diff --git a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationAmendmentRequestDao.java b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationAmendmentRequestDao.java
index d685796f..bead6d7a 100644
--- a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationAmendmentRequestDao.java
+++ b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationAmendmentRequestDao.java
@@ -96,6 +96,8 @@ public class ApplicationAmendmentRequestDao {
 
     @Autowired
     private Validator validator;
+    @Autowired
+    private ApplicationDao applicationDao;
 
     public ApplicationAmendmentRequestResponse getApplicationDataForAmendment(Long applicationEvaluationId) {
         log.info("Fetching the application data for the Amendment process {}", applicationEvaluationId);
@@ -556,11 +558,10 @@ public class ApplicationAmendmentRequestDao {
 
                     // Add valid new document IDs from the request
                     existingDocumentIds.addAll(validDocumentIds);
-
+                    applicationDao.updateDocumentDeletionStatus(formEntity, updatedFormField, formEntity.getApplicationForm().getForm(), null,validDocumentIds);
                     // Set the combined document IDs back as the field value
                     formEntity.setFieldValue(String.join(",", existingDocumentIds));
                     applicationFormFieldRepository.save(formEntity);
-
                     log.info("Updated field value for application ID {} and field ID {} with document IDs {}",
                             applicationAmendment.getApplicationId(), updatedFormField.getFieldId(), String.join(",", existingDocumentIds));
                     fieldUpdated = true;
diff --git a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationDao.java b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationDao.java
index cf2e08c2..1f573195 100644
--- a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationDao.java
+++ b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationDao.java
@@ -405,7 +405,7 @@ public class ApplicationDao {
 
         ApplicationFormFieldEntity applicationFormFieldEntity=null;
 
-        validateFileUploadDocuments(applicationFormFieldRequestBean, formEntity);
+        List<Long> newDocumentIds =validateFileUploadDocuments(applicationFormFieldRequestBean, formEntity);
 
         if(applicationFormFieldEntities==null || applicationFormFieldEntities.isEmpty()){
             applicationFormFieldEntity = new ApplicationFormFieldEntity();
@@ -427,13 +427,73 @@ public class ApplicationDao {
         Utils.setIfUpdated(applicationFormFieldEntity::getFieldId, applicationFormFieldEntity::setFieldId, applicationFormFieldRequestBean.getFieldId());
 
         if(applicationFormFieldRequestBean.getFieldValue() !=null ) {
-        applicationFormFieldEntity.setFieldValue(Utils.convertObjectToJsonString(applicationFormFieldRequestBean.getFieldValue()));
-    }
+            updateDocumentDeletionStatus(applicationFormFieldEntity, applicationFormFieldRequestBean,formEntity,newDocumentIds,null);
+            applicationFormFieldEntity.setFieldValue(Utils.convertObjectToJsonString(applicationFormFieldRequestBean.getFieldValue()));
+        }
         if(applicationFormFieldRequestBean.getFieldValue() ==null ) {
             applicationFormFieldEntity.setFieldValue(null);
         }
         return applicationFormFieldRepository.save(applicationFormFieldEntity);
     }
+    void updateDocumentDeletionStatus(ApplicationFormFieldEntity applicationFormFieldEntity, ApplicationFormFieldRequestBean applicationFormFieldRequestBean, FormEntity formEntity, List<Long> newDocumentIds,
+                                      List<String> preInstructorDocumentId) {
+        if (newDocumentIds == null) {
+            newDocumentIds = Collections.emptyList();
+        }
+        if (preInstructorDocumentId == null) {
+            preInstructorDocumentId = Collections.emptyList();
+        }
+
+        List<ContentResponseBean> contentResponseBeans = formDao.convertFormEntityToFormResponseBean(formEntity).getContent();
+        for (ContentResponseBean contentResponseBean : contentResponseBeans) {
+            if (Boolean.FALSE.equals(contentResponseBean.getName().equals("fileupload"))) {
+                return;
+            }
+        }
+
+        List<Long> currentDocumentIds = parseDocumentIds(applicationFormFieldEntity.getFieldValue());
+        if (Boolean.FALSE.equals(newDocumentIds.isEmpty())) {
+            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())){
+            List<Long> preInstructorDocIds = preInstructorDocumentId.stream()
+                    .map(Long::valueOf)
+                    .collect(Collectors.toList());
+
+            List<Long> documentsToDelete = currentDocumentIds.stream()
+                    .filter(docId -> !preInstructorDocIds.contains(docId))
+                    .toList();
+            documentsToDelete.forEach(docId -> documentService.deleteFile(docId));
+        }
+    }
+
+
+    private List<Long> parseDocumentIds(String fieldValue) {
+        if (fieldValue == null || fieldValue.isEmpty()) {
+            return Collections.emptyList();
+        }
+        if (fieldValue.contains(",")) {
+            return Arrays.stream(fieldValue.split(","))
+                    .map(String::trim)
+                    .map(Long::parseLong)
+                    .collect(Collectors.toList());
+        } else {
+            try {
+                return Collections.singletonList(Long.parseLong(fieldValue.trim()));
+            } catch (NumberFormatException e) {
+                e.printStackTrace();
+                return Collections.emptyList();
+            }
+        }
+    }
+
+
+
 
     private List<Long> validateFileUploadDocuments(ApplicationFormFieldRequestBean applicationFormFieldRequestBean, FormEntity formEntity) {
         List<Long> documentIds=null;
diff --git a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationEvaluationDao.java b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationEvaluationDao.java
index 2bcbade9..9ab569b0 100644
--- a/src/main/java/net/gepafin/tendermanagement/dao/ApplicationEvaluationDao.java
+++ b/src/main/java/net/gepafin/tendermanagement/dao/ApplicationEvaluationDao.java
@@ -249,19 +249,21 @@ public class ApplicationEvaluationDao {
             List<DocumentResponseBean> documentResponseBeans = new ArrayList<>();
 
             for (String docId : documentIds) {
-                Long documentId = Long.valueOf(docId.trim());
-                documentRepository.findByIdAndNotDeleted(documentId).ifPresent(documentEntity -> {
-                    DocumentResponseBean responseBean = new DocumentResponseBean();
-                    responseBean.setId(documentEntity.getId());
-                    responseBean.setName(documentEntity.getFileName());
-                    responseBean.setType(DocumentTypeEnum.valueOf(documentEntity.getType()));
-                    responseBean.setSource(DocumentSourceTypeEnum.valueOf(documentEntity.getSource()));
-                    responseBean.setSourceId(documentEntity.getSourceId());
-                    responseBean.setFilePath(documentEntity.getFilePath());
-                    responseBean.setCreatedDate(documentEntity.getCreatedDate());
-                    responseBean.setUpdatedDate(documentEntity.getUpdatedDate());
-                    documentResponseBeans.add(responseBean);
-                });
+                if (Boolean.FALSE.equals(docId.isEmpty())){
+                    Long documentId = Long.valueOf(docId.trim());
+                    documentRepository.findByIdAndNotDeleted(documentId).ifPresent(documentEntity -> {
+                        DocumentResponseBean responseBean = new DocumentResponseBean();
+                        responseBean.setId(documentEntity.getId());
+                        responseBean.setName(documentEntity.getFileName());
+                        responseBean.setType(DocumentTypeEnum.valueOf(documentEntity.getType()));
+                        responseBean.setSource(DocumentSourceTypeEnum.valueOf(documentEntity.getSource()));
+                        responseBean.setSourceId(documentEntity.getSourceId());
+                        responseBean.setFilePath(documentEntity.getFilePath());
+                        responseBean.setCreatedDate(documentEntity.getCreatedDate());
+                        responseBean.setUpdatedDate(documentEntity.getUpdatedDate());
+                        documentResponseBeans.add(responseBean);
+                    });
+                }
             }
             mappedField.setFieldValue(documentResponseBeans);
         }
@@ -351,19 +353,21 @@ public class ApplicationEvaluationDao {
                                     List<DocumentResponseBean> documentResponseBeans = new ArrayList<>();
 
                                     for (String docId : documentIds) {
-                                        Long documentId = Long.valueOf(docId.trim());
-                                        documentRepository.findByIdAndNotDeleted(documentId).ifPresent(documentEntity -> {
-                                            DocumentResponseBean responseBean = new DocumentResponseBean();
-                                            responseBean.setId(documentEntity.getId());
-                                            responseBean.setName(documentEntity.getFileName());
-                                            responseBean.setType(DocumentTypeEnum.valueOf(documentEntity.getType()));
-                                            responseBean.setSource(DocumentSourceTypeEnum.valueOf(documentEntity.getSource()));
-                                            responseBean.setSourceId(documentEntity.getSourceId());
-                                            responseBean.setFilePath(documentEntity.getFilePath());
-                                            responseBean.setCreatedDate(documentEntity.getCreatedDate());
-                                            responseBean.setUpdatedDate(documentEntity.getUpdatedDate());
-                                            documentResponseBeans.add(responseBean);
-                                        });
+                                         if (Boolean.FALSE.equals(docId.isEmpty())){
+                                            Long documentId = Long.valueOf(docId.trim());
+                                            documentRepository.findByIdAndNotDeleted(documentId).ifPresent(documentEntity -> {
+                                                DocumentResponseBean responseBean = new DocumentResponseBean();
+                                                responseBean.setId(documentEntity.getId());
+                                                responseBean.setName(documentEntity.getFileName());
+                                                responseBean.setType(DocumentTypeEnum.valueOf(documentEntity.getType()));
+                                                responseBean.setSource(DocumentSourceTypeEnum.valueOf(documentEntity.getSource()));
+                                                responseBean.setSourceId(documentEntity.getSourceId());
+                                                responseBean.setFilePath(documentEntity.getFilePath());
+                                                responseBean.setCreatedDate(documentEntity.getCreatedDate());
+                                                responseBean.setUpdatedDate(documentEntity.getUpdatedDate());
+                                                documentResponseBeans.add(responseBean);
+                                            });
+                                        }
                                     }
 
                                     fieldResponse.setFileDetail(documentResponseBeans);
@@ -888,19 +892,21 @@ public class ApplicationEvaluationDao {
                                 List<DocumentResponseBean> documentResponseBeans = new ArrayList<>();
 
                                 for (String docId : documentIds) {
-                                    Long documentId = Long.valueOf(docId.trim());
-                                    documentRepository.findByIdAndNotDeleted(documentId).ifPresent(documentEntity -> {
-                                        DocumentResponseBean responseBean = new DocumentResponseBean();
-                                        responseBean.setId(documentEntity.getId());
-                                        responseBean.setName(documentEntity.getFileName());
-                                        responseBean.setType(DocumentTypeEnum.valueOf(documentEntity.getType()));
-                                        responseBean.setSource(DocumentSourceTypeEnum.valueOf(documentEntity.getSource()));
-                                        responseBean.setSourceId(documentEntity.getSourceId());
-                                        responseBean.setFilePath(documentEntity.getFilePath());
-                                        responseBean.setCreatedDate(documentEntity.getCreatedDate());
-                                        responseBean.setUpdatedDate(documentEntity.getUpdatedDate());
-                                        documentResponseBeans.add(responseBean);
-                                    });
+                                    if (Boolean.FALSE.equals(docId.isEmpty())) {
+                                        Long documentId = Long.valueOf(docId.trim());
+                                        documentRepository.findByIdAndNotDeleted(documentId).ifPresent(documentEntity -> {
+                                            DocumentResponseBean responseBean = new DocumentResponseBean();
+                                            responseBean.setId(documentEntity.getId());
+                                            responseBean.setName(documentEntity.getFileName());
+                                            responseBean.setType(DocumentTypeEnum.valueOf(documentEntity.getType()));
+                                            responseBean.setSource(DocumentSourceTypeEnum.valueOf(documentEntity.getSource()));
+                                            responseBean.setSourceId(documentEntity.getSourceId());
+                                            responseBean.setFilePath(documentEntity.getFilePath());
+                                            responseBean.setCreatedDate(documentEntity.getCreatedDate());
+                                            responseBean.setUpdatedDate(documentEntity.getUpdatedDate());
+                                            documentResponseBeans.add(responseBean);
+                                        });
+                                    }
                                 }
 
                                 fieldResponse.setFileDetail(documentResponseBeans);
@@ -1247,21 +1253,22 @@ public class ApplicationEvaluationDao {
                                 List<DocumentResponseBean> documentResponseBeans = new ArrayList<>();
 
                                 for (String docId : documentIds) {
-                                    Long documentId = Long.valueOf(docId.trim());
-                                    documentRepository.findByIdAndNotDeleted(documentId).ifPresent(documentEntity -> {
-                                        DocumentResponseBean responseBean = new DocumentResponseBean();
-                                        responseBean.setId(documentEntity.getId());
-                                        responseBean.setName(documentEntity.getFileName());
-                                        responseBean.setType(DocumentTypeEnum.valueOf(documentEntity.getType()));
-                                        responseBean.setSource(DocumentSourceTypeEnum.valueOf(documentEntity.getSource()));
-                                        responseBean.setSourceId(documentEntity.getSourceId());
-                                        responseBean.setFilePath(documentEntity.getFilePath());
-                                        responseBean.setCreatedDate(documentEntity.getCreatedDate());
-                                        responseBean.setUpdatedDate(documentEntity.getUpdatedDate());
-                                        documentResponseBeans.add(responseBean);
-                                    });
+                                     if (Boolean.FALSE.equals(docId.isEmpty())){
+                                        Long documentId = Long.valueOf(docId.trim());
+                                        documentRepository.findByIdAndNotDeleted(documentId).ifPresent(documentEntity -> {
+                                            DocumentResponseBean responseBean = new DocumentResponseBean();
+                                            responseBean.setId(documentEntity.getId());
+                                            responseBean.setName(documentEntity.getFileName());
+                                            responseBean.setType(DocumentTypeEnum.valueOf(documentEntity.getType()));
+                                            responseBean.setSource(DocumentSourceTypeEnum.valueOf(documentEntity.getSource()));
+                                            responseBean.setSourceId(documentEntity.getSourceId());
+                                            responseBean.setFilePath(documentEntity.getFilePath());
+                                            responseBean.setCreatedDate(documentEntity.getCreatedDate());
+                                            responseBean.setUpdatedDate(documentEntity.getUpdatedDate());
+                                            documentResponseBeans.add(responseBean);
+                                        });
+                                    }
                                 }
-
                                 fieldResponse.setFileDetail(documentResponseBeans);
                                 fieldResponses.add(fieldResponse);
                             }