diff --git a/src/test/java/org/tests/transaction/TestTransactionalWhenThrow.java b/src/test/java/org/tests/transaction/TestTransactionalWhenThrow.java
new file mode 100644
index 000000000..057f76ada
--- /dev/null
+++ b/src/test/java/org/tests/transaction/TestTransactionalWhenThrow.java
@@ -0,0 +1,86 @@
+package org.tests.transaction;
+
+import io.ebean.DB;
+import io.ebean.annotation.Transactional;
+import org.junit.Test;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+import org.tests.model.basic.EBasicVer;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatCode;
+
+public class TestTransactionalWhenThrow {
+
+  private static final Logger log = LoggerFactory.getLogger(TestTransactionalWhenThrow.class);
+
+  @Test
+  public void test() {
+    EBasicVer bean = new EBasicVer("doTransactional");
+
+    assertThatCode(() -> doTransactional(bean))
+      .isInstanceOf(IllegalStateException.class)
+      .hasMessageContaining("InnerFailWithSomething");
+
+    final EBasicVer found = DB.find(EBasicVer.class, bean.getId());
+    assertThat(found).isNull();
+  }
+
+  @Transactional
+  private void doTransactional(EBasicVer bean) {
+    DB.save(bean);
+    failWithSomething();
+  }
+
+  private void failWithSomething() {
+    EBasicVer bean = new EBasicVer("failWithSomething");
+    DB.save(bean);
+    throw new IllegalStateException("InnerFailWithSomething");
+  }
+
+  @Test
+  public void testDepth3FailWithCatch() {
+
+    EBasicVer outer = new EBasicVer("testDepth3FailWithCatch");
+
+    assertThatCode(() -> doOuterTransactional(outer))
+      .isInstanceOf(IllegalStateException.class)
+      .hasMessageContaining("Transaction is Inactive");
+
+    final EBasicVer found = DB.find(EBasicVer.class, outer.getId());
+    assertThat(found).isNull();
+  }
+
+  @Transactional
+  void doOuterTransactional(EBasicVer outer) {
+    DB.save(outer);
+    doInnerTransactionWithCatch();
+    // exiting this throws IllegalStateException("Transaction is Inactive")
+    // as doInnerTransactionWithCatch() has caught and not thrown
+  }
+
+  @Transactional
+  private void doInnerTransactionWithCatch() {
+    try {
+      EBasicVer bean = new EBasicVer("doInnerTransactionWithCatch");
+      DB.save(bean);
+      doInnerInner();
+    } catch (Throwable e) {
+      // at this point doInnerInner() has rolled back transaction and marked as inactive
+      log.error("Catch internal error (and not thrown) so caller is unaware", e);
+      // catching and not throwing here means the calling @Transactional method
+      // doOuterTransactional() isn't aware that the transaction has been
+      // rolled back already. It will then exit with:
+      // IllegalStateException("Transaction is Inactive");
+    }
+  }
+
+  @Transactional
+  void doInnerInner() {
+    EBasicVer bean = new EBasicVer("doInnerInner");
+    DB.save(bean);
+    failWithSomething();
+    // exiting this method rolls back transaction
+  }
+
+}