diff --git a/ebean-core/src/main/java/io/ebeaninternal/server/deploy/BeanDescriptor.java b/ebean-core/src/main/java/io/ebeaninternal/server/deploy/BeanDescriptor.java
index 0635d5e06..d50f67423 100644
--- a/ebean-core/src/main/java/io/ebeaninternal/server/deploy/BeanDescriptor.java
+++ b/ebean-core/src/main/java/io/ebeaninternal/server/deploy/BeanDescriptor.java
@@ -2875,8 +2875,8 @@ public class BeanDescriptor<T> implements BeanType<T>, STreeType, SpiBeanType {
     final EntityBeanIntercept ebi = bean._ebean_getIntercept();
     for (BeanPropertyAssocMany<?> many : propertiesManySave) {
       if (ebi.isLoadedProperty(many.propertyIndex())) {
-        final BeanCollection<?> value = (BeanCollection<?>) many.getValue(bean);
-        if (value != null && value.hasModifications()) {
+        final Object value = many.getValue(bean);
+        if (value instanceof BeanCollection && ((BeanCollection<?>)value).hasModifications() || value != null) {
           return true;
         }
       }
diff --git a/ebean-test/src/test/java/org/tests/transparentpersist/TestTransparentPersist.java b/ebean-test/src/test/java/org/tests/transparentpersist/TestTransparentPersist.java
index ed0cfb175..60db7b27b 100644
--- a/ebean-test/src/test/java/org/tests/transparentpersist/TestTransparentPersist.java
+++ b/ebean-test/src/test/java/org/tests/transparentpersist/TestTransparentPersist.java
@@ -13,6 +13,7 @@ import org.tests.model.basic.EBasicVer;
 import org.tests.model.basic.Order;
 import org.tests.model.basic.OrderShipment;
 
+import java.util.ArrayList;
 import java.util.List;
 
 import static org.assertj.core.api.Assertions.assertThat;
@@ -176,6 +177,38 @@ public class TestTransparentPersist extends BaseTestCase {
     DB.delete(Customer.class, c0.getId());
   }
 
+  @Test
+  public void insertWithPersistCascadeInsert() {
+
+    // setup data
+    Customer c0 = new Customer();
+    c0.setName("firstCust");
+    DB.save(c0);
+
+    Integer orderId;
+    try (Transaction transaction = DB.beginTransaction()) {
+      transaction.setAutoPersistUpdates(true); // EXPERIMENTAL feature
+      Order order = new Order();
+      order.setStatus(Order.Status.NEW);
+      order.setCustomer(c0);
+      order.setShipments(new ArrayList<>());
+      DB.insert(order);
+      orderId = order.getId();
+      // cascade persist will insert this Shipment (even though it isn't in the persistence context)
+      OrderShipment osh0 = new OrderShipment();
+      order.addShipment(osh0);
+      transaction.commit();
+    }
+
+    Order checkOrder = DB.find(Order.class, orderId);
+
+    assertThat(checkOrder.getStatus()).isEqualTo(Order.Status.NEW);
+    assertThat(checkOrder.getShipments().size()).isEqualTo(1);
+
+    DB.delete(checkOrder);
+    DB.delete(Customer.class, c0.getId());
+  }
+
   @Test
   public void updateReferenceOnlyWithPersistCascade_Insert_andUpdateForeignKey() {
 
diff --git a/tests/pom.xml b/tests/pom.xml
index 2c79d71fa..28e238922 100644
--- a/tests/pom.xml
+++ b/tests/pom.xml
@@ -17,7 +17,7 @@
 
   <modules>
     <module>test-java16</module>
+    <module>test-kotlin</module>
   </modules>
 
 </project>
-
diff --git a/tests/test-kotlin/pom.xml b/tests/test-kotlin/pom.xml
new file mode 100644
index 000000000..87ef28f4a
--- /dev/null
+++ b/tests/test-kotlin/pom.xml
@@ -0,0 +1,119 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<project xmlns="http://maven.apache.org/POM/4.0.0"
+         xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance"
+         xsi:schemaLocation="http://maven.apache.org/POM/4.0.0 http://maven.apache.org/xsd/maven-4.0.0.xsd">
+  <modelVersion>4.0.0</modelVersion>
+  <parent>
+    <groupId>org.avaje</groupId>
+    <artifactId>java11-oss</artifactId>
+    <version>2.3</version>
+  </parent>
+
+  <name>kotlin test</name>
+  <description>Kotlin specific tests</description>
+  <artifactId>test-kotlin</artifactId>
+  <version>1.0</version>
+
+  <properties>
+    <maven.compiler.source>11</maven.compiler.source>
+    <maven.compiler.target>11</maven.compiler.target>
+
+    <ebean-maven-plugin.version>12.11.5</ebean-maven-plugin.version>
+    <kotlin.version>1.5.31</kotlin.version>
+    <jackson.version>2.12.1</jackson.version>
+  </properties>
+
+  <dependencies>
+    <dependency>
+      <groupId>io.avaje</groupId>
+      <artifactId>junit</artifactId>
+      <version>1.0</version>
+      <scope>test</scope>
+    </dependency>
+
+    <dependency>
+      <groupId>io.ebean</groupId>
+      <artifactId>ebean-test</artifactId>
+      <version>12.11.6-SNAPSHOT</version>
+      <scope>test</scope>
+    </dependency>
+
+    <dependency>
+      <groupId>io.ebean</groupId>
+      <artifactId>ebean-core</artifactId>
+      <version>12.11.6-SNAPSHOT</version>
+      <scope>test</scope>
+    </dependency>
+
+    <dependency>
+      <groupId>ch.qos.logback</groupId>
+      <artifactId>logback-classic</artifactId>
+      <version>1.2.3</version>
+      <scope>test</scope>
+    </dependency>
+
+    <dependency>
+      <groupId>org.jetbrains.kotlin</groupId>
+      <artifactId>kotlin-stdlib-jdk8</artifactId>
+      <version>${kotlin.version}</version>
+      <scope>test</scope>
+    </dependency>
+
+    <dependency>
+      <groupId>org.jetbrains.kotlin</groupId>
+      <artifactId>kotlin-test</artifactId>
+      <version>${kotlin.version}</version>
+      <scope>test</scope>
+    </dependency>
+  </dependencies>
+
+  <build>
+    <testSourceDirectory>src/test/kotlin</testSourceDirectory>
+    <plugins>
+      <plugin>
+        <groupId>org.jetbrains.kotlin</groupId>
+        <artifactId>kotlin-maven-plugin</artifactId>
+        <version>${kotlin.version}</version>
+        <configuration>
+          <jvmTarget>11</jvmTarget>
+        </configuration>
+        <executions>
+          <execution>
+            <id>test-compile</id>
+            <goals>
+              <goal>test-compile</goal>
+            </goals>
+          </execution>
+        </executions>
+      </plugin>
+      <plugin>
+        <groupId>io.ebean</groupId>
+        <artifactId>ebean-maven-plugin</artifactId>
+        <version>${ebean-maven-plugin.version}</version>
+        <executions>
+          <execution>
+            <id>test</id>
+            <phase>process-test-classes</phase>
+            <configuration>
+              <transformArgs>debug=1</transformArgs>
+            </configuration>
+            <goals>
+              <goal>testEnhance</goal>
+            </goals>
+          </execution>
+        </executions>
+      </plugin>
+
+      <!--  TODO remove. May be enable signing in release profile?   -->
+      <plugin>
+        <groupId>org.apache.maven.plugins</groupId>
+        <artifactId>maven-gpg-plugin</artifactId>
+        <version>1.6</version>
+        <configuration>
+          <skip>true</skip>
+        </configuration>
+      </plugin>
+    </plugins>
+  </build>
+
+</project>
diff --git a/tests/test-kotlin/src/test/kotlin/io/ebean/test/kotlin/TransparentPersistenceTest.kt b/tests/test-kotlin/src/test/kotlin/io/ebean/test/kotlin/TransparentPersistenceTest.kt
new file mode 100644
index 000000000..06497c458
--- /dev/null
+++ b/tests/test-kotlin/src/test/kotlin/io/ebean/test/kotlin/TransparentPersistenceTest.kt
@@ -0,0 +1,41 @@
+package io.ebean.test.kotlin
+
+import io.ebean.DB
+import org.assertj.core.api.Assertions.assertThat
+import org.example.order.Customer
+import org.example.order.Order
+import org.example.order.OrderItem
+import org.junit.jupiter.api.Test
+import java.math.BigDecimal
+import kotlin.test.assertNotNull
+
+class TransparentPersistenceTest {
+
+  @Test
+  fun `insert with cascade insert`() {
+    // setup data
+
+    // setup data
+    val c0 = Customer("Customer 0")
+    DB.save(c0)
+
+    var orderId: Long
+    DB.beginTransaction().use { transaction ->
+      transaction.setAutoPersistUpdates(true) // EXPERIMENTAL feature
+      val order = Order(c0)
+      DB.insert(order)
+      orderId = order.id
+      // cascade persist will insert this OrderItem (even though it isn't in the persistence context)
+      order.items.add(OrderItem(order, "item 0", BigDecimal.TEN))
+      transaction.commit()
+    }
+
+    val checkOrder = DB.find(Order::class.java, orderId)
+
+    assertNotNull(checkOrder)
+    assertThat(checkOrder.items.size).isEqualTo(1)
+
+    DB.delete(checkOrder)
+    DB.delete(c0)
+  }
+}
diff --git a/tests/test-kotlin/src/test/kotlin/org/example/order/Customer.kt b/tests/test-kotlin/src/test/kotlin/org/example/order/Customer.kt
new file mode 100644
index 000000000..72c2795af
--- /dev/null
+++ b/tests/test-kotlin/src/test/kotlin/org/example/order/Customer.kt
@@ -0,0 +1,17 @@
+package org.example.order
+
+import javax.persistence.Entity
+import javax.persistence.Id
+import javax.persistence.Version
+
+@Entity
+class Customer(
+  name: String,
+) {
+  @Id
+  var id: Int = 0
+  val name: String = name
+
+  @Version
+  var version: Long = 0
+}
diff --git a/tests/test-kotlin/src/test/kotlin/org/example/order/Order.kt b/tests/test-kotlin/src/test/kotlin/org/example/order/Order.kt
new file mode 100644
index 000000000..a5e87f9d9
--- /dev/null
+++ b/tests/test-kotlin/src/test/kotlin/org/example/order/Order.kt
@@ -0,0 +1,27 @@
+package org.example.order
+
+import javax.persistence.CascadeType
+import javax.persistence.Entity
+import javax.persistence.Id
+import javax.persistence.ManyToOne
+import javax.persistence.OneToMany
+import javax.persistence.Table
+import javax.persistence.Version
+
+@Entity
+@Table(name = "t_order")
+class Order(
+  customer: Customer,
+) {
+  @Id
+  val id: Long = 0
+
+  @ManyToOne
+  val customer: Customer = customer
+
+  @OneToMany(mappedBy = "order", cascade = [CascadeType.ALL], orphanRemoval = true)
+  val items: MutableList<OrderItem> = mutableListOf()
+
+  @Version
+  val version: Long = 0
+}
diff --git a/tests/test-kotlin/src/test/kotlin/org/example/order/OrderItem.kt b/tests/test-kotlin/src/test/kotlin/org/example/order/OrderItem.kt
new file mode 100644
index 000000000..6a7e123ec
--- /dev/null
+++ b/tests/test-kotlin/src/test/kotlin/org/example/order/OrderItem.kt
@@ -0,0 +1,29 @@
+package org.example.order
+
+import java.math.BigDecimal
+import javax.persistence.Entity
+import javax.persistence.Id
+import javax.persistence.ManyToOne
+
+@Entity
+class OrderItem(
+  order: Order,
+  name: String,
+  price: BigDecimal,
+  amount: Int = 1,
+  description: String? = null,
+) {
+  @Id
+  val id: Long = 0
+
+  @ManyToOne
+  val order: Order = order
+
+  val name: String = name
+
+  val description: String? = description
+
+  val amount: Int = amount
+
+  val price: BigDecimal = price
+}
diff --git a/tests/test-kotlin/src/test/resources/application-test.yaml b/tests/test-kotlin/src/test/resources/application-test.yaml
new file mode 100644
index 000000000..029b11023
--- /dev/null
+++ b/tests/test-kotlin/src/test/resources/application-test.yaml
@@ -0,0 +1,6 @@
+ebean:
+  test:
+    platform: h2
+    ddlMode: dropCreate
+    dbName: foo
+
diff --git a/tests/test-kotlin/src/test/resources/logback-test.xml b/tests/test-kotlin/src/test/resources/logback-test.xml
new file mode 100644
index 000000000..ce7ad5968
--- /dev/null
+++ b/tests/test-kotlin/src/test/resources/logback-test.xml
@@ -0,0 +1,22 @@
+<configuration scan="true" scanPeriod="10 seconds">
+  <appender name="STDOUT" class="ch.qos.logback.core.ConsoleAppender">
+    <encoder class="ch.qos.logback.classic.encoder.PatternLayoutEncoder">
+      <pattern>%d{HH:mm:ss.SSS} [%thread] %-5level %logger{36} - %msg%n</pattern>
+    </encoder>
+  </appender>
+
+  <root level="INFO">
+    <appender-ref ref="STDOUT"/>
+  </root>
+
+  <logger name="org.avaje" level="TRACE"/>
+  <logger name="io.ebean" level="INFO"/>
+
+  <logger name="io.ebean.docker" level="TRACE"/>
+  <logger name="io.ebean.DDL" level="DEBUG"/>
+
+  <logger name="io.ebean.SQL" level="TRACE"/>
+  <logger name="io.ebean.TXN" level="TRACE"/>
+  <logger name="io.ebean.SUM" level="TRACE"/>
+
+</configuration>