diff --git a/playwright/src/main/java/com/microsoft/playwright/impl/Serialization.java b/playwright/src/main/java/com/microsoft/playwright/impl/Serialization.java
index 34899dfbb..4aa6e793f 100644
--- a/playwright/src/main/java/com/microsoft/playwright/impl/Serialization.java
+++ b/playwright/src/main/java/com/microsoft/playwright/impl/Serialization.java
@@ -45,6 +45,7 @@ class Serialization {
     .registerTypeAdapter(Date.class, new DateSerializer())
     .registerTypeAdapter(LocalDateTime.class, new LocalDateTimeSerializer())
     .registerTypeAdapter(SameSiteAttribute.class, new SameSiteAdapter().nullSafe())
+    .registerTypeAdapter(AnnotatePosition.class, new ToLowerCaseAndDashSerializer<AnnotatePosition>())
     .registerTypeAdapter(BrowserChannel.class, new ToLowerCaseAndDashSerializer<BrowserChannel>())
     .registerTypeAdapter(ColorScheme.class, new ToLowerCaseAndDashSerializer<ColorScheme>())
     .registerTypeAdapter(Contrast.class, new ToLowerCaseAndDashSerializer<Contrast>())
diff --git a/playwright/src/test/java/com/microsoft/playwright/impl/TestSerialization.java b/playwright/src/test/java/com/microsoft/playwright/impl/TestSerialization.java
new file mode 100644
index 000000000..b8adef4dd
--- /dev/null
+++ b/playwright/src/test/java/com/microsoft/playwright/impl/TestSerialization.java
@@ -0,0 +1,35 @@
+/*
+ * Copyright (c) Microsoft Corporation.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ * http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package com.microsoft.playwright.impl;
+
+import com.microsoft.playwright.options.AnnotatePosition;
+import org.junit.jupiter.api.Test;
+
+import static com.microsoft.playwright.impl.Serialization.gson;
+import static org.junit.jupiter.api.Assertions.assertEquals;
+
+public class TestSerialization {
+  @Test
+  void annotatePositionSerializesToLowerCaseAndDash() {
+    assertEquals("top-left", gson().toJsonTree(AnnotatePosition.TOP_LEFT).getAsString());
+    assertEquals("top", gson().toJsonTree(AnnotatePosition.TOP).getAsString());
+    assertEquals("top-right", gson().toJsonTree(AnnotatePosition.TOP_RIGHT).getAsString());
+    assertEquals("bottom-left", gson().toJsonTree(AnnotatePosition.BOTTOM_LEFT).getAsString());
+    assertEquals("bottom", gson().toJsonTree(AnnotatePosition.BOTTOM).getAsString());
+    assertEquals("bottom-right", gson().toJsonTree(AnnotatePosition.BOTTOM_RIGHT).getAsString());
+  }
+}