile(docId));
+        } else {
             List<Long> finalNewDocumentIds = newDocumentIds;
             List<Long> documentsToDelete = currentDocumentIds.stream()
                     .filter(docId -> !finalNewDocumentIds.contains(docId))
                     .toList();
             documentsToDelete.forEach(docId -> documentService.deleteFile(docId));
-        }
-
-        if (Boolean.FALSE.equals(preInstructorDocumentId.isEmpty())){
+        }}
+        else{
+            List<Long> currentDocumentIds = parseDocumentIds(applicationFormFieldEntity.getFieldValue());
+        if (Boolean.TRUE.equals(preInstructorDocumentId.isEmpty())) {
+            currentDocumentIds.forEach(docId -> documentService.deleteFile(docId));
+        } else {
             List<Long> preInstructorDocIds = preInstructorDocumentId.stream()
                     .map(Long::valueOf)
                     .collect(Collectors.toList());
@@ -469,7 +475,7 @@ public class ApplicationDao {
                     .filter(docId -> !preInstructorDocIds.contains(docId))
                     .toList();
             documentsToDelete.forEach(docId -> documentService.deleteFile(docId));
-        }
+        }}
     }