diff --git a/src/Playwright.MSTest/PlaywrightTest.cs b/src/Playwright.MSTest/PlaywrightTest.cs
index e60c5cbd8..b0a7f59d7 100644
--- a/src/Playwright.MSTest/PlaywrightTest.cs
+++ b/src/Playwright.MSTest/PlaywrightTest.cs
@@ -53,4 +53,10 @@ public async Task PlaywrightSetup()
     public IPageAssertions Expect(IPage page) => Assertions.Expect(page);
 
     public IAPIResponseAssertions Expect(IAPIResponse response) => Assertions.Expect(response);
+
+    public ILocatorAssertions Expect(ILocator locator, string message) => Assertions.Expect(locator, message);
+
+    public IPageAssertions Expect(IPage page, string message) => Assertions.Expect(page, message);
+
+    public IAPIResponseAssertions Expect(IAPIResponse response, string message) => Assertions.Expect(response, message);
 }
diff --git a/src/Playwright.NUnit/PlaywrightTest.cs b/src/Playwright.NUnit/PlaywrightTest.cs
index 94526676f..15cf59a48 100644
--- a/src/Playwright.NUnit/PlaywrightTest.cs
+++ b/src/Playwright.NUnit/PlaywrightTest.cs
@@ -53,4 +53,10 @@ public async Task PlaywrightSetup()
     public IPageAssertions Expect(IPage page) => Assertions.Expect(page);
 
     public IAPIResponseAssertions Expect(IAPIResponse response) => Assertions.Expect(response);
+
+    public ILocatorAssertions Expect(ILocator locator, string message) => Assertions.Expect(locator, message);
+
+    public IPageAssertions Expect(IPage page, string message) => Assertions.Expect(page, message);
+
+    public IAPIResponseAssertions Expect(IAPIResponse response, string message) => Assertions.Expect(response, message);
 }
diff --git a/src/Playwright.Tests/Assertions/LocatorAssertionsTests.cs b/src/Playwright.Tests/Assertions/LocatorAssertionsTests.cs
index 97eea0aff..b84b58df6 100644
--- a/src/Playwright.Tests/Assertions/LocatorAssertionsTests.cs
+++ b/src/Playwright.Tests/Assertions/LocatorAssertionsTests.cs
@@ -73,6 +73,24 @@ public async Task FailWithIndeterminateTrue()
         StringAssert.Contains("Expect \"ToBeCheckedAsync\" with timeout 1000ms", exception.Message);
     }
 
+    [PlaywrightTest("playwright-test/playwright.expect.spec.ts", "should support a custom expect message")]
+    public async Task ShouldSupportCustomExpectMessage()
+    {
+        await Page.SetContentAsync("<div></div>");
+        var locator = Page.Locator("input");
+        var exception = await PlaywrightAssert.ThrowsAsync<PlaywrightException>(
+            () => Expect(locator, "should be logged in").ToBeVisibleAsync(new() { Timeout = 1000 }));
+        StringAssert.StartsWith("should be logged in", exception.Message);
+        StringAssert.Contains("Locator expected to be visible", exception.Message);
+
+        // Custom message also propagates through Not.
+        await Page.SetContentAsync("<input>");
+        var present = Page.Locator("input");
+        var notException = await PlaywrightAssert.ThrowsAsync<PlaywrightException>(
+            () => Expect(present, "should not be present").Not.ToBeVisibleAsync(new() { Timeout = 1000 }));
+        StringAssert.StartsWith("should not be present", notException.Message);
+    }
+
     [PlaywrightTest("playwright-test/playwright.expect.spec.ts", "should be able to set default timeout")]
     public async Task ShouldBeAbleToSetDefaultTimeout()
     {
diff --git a/src/Playwright.Xunit.v3/PlaywrightTest.cs b/src/Playwright.Xunit.v3/PlaywrightTest.cs
index 0c99831ca..532f79245 100644
--- a/src/Playwright.Xunit.v3/PlaywrightTest.cs
+++ b/src/Playwright.Xunit.v3/PlaywrightTest.cs
@@ -52,4 +52,10 @@ public override async ValueTask InitializeAsync()
     public IPageAssertions Expect(IPage page) => Assertions.Expect(page);
 
     public IAPIResponseAssertions Expect(IAPIResponse response) => Assertions.Expect(response);
+
+    public ILocatorAssertions Expect(ILocator locator, string message) => Assertions.Expect(locator, message);
+
+    public IPageAssertions Expect(IPage page, string message) => Assertions.Expect(page, message);
+
+    public IAPIResponseAssertions Expect(IAPIResponse response, string message) => Assertions.Expect(response, message);
 }
diff --git a/src/Playwright.Xunit/PlaywrightTest.cs b/src/Playwright.Xunit/PlaywrightTest.cs
index e4b8ae5b1..08967132f 100644
--- a/src/Playwright.Xunit/PlaywrightTest.cs
+++ b/src/Playwright.Xunit/PlaywrightTest.cs
@@ -52,4 +52,10 @@ public override async Task InitializeAsync()
     public IPageAssertions Expect(IPage page) => Assertions.Expect(page);
 
     public IAPIResponseAssertions Expect(IAPIResponse response) => Assertions.Expect(response);
+
+    public ILocatorAssertions Expect(ILocator locator, string message) => Assertions.Expect(locator, message);
+
+    public IPageAssertions Expect(IPage page, string message) => Assertions.Expect(page, message);
+
+    public IAPIResponseAssertions Expect(IAPIResponse response, string message) => Assertions.Expect(response, message);
 }
diff --git a/src/Playwright/Assertions.cs b/src/Playwright/Assertions.cs
index 9fa016b3f..12c51c9ad 100644
--- a/src/Playwright/Assertions.cs
+++ b/src/Playwright/Assertions.cs
@@ -44,4 +44,23 @@ public static class Assertions
     public static IPageAssertions Expect(IPage page) => new PageAssertions(page, false);
 
     public static IAPIResponseAssertions Expect(IAPIResponse response) => new APIResponseAssertions(response, false);
+
+    /// <summary>
+    /// Creates assertions that prefix any failure message with <paramref name="message"/>, providing
+    /// extra context in test reports.
+    /// </summary>
+    /// <param name="locator">The locator to assert against.</param>
+    /// <param name="message">Message to prepend to any assertion failure.</param>
+    /// <returns>Assertions for the given locator.</returns>
+    public static ILocatorAssertions Expect(ILocator locator, string message) => new LocatorAssertions(locator, false, message);
+
+    /// <inheritdoc cref="Expect(ILocator, string)" />
+    /// <param name="page">The page to assert against.</param>
+    /// <param name="message">Message to prepend to any assertion failure.</param>
+    public static IPageAssertions Expect(IPage page, string message) => new PageAssertions(page, false, message);
+
+    /// <inheritdoc cref="Expect(ILocator, string)" />
+    /// <param name="response">The API response to assert against.</param>
+    /// <param name="message">Message to prepend to any assertion failure.</param>
+    public static IAPIResponseAssertions Expect(IAPIResponse response, string message) => new APIResponseAssertions(response, false, message);
 }
diff --git a/src/Playwright/Core/APIResponseAssertions.cs b/src/Playwright/Core/APIResponseAssertions.cs
index e12998000..01c324c43 100644
--- a/src/Playwright/Core/APIResponseAssertions.cs
+++ b/src/Playwright/Core/APIResponseAssertions.cs
@@ -33,8 +33,9 @@ internal class APIResponseAssertions : IAPIResponseAssertions
 {
     private readonly APIResponse _actual;
     private readonly bool _isNot;
+    private readonly string? _customMessage;
 
-    public APIResponseAssertions(IAPIResponse response, bool isNot)
+    public APIResponseAssertions(IAPIResponse response, bool isNot, string? customMessage = null)
     {
         if (response == null)
         {
@@ -42,9 +43,10 @@ public APIResponseAssertions(IAPIResponse response, bool isNot)
         }
         _actual = (APIResponse)response;
         _isNot = isNot;
+        _customMessage = customMessage;
     }
 
-    public IAPIResponseAssertions Not => new APIResponseAssertions(_actual, !_isNot);
+    public IAPIResponseAssertions Not => new APIResponseAssertions(_actual, !_isNot, _customMessage);
 
     public async Task ToBeOKAsync()
     {
@@ -72,7 +74,8 @@ public async Task ToBeOKAsync()
                 responseText = $"\nResponse text:\n{trimmedText}";
             }
         }
-        throw new PlaywrightException(message + responseText);
+        var prefix = _customMessage != null ? _customMessage + "\n\n" : string.Empty;
+        throw new PlaywrightException(prefix + message + responseText);
     }
 
     private static bool IsTextualMimeType(string contentType)
diff --git a/src/Playwright/Core/AssertionsBase.cs b/src/Playwright/Core/AssertionsBase.cs
index bfb1a2b9e..c6527835b 100644
--- a/src/Playwright/Core/AssertionsBase.cs
+++ b/src/Playwright/Core/AssertionsBase.cs
@@ -44,13 +44,16 @@ internal abstract class AssertionsBase
 {
     private static float _defaultTimeout = 5_000;
 
-    public AssertionsBase(bool isNot)
+    public AssertionsBase(bool isNot, string? customMessage = null)
     {
         IsNot = isNot;
+        CustomMessage = customMessage;
     }
 
     protected bool IsNot { get; }
 
+    protected string? CustomMessage { get; }
+
     protected abstract Task<FrameExpectResult> CallExpectAsync(string expression, FrameExpectOptions expectOptions, string title);
 
     protected async Task ExpectImplAsync(string expression, ExpectedTextValue textValue, object expected, string message, string title, FrameExpectOptions options)
@@ -85,11 +88,12 @@ protected async Task ExpectImplAsync(string expression, FrameExpectOptions expec
             {
                 message += "\n" + result.ErrorMessage;
             }
+            var prefix = CustomMessage != null ? CustomMessage + "\n\n" : string.Empty;
             if (expected == null)
             {
-                throw new PlaywrightException($"{message} {log}");
+                throw new PlaywrightException($"{prefix}{message} {log}");
             }
-            throw new PlaywrightException($"{message} '{FormatValue(expected)}'\nBut was: '{FormatValue(actual)}' {log}");
+            throw new PlaywrightException($"{prefix}{message} '{FormatValue(expected)}'\nBut was: '{FormatValue(actual)}' {log}");
         }
     }
 
diff --git a/src/Playwright/Core/LocatorAssertions.cs b/src/Playwright/Core/LocatorAssertions.cs
index 9ebc9beae..f1aa62c0c 100644
--- a/src/Playwright/Core/LocatorAssertions.cs
+++ b/src/Playwright/Core/LocatorAssertions.cs
@@ -32,14 +32,14 @@ namespace Microsoft.Playwright.Core;
 
 internal class LocatorAssertions : AssertionsBase, ILocatorAssertions
 {
-    public LocatorAssertions(ILocator locator, bool isNot) : base(isNot)
+    public LocatorAssertions(ILocator locator, bool isNot, string? customMessage = null) : base(isNot, customMessage)
     {
         ActualLocator = (Locator)locator;
     }
 
     private Locator ActualLocator { get; }
 
-    public ILocatorAssertions Not => new LocatorAssertions(ActualLocator, !IsNot);
+    public ILocatorAssertions Not => new LocatorAssertions(ActualLocator, !IsNot, CustomMessage);
 
     protected override Task<FrameExpectResult> CallExpectAsync(string expression, FrameExpectOptions expectOptions, string title)
     {
diff --git a/src/Playwright/Core/PageAssertions.cs b/src/Playwright/Core/PageAssertions.cs
index a20c1e30e..8d283fca9 100644
--- a/src/Playwright/Core/PageAssertions.cs
+++ b/src/Playwright/Core/PageAssertions.cs
@@ -33,12 +33,12 @@ internal class PageAssertions : AssertionsBase, IPageAssertions
 {
     private readonly Page _page;
 
-    public PageAssertions(IPage page, bool isNot) : base(isNot)
+    public PageAssertions(IPage page, bool isNot, string? customMessage = null) : base(isNot, customMessage)
     {
         _page = (Page)page;
     }
 
-    public IPageAssertions Not => new PageAssertions(_page, !IsNot);
+    public IPageAssertions Not => new PageAssertions(_page, !IsNot, CustomMessage);
 
     protected override Task<FrameExpectResult> CallExpectAsync(string expression, FrameExpectOptions expectOptions, string title)
     {