diff --git a/src/TestFramework/TestFramework/Assertions/Assert.Contains.cs b/src/TestFramework/TestFramework/Assertions/Assert.Contains.cs
index 849d9a4bac..8d05c96293 100644
--- a/src/TestFramework/TestFramework/Assertions/Assert.Contains.cs
+++ b/src/TestFramework/TestFramework/Assertions/Assert.Contains.cs
@@ -178,6 +178,22 @@ public static T ContainsSingle<T>(Func<T, bool> predicate, IEnumerable<T> collec
     public static void Contains<T>(T expected, IEnumerable<T> collection)
         => Contains(expected, collection, string.Empty, null);
 
+    /// <summary>
+    /// Tests whether the specified non-generic key/value pair collection contains the given key.
+    /// </summary>
+    /// <param name="expectedKey">The expected item.</param>
+    /// <param name="collection">The non-generic key/value pair collection (like Hashset).</param>
+    public static void ContainsKey(object expectedKey, IEnumerable collection)
+        => ContainsKey(expectedKey, collection, string.Empty);
+
+    /// <summary>
+    /// Tests whether the specified non-generic key/value pair collection contains the given value.
+    /// </summary>
+    /// <param name="expectedValue">The expected item.</param>
+    /// <param name="collection">The non-generic key/value pair collection (like Hashset).</param>
+    public static void ContainsValue(object expectedValue, IEnumerable collection)
+        => ContainsValue(expectedValue, collection, string.Empty);
+
     /// <summary>
     /// Tests whether the specified collection contains the given element.
     /// </summary>
@@ -244,6 +260,66 @@ public static void Contains<T>(T expected, IEnumerable<T> collection, IEqualityC
         }
     }
 
+    /// <summary>
+    /// Tests whether the specified collection contains the given key.
+    /// Specifically for non-generic key/value pair collections like Hashtable.
+    /// </summary>
+    /// <param name="expectedKey">The expected key.</param>
+    /// <param name="collection">The non-generic key/value pair collection.</param>
+    /// <param name="message">The message format to display when the assertion fails.</param>
+    public static void ContainsKey(object expectedKey, IEnumerable collection, string? message)
+    {
+        bool isFound = false;
+
+        foreach (object? item in collection)
+        {
+            if (item is DictionaryEntry dictEntry)
+            {
+                if (object.Equals(expectedKey, dictEntry.Key))
+                {
+                    isFound = true;
+                    break;
+                }
+            }
+        }
+
+        if (!isFound)
+        {
+            string userMessage = BuildUserMessage(message);
+            ThrowAssertContainsItemFailed(userMessage);
+        }
+    }
+
+    /// <summary>
+    /// Tests whether the specified collection contains the given key.
+    /// Specifically for non-generic key/value pair collections like Hashtable.
+    /// </summary>
+    /// <param name="expectedValue">The expected value.</param>
+    /// <param name="collection">The non-generic key/value pair collection.</param>
+    /// <param name="message">The message format to display when the assertion fails.</param>
+    public static void ContainsValue(object expectedValue, IEnumerable collection, string? message)
+    {
+        bool isFound = false;
+
+        foreach (object? item in collection)
+        {
+            if (item is DictionaryEntry dictEntry)
+            {
+                if (object.Equals(expectedValue, dictEntry.Value))
+                {
+                    isFound = true;
+                    break;
+                }
+            }
+        }
+
+        if (!isFound)
+        {
+            string userMessage = BuildUserMessage(message);
+            ThrowAssertContainsItemFailed(userMessage);
+        }
+    }
+
     /// <summary>
     /// Tests whether the specified collection contains the given element.
     /// </summary>
diff --git a/src/TestFramework/TestFramework/PublicAPI/PublicAPI.Unshipped.txt b/src/TestFramework/TestFramework/PublicAPI/PublicAPI.Unshipped.txt
index 7d27ebf1af..ae0a3304ae 100644
--- a/src/TestFramework/TestFramework/PublicAPI/PublicAPI.Unshipped.txt
+++ b/src/TestFramework/TestFramework/PublicAPI/PublicAPI.Unshipped.txt
@@ -1,5 +1,9 @@
 #nullable enable
 Microsoft.VisualStudio.TestTools.UnitTesting.DynamicDataSourceType.Field = 3 -> Microsoft.VisualStudio.TestTools.UnitTesting.DynamicDataSourceType
+static Microsoft.VisualStudio.TestTools.UnitTesting.Assert.ContainsKey(object! expectedKey, System.Collections.IEnumerable! collection) -> void
+static Microsoft.VisualStudio.TestTools.UnitTesting.Assert.ContainsKey(object! expectedKey, System.Collections.IEnumerable! collection, string? message) -> void
+static Microsoft.VisualStudio.TestTools.UnitTesting.Assert.ContainsValue(object! expectedValue, System.Collections.IEnumerable! collection) -> void
+static Microsoft.VisualStudio.TestTools.UnitTesting.Assert.ContainsValue(object! expectedValue, System.Collections.IEnumerable! collection, string? message) -> void
 *REMOVED*static Microsoft.VisualStudio.TestTools.UnitTesting.Assert.Instance.get -> Microsoft.VisualStudio.TestTools.UnitTesting.Assert!
 *REMOVED*static Microsoft.VisualStudio.TestTools.UnitTesting.CollectionAssert.Instance.get -> Microsoft.VisualStudio.TestTools.UnitTesting.CollectionAssert!
 *REMOVED*static Microsoft.VisualStudio.TestTools.UnitTesting.StringAssert.Instance.get -> Microsoft.VisualStudio.TestTools.UnitTesting.StringAssert!
diff --git a/test/UnitTests/TestFramework.UnitTests/Assertions/AssertTests.Contains.cs b/test/UnitTests/TestFramework.UnitTests/Assertions/AssertTests.Contains.cs
index b751807d44..a6eb5961fe 100644
--- a/test/UnitTests/TestFramework.UnitTests/Assertions/AssertTests.Contains.cs
+++ b/test/UnitTests/TestFramework.UnitTests/Assertions/AssertTests.Contains.cs
@@ -362,6 +362,99 @@ public void Contains_ValueExpected_ItemDoesNotExist_ThrowsException()
         action.Should().Throw<AssertFailedException>().WithMessage("*20*");
     }
 
+    /// <summary>
+    /// Tests the ContainsKey method (value overload) when the expected key is present.
+    /// </summary>
+    public void ContainsKey_InNonGenericKeyValueCollection_KeyExpected_KeyExists_DoesNotThrow()
+    {
+        // Arrange
+        var collection = new Hashtable { { "key1", "value1" }, { "key2", "value2" }, { 3, "value3" } };
+
+        // Act
+        Action action = () => Assert.ContainsKey("key2", collection, "No failure expected");
+
+        // Assert
+        action.Should().NotThrow<AssertFailedException>();
+    }
+
+    /// <summary>
+    /// Tests the ContainsKey method (value overload) when the expected key is present.
+    /// </summary>
+    public void ContainsKey_InNonGenericKeyValueCollection_KeyExpected_KeyExists_DoesNotThrow2()
+    {
+        // Arrange
+        var collection = new Hashtable { { "key1", "value1" }, { "key2", "value2" }, { 3, "value3" } };
+
+        // Act
+        Action action = () => Assert.ContainsKey(3, collection, "No failure expected");
+
+        // Assert
+        action.Should().NotThrow<AssertFailedException>();
+    }
+
+    /// <summary>
+    /// Tests the ContainsKey method (value overload) when the expected key is not present.
+    /// Expects an exception.
+    /// </summary>
+    public void ContainsKey_InNonGenericKeyValueCollection_KeyExpected_KeyDoesNotExists_ThrowException()
+    {
+        // Arrange
+        var collection = new Hashtable { { "key1", "value1" }, { "key2", "value2" }, { 3, "value3" } };
+        object expectedKey = "key3";
+
+        // Act
+        Action action = () => Assert.ContainsKey(expectedKey, collection, $"Item {expectedKey} not found");
+
+        // Assert
+        action.Should().Throw<AssertFailedException>().WithMessage($"*Item {expectedKey} not found*");
+    }
+
+    /// <summary>
+    /// Tests the ContainsValue method (value overload) when the expected value is present.
+    /// </summary>
+    public void ContainsValue_InNonGenericKeyValueCollection_ValueExpected_ValueExists_DoesNotThrow()
+    {
+        // Arrange
+        var collection = new Hashtable { { "key1", 1 }, { "key2", "value2" }, { 3, "value3" } };
+
+        // Act
+        Action action = () => Assert.ContainsValue("value2", collection, "No failure expected");
+
+        // Assert
+        action.Should().NotThrow<AssertFailedException>();
+    }
+
+    /// <summary>
+    /// Tests the ContainsValue method (value overload) when the expected value is present.
+    /// </summary>
+    public void ContainsValue_InNonGenericKeyValueCollection_ValueExpected_ValueExists_DoesNotThrow2()
+    {
+        // Arrange
+        var collection = new Hashtable { { "key1", 1 }, { "key2", "value2" }, { 3, "value3" } };
+
+        // Act
+        Action action = () => Assert.ContainsValue(1, collection, "No failure expected");
+
+        // Assert
+        action.Should().NotThrow<AssertFailedException>();
+    }
+
+    /// <summary>
+    /// Tests the ContainsValue method (value overload) when the expected value is not present.
+    /// </summary>
+    public void ContainsValue_InNonGenericKeyValueCollection_ValueExpected_ValueDoesNotExists_ThrowException()
+    {
+        // Arrange
+        var collection = new Hashtable { { "key1", 1 }, { "key2", "value2" }, { 3, "value3" } };
+        object expectedValue = "value1";
+
+        // Act
+        Action action = () => Assert.ContainsValue(expectedValue, collection, $"Item {expectedValue} not found");
+
+        // Assert
+        action.Should().Throw<AssertFailedException>().WithMessage($"*Item {expectedValue} not found*");
+    }
+
     /// <summary>
     /// Tests the Contains method with a comparer when the expected item is present.
     /// </summary>