diff --git a/ebean-test/src/test/java/org/tests/o2m/TestOneToManyStatelessUpdateResultsInSoftDelete.java b/ebean-test/src/test/java/org/tests/o2m/TestOneToManyStatelessUpdateResultsInSoftDelete.java
index e6e86e5dd..d322ad3d3 100644
--- a/ebean-test/src/test/java/org/tests/o2m/TestOneToManyStatelessUpdateResultsInSoftDelete.java
+++ b/ebean-test/src/test/java/org/tests/o2m/TestOneToManyStatelessUpdateResultsInSoftDelete.java
@@ -5,12 +5,10 @@ import io.ebean.DB;
 import io.ebean.test.LoggedSql;
 import io.ebean.xtest.BaseTestCase;
 import org.junit.jupiter.api.Test;
-import org.tests.o2m.dm.GoodsEntity;
-import org.tests.o2m.dm.PersonEntity;
-import org.tests.o2m.dm.WorkflowEntity;
-import org.tests.o2m.dm.WorkflowOperationEntity;
+import org.tests.o2m.dm.*;
 
 import java.io.StringWriter;
+import java.sql.SQLException;
 import java.util.List;
 
 import static org.assertj.core.api.Assertions.assertThat;
@@ -235,4 +233,41 @@ class TestOneToManyStatelessUpdateResultsInSoftDelete extends BaseTestCase {
       assertThat(readGoods.getWorkflowEntity().getOperations()).hasSize(0);
     }
   }
+
+  @Test
+  void setArrayListDoInsertInsteadUpdate() {
+    var attachment1 = new Attachment();
+    attachment1.setName("File1");
+    var attachment2 = new Attachment();
+    attachment1.setName("File2");
+    var goods = new GoodsEntity();
+    goods.setName("goods1");
+    goods.setAttachments(List.of(attachment1, attachment2));
+
+    DB.save(goods);
+
+    var marshaledGoods = DB.json().toBean(GoodsEntity.class, DB.json().toJson(goods));
+    var persistedGoods = DB.find(GoodsEntity.class, goods.getId());
+
+    // this forces insert and throws exception due primary key conflict
+    persistedGoods.setAttachments(marshaledGoods.getAttachments());
+    try {
+      logger.info("Saving goods with set new attachments list");
+      DB.save(persistedGoods);
+    } catch (Exception e) {
+      logger.error("Insert instead update", e);
+    }
+
+    persistedGoods = DB.find(GoodsEntity.class, goods.getId());
+
+    // this works good
+    persistedGoods.getAttachments().clear();
+    persistedGoods.getAttachments().addAll(marshaledGoods.getAttachments());
+    try {
+      logger.info("Saving goods with clear/added attachments");
+        DB.save(persistedGoods);
+    } catch (Exception e) {
+      logger.error("Insert instead update", e);
+    }
+  }
 }
diff --git a/ebean-test/src/test/java/org/tests/o2m/dm/Attachment.java b/ebean-test/src/test/java/org/tests/o2m/dm/Attachment.java
new file mode 100644
index 000000000..411695428
--- /dev/null
+++ b/ebean-test/src/test/java/org/tests/o2m/dm/Attachment.java
@@ -0,0 +1,16 @@
+package org.tests.o2m.dm;
+
+import javax.persistence.Entity;
+
+@Entity
+public class Attachment extends HistoryColumns {
+  private String name;
+
+  public String getName() {
+    return name;
+  }
+
+  public void setName(String name) {
+    this.name = name;
+  }
+}
diff --git a/ebean-test/src/test/java/org/tests/o2m/dm/GoodsEntity.java b/ebean-test/src/test/java/org/tests/o2m/dm/GoodsEntity.java
index ab29d5435..28482c805 100644
--- a/ebean-test/src/test/java/org/tests/o2m/dm/GoodsEntity.java
+++ b/ebean-test/src/test/java/org/tests/o2m/dm/GoodsEntity.java
@@ -1,8 +1,7 @@
 package org.tests.o2m.dm;
 
-import javax.persistence.CascadeType;
-import javax.persistence.Entity;
-import javax.persistence.OneToOne;
+import javax.persistence.*;
+import java.util.List;
 
 @Entity
 public class GoodsEntity extends HistoryColumns {
@@ -11,6 +10,9 @@ public class GoodsEntity extends HistoryColumns {
   @OneToOne(cascade = CascadeType.ALL, orphanRemoval = true)
   private WorkflowEntity workflowEntity;
 
+  @OneToMany(cascade = CascadeType.ALL, orphanRemoval = true)
+  private List<Attachment> attachments;
+
   public String getName() {
     return name;
   }
@@ -26,4 +28,12 @@ public class GoodsEntity extends HistoryColumns {
   public void setWorkflowEntity(WorkflowEntity workflowEntity) {
     this.workflowEntity = workflowEntity;
   }
+
+  public List<Attachment> getAttachments() {
+    return attachments;
+  }
+
+  public void setAttachments(List<Attachment> attachments) {
+    this.attachments = attachments;
+  }
 }