diff --git a/src/Playwright.Tests/Assertions/LocatorAssertionsTests.cs b/src/Playwright.Tests/Assertions/LocatorAssertionsTests.cs
index b84b58df6..ba8ea099c 100644
--- a/src/Playwright.Tests/Assertions/LocatorAssertionsTests.cs
+++ b/src/Playwright.Tests/Assertions/LocatorAssertionsTests.cs
@@ -635,6 +635,25 @@ public async Task ShouldSupportToHaveJSProperty()
         await Expect(locator).ToHaveJSPropertyAsync("itsNull", null);
     }
 
+    [PlaywrightTest("playwright-test/playwright.expect.misc.spec.ts", "toHaveJSProperty pass undefined")]
+    public async Task ShouldSupportToHaveJSPropertyUndefined()
+    {
+        await Page.SetContentAsync("<div></div>");
+        var locator = Page.Locator("div");
+        await Expect(locator).ToHaveJSPropertyAsync("foo", JSUndefined.Value);
+
+        await Page.EvalOnSelectorAsync("div", "e => e.foo = null");
+        await Expect(locator).ToHaveJSPropertyAsync("foo", null);
+        var undefinedWhenNull = await PlaywrightAssert.ThrowsAsync<PlaywrightException>(
+            () => Expect(locator).ToHaveJSPropertyAsync("foo", JSUndefined.Value, new() { Timeout = 200 }));
+        StringAssert.Contains("undefined", undefinedWhenNull.Message);
+
+        await Page.EvalOnSelectorAsync("div", "e => { delete e.foo; }");
+        var nullWhenUndefined = await PlaywrightAssert.ThrowsAsync<PlaywrightException>(
+            () => Expect(locator).ToHaveJSPropertyAsync("foo", null, new() { Timeout = 200 }));
+        StringAssert.Contains("unexpected value \"undefined\"", nullWhenUndefined.Message);
+    }
+
     [PlaywrightTest("playwright-test/playwright.expect.misc.spec.ts", "should support toHaveValue")]
     public async Task ShouldSupportToHaveValue()
     {
diff --git a/src/Playwright/API/Types/JSUndefined.cs b/src/Playwright/API/Types/JSUndefined.cs
new file mode 100644
index 000000000..3e5632e15
--- /dev/null
+++ b/src/Playwright/API/Types/JSUndefined.cs
@@ -0,0 +1,54 @@
+/*
+ * MIT License
+ *
+ * Copyright (c) Microsoft Corporation.
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy
+ * of this software and associated documentation files (the "Software"), to deal
+ * in the Software without restriction, including without limitation the rights
+ * to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+ * copies of the Software, and to permit persons to whom the Software is
+ * furnished to do so, subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+ * FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+ * AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+ * LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+ * OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+ * SOFTWARE.
+ */
+
+namespace Microsoft.Playwright;
+
+/// <summary>
+/// Sentinel representing the JavaScript <c>undefined</c> value.
+/// </summary>
+/// <remarks>
+/// <para>
+/// Use this as the expected value of <see cref="ILocatorAssertions.ToHaveJSPropertyAsync"/>
+/// to assert that a JavaScript property is <c>undefined</c> rather than <c>null</c>.
+/// C# <see langword="null"/> continues to mean JavaScript <c>null</c>.
+/// </para>
+/// <para>
+/// This sentinel is only supported by <see cref="ILocatorAssertions.ToHaveJSPropertyAsync"/>.
+/// Passing it to evaluate APIs does not produce JavaScript <c>undefined</c>.
+/// </para>
+/// </remarks>
+public sealed class JSUndefined
+{
+    private JSUndefined()
+    {
+    }
+
+    /// <summary>
+    /// The JavaScript <c>undefined</c> value.
+    /// </summary>
+    public static JSUndefined Value { get; } = new();
+
+    /// <inheritdoc />
+    public override string ToString() => "undefined";
+}
diff --git a/src/Playwright/Core/LocatorAssertions.cs b/src/Playwright/Core/LocatorAssertions.cs
index f1aa62c0c..78aa84a9e 100644
--- a/src/Playwright/Core/LocatorAssertions.cs
+++ b/src/Playwright/Core/LocatorAssertions.cs
@@ -196,7 +196,9 @@ public Task ToHaveJSPropertyAsync(string name, object value, LocatorAssertionsTo
     {
         var commonOptions = ConvertToFrameExpectOptions(options);
         commonOptions.ExpressionArg = name;
-        commonOptions.ExpectedValue = ScriptsHelper.SerializedArgument(value);
+        commonOptions.ExpectedValue = value is JSUndefined
+            ? ScriptsHelper.SerializedUndefinedArgument()
+            : ScriptsHelper.SerializedArgument(value);
         return ExpectImplAsync("to.have.property", null as ExpectedTextValue[], value, $"Locator expected to have JavaScript property '{name}'", "Expect \"ToHaveJSPropertyAsync\"", commonOptions);
     }
 
diff --git a/src/Playwright/Core/ScriptsHelper.cs b/src/Playwright/Core/ScriptsHelper.cs
index 36ca9a2dd..d7ede7074 100644
--- a/src/Playwright/Core/ScriptsHelper.cs
+++ b/src/Playwright/Core/ScriptsHelper.cs
@@ -74,6 +74,9 @@ internal static object SerializedArgument(object? arg)
         return new { value = EvaluateArgumentValueConverter.Serialize(arg, handles, new()), handles };
     }
 
+    internal static object SerializedUndefinedArgument()
+        => new { value = new { v = "undefined" }, handles = new List<EvaluateArgumentGuidElement>() };
+
     internal static string EvaluationScript(string? content, string? path, bool addSourceUrl)
     {
         if (!content.IsNullOrEmpty())