diff --git a/hibernate-envers/src/test/java/org/hibernate/orm/test/envers/StatelessSessionInsertTest.java b/hibernate-envers/src/test/java/org/hibernate/orm/test/envers/StatelessSessionInsertTest.java
new file mode 100644
index 000000000000..06a9b367935b
--- /dev/null
+++ b/hibernate-envers/src/test/java/org/hibernate/orm/test/envers/StatelessSessionInsertTest.java
@@ -0,0 +1,76 @@
+/*
+ * SPDX-License-Identifier: LGPL-2.1-or-later
+ * Copyright Red Hat Inc. and Hibernate Authors
+ */
+package org.hibernate.orm.test.envers;
+
+import org.hibernate.Session;
+import org.hibernate.SessionFactory;
+import org.hibernate.StatelessSession;
+import org.hibernate.envers.Audited;
+
+import org.hibernate.testing.orm.junit.EntityManagerFactoryScope;
+import org.hibernate.testing.orm.junit.Jpa;
+import org.junit.jupiter.api.Test;
+
+import jakarta.persistence.Entity;
+import jakarta.persistence.Id;
+
+@Jpa(annotatedClasses = StatelessSessionInsertTest.ToDo.class)
+public class StatelessSessionInsertTest {
+
+	/**
+	 * Reproduces the NullPointerException in Envers when insert() is called
+	 * on a stateless session.
+	 * <p>
+	 * Because of this error, Envers is not currently compatible with Jakarta Data
+	 * Repositories as the Hibernate metamodel generator generates Jakarta Data Repository
+	 * implementations with stateless sessions.
+	 * <p>
+	 * This test throws a NullPointerException with the message
+	 * "Cannot invoke \"org.hibernate.engine.spi.SessionImplementor.isTransactionInProgress()\"
+	 * because \"session\" is null"
+	 */
+	@Test
+	public void test(EntityManagerFactoryScope scope) {
+		scope.inEntityManager( entityManager -> {
+			Session session = entityManager.unwrap( Session.class );
+			SessionFactory sessionFactory = session.getSessionFactory();
+
+			try (StatelessSession statelessSession = sessionFactory.openStatelessSession()) {
+				ToDo todo = new ToDo();
+				todo.setId( 1L );
+				todo.setTask( "Reproduce the Envers NullPointerException error" );
+
+				// insert() triggers the EnversPostInsertEventListenerImpl event listener,
+				// which tries to call session.isTransactionInProgress() where 'session' is null.
+				statelessSession.insert( todo );
+			}
+		} );
+	}
+
+	@Entity
+	@Audited
+	public static class ToDo {
+		@Id
+		private Long id;
+
+		private String task;
+
+		public Long getId() {
+			return id;
+		}
+
+		public void setId(Long id) {
+			this.id = id;
+		}
+
+		public String getTask() {
+			return task;
+		}
+
+		public void setTask(String task) {
+			this.task = task;
+		}
+	}
+}