diff --git a/visa/visa-server/src/main/java/cn/axzo/nanopart/visa/server/service/impl/ChangeRecordRelationServiceImpl.java b/visa/visa-server/src/main/java/cn/axzo/nanopart/visa/server/service/impl/ChangeRecordRelationServiceImpl.java
index bd1045d6..6804110b 100644
--- a/visa/visa-server/src/main/java/cn/axzo/nanopart/visa/server/service/impl/ChangeRecordRelationServiceImpl.java
+++ b/visa/visa-server/src/main/java/cn/axzo/nanopart/visa/server/service/impl/ChangeRecordRelationServiceImpl.java
@@ -455,6 +455,8 @@ public class ChangeRecordRelationServiceImpl extends ServiceImpl<ChangeRecordRel
         ChangeRecord visa = changeRecordService.getById(req.getVisaId());
         AssertUtil.notNull(visa, "变洽签单据不存在");
 
+        // 移除上一次申请
+        removeLastRequest(visa);
         // 创建电子签合同
         Map<Long, String> essRecipientIdMap = createContract(req, visa);
 
@@ -507,6 +509,13 @@ public class ChangeRecordRelationServiceImpl extends ServiceImpl<ChangeRecordRel
         saveBatch(relations);
     }
 
+    private void removeLastRequest(ChangeRecord visa) {
+        if (!StringUtils.hasText(visa.getContractId())) {
+            return;
+        }
+        deleteByVisaId(visa.getId(), Lists.newArrayList(PRINT_PDF_FILE, PROCESS_INSTANCE_OF_ESS));
+    }
+
     private Map<Long, String> listCooperateShipTypes(VisaRequestStampReq req, ChangeRecord visa) {
         return visaCooperateShipGateway.genericQuery(CooperateShipQueryReq.builder()
                 .workspaceId(visa.getRelationWorkspaceId())