diff --git a/src/Libraries/Microsoft.Extensions.AI/ChatCompletion/CachingChatClient.cs b/src/Libraries/Microsoft.Extensions.AI/ChatCompletion/CachingChatClient.cs
index 211fc39ec85..2923b0ad62d 100644
--- a/src/Libraries/Microsoft.Extensions.AI/ChatCompletion/CachingChatClient.cs
+++ b/src/Libraries/Microsoft.Extensions.AI/ChatCompletion/CachingChatClient.cs
@@ -51,7 +51,7 @@ public override Task<ChatResponse> GetResponseAsync(
     {
         _ = Throw.IfNull(messages);
 
-        return UseCaching(options) ?
+        return EnableCaching(messages, options) ?
             GetCachedResponseAsync(messages, options, cancellationToken) :
             base.GetResponseAsync(messages, options, cancellationToken);
     }
@@ -79,7 +79,7 @@ public override IAsyncEnumerable<ChatResponseUpdate> GetStreamingResponseAsync(
     {
         _ = Throw.IfNull(messages);
 
-        return UseCaching(options) ?
+        return EnableCaching(messages, options) ?
             GetCachedStreamingResponseAsync(messages, options, cancellationToken) :
             base.GetStreamingResponseAsync(messages, options, cancellationToken);
     }
@@ -196,12 +196,25 @@ private async IAsyncEnumerable<ChatResponseUpdate> GetCachedStreamingResponseAsy
     /// <exception cref="ArgumentNullException"><paramref name="value"/> is <see langword="null"/>.</exception>
     protected abstract Task WriteCacheStreamingAsync(string key, IReadOnlyList<ChatResponseUpdate> value, CancellationToken cancellationToken);
 
-    /// <summary>Determine whether to use caching with the request.</summary>
-    private static bool UseCaching(ChatOptions? options)
+    /// <summary>Determines whether caching should be used with the specified request.</summary>
+    /// <param name="messages">The sequence of chat messages included in the request.</param>
+    /// <param name="options">The chat options included in the request.</param>
+    /// <returns>
+    /// <see langword="true"/> if caching should be used for the request, such that the <see cref="CachingChatClient"/>
+    /// will try to satisfy the request from the cache, or if it can't, will try to cache the fetched response.
+    /// <see langword="false"/> if caching should not be used for the request, such that the request will
+    /// be passed through to the inner <see cref="IChatClient"/> without attempting to read from or write to the cache.
+    /// </returns>
+    /// <remarks>
+    /// The default implementation returns <see langword="true"/> as long as the <paramref name="options"/>
+    /// does not have a <see cref="ChatOptions.ConversationId"/> set.
+    /// </remarks>
+    protected virtual bool EnableCaching(IEnumerable<ChatMessage> messages, ChatOptions? options)
     {
         // We want to skip caching if options.ConversationId is set. If it's set, that implies there's
         // some state that will impact the response and that's not represented in the messages. Since
-        // that state could change even with the same ID, we have to assume caching isn't valid.
+        // that state could change even with the same ID (e.g. if it's a thread ID representing the
+        // mutable state of a conversation), we have to assume caching isn't valid.
         return options?.ConversationId is null;
     }
 }
diff --git a/src/Libraries/Microsoft.Extensions.AI/Microsoft.Extensions.AI.json b/src/Libraries/Microsoft.Extensions.AI/Microsoft.Extensions.AI.json
index 5dcad329637..f7f246eb35c 100644
--- a/src/Libraries/Microsoft.Extensions.AI/Microsoft.Extensions.AI.json
+++ b/src/Libraries/Microsoft.Extensions.AI/Microsoft.Extensions.AI.json
@@ -16,6 +16,10 @@
           "Member": "abstract string Microsoft.Extensions.AI.CachingChatClient.GetCacheKey(System.Collections.Generic.IEnumerable<Microsoft.Extensions.AI.ChatMessage> messages, Microsoft.Extensions.AI.ChatOptions? options, params System.ReadOnlySpan<object?> additionalValues);",
           "Stage": "Stable"
         },
+        {
+          "Member": "virtual bool Microsoft.Extensions.AI.CachingChatClient.EnableCaching(System.Collections.Generic.IEnumerable<Microsoft.Extensions.AI.ChatMessage> messages, Microsoft.Extensions.AI.ChatOptions? options);",
+          "Stage": "Stable"
+        },
         {
           "Member": "override System.Threading.Tasks.Task<Microsoft.Extensions.AI.ChatResponse> Microsoft.Extensions.AI.CachingChatClient.GetResponseAsync(System.Collections.Generic.IEnumerable<Microsoft.Extensions.AI.ChatMessage> messages, Microsoft.Extensions.AI.ChatOptions? options = null, System.Threading.CancellationToken cancellationToken = default(System.Threading.CancellationToken));",
           "Stage": "Stable"
diff --git a/test/Libraries/Microsoft.Extensions.AI.Tests/ChatCompletion/DistributedCachingChatClientTest.cs b/test/Libraries/Microsoft.Extensions.AI.Tests/ChatCompletion/DistributedCachingChatClientTest.cs
index 4f2427d133c..2c755da7be9 100644
--- a/test/Libraries/Microsoft.Extensions.AI.Tests/ChatCompletion/DistributedCachingChatClientTest.cs
+++ b/test/Libraries/Microsoft.Extensions.AI.Tests/ChatCompletion/DistributedCachingChatClientTest.cs
@@ -33,9 +33,11 @@ public void Ctor_ExpectedDefaults()
     }
 
     [Theory]
-    [InlineData(false)]
-    [InlineData(true)]
-    public async Task CachesSuccessResultsAsync(bool conversationIdSet)
+    [InlineData(false, false)]
+    [InlineData(false, true)]
+    [InlineData(true, false)]
+    [InlineData(true, true)]
+    public async Task CachesSuccessResultsAsync(bool conversationIdSet, bool customCaching)
     {
         // Arrange
         ChatOptions options = new() { ConversationId = conversationIdSet ? "123" : null };
@@ -79,10 +81,16 @@ public async Task CachesSuccessResultsAsync(bool conversationIdSet)
                 return Task.FromResult(expectedResponse);
             }
         };
-        using var outer = new DistributedCachingChatClient(testClient, _storage)
-        {
-            JsonSerializerOptions = TestJsonSerializerContext.Default.Options
-        };
+
+        int enableCachingInvocations = 0;
+        using var outer = customCaching ?
+            new CustomCachingChatClient(testClient, _storage, (m, o) =>
+            {
+                return ++enableCachingInvocations % 2 == 0;
+            }) :
+            new DistributedCachingChatClient(testClient, _storage);
+
+        outer.JsonSerializerOptions = TestJsonSerializerContext.Default.Options;
 
         // Make the initial request and do a quick sanity check
         var result1 = await outer.GetResponseAsync("some input", options);
@@ -93,12 +101,28 @@ public async Task CachesSuccessResultsAsync(bool conversationIdSet)
         var result2 = await outer.GetResponseAsync("some input", options);
 
         // Assert
-        Assert.Equal(conversationIdSet ? 2 : 1, innerCallCount);
+        if (customCaching)
+        {
+            Assert.Equal(enableCachingInvocations % 2 == 0 ? 2 : 1, innerCallCount);
+        }
+        else
+        {
+            Assert.Equal(conversationIdSet ? 2 : 1, innerCallCount);
+        }
+
         AssertResponsesEqual(expectedResponse, result2);
 
         // Act/Assert 2: Cache misses do not return cached results
         await outer.GetResponseAsync("some modified input", options);
-        Assert.Equal(conversationIdSet ? 3 : 2, innerCallCount);
+        Assert.Equal(conversationIdSet || customCaching ? 3 : 2, innerCallCount);
+
+        Assert.Equal(customCaching ? 3 : 0, enableCachingInvocations);
+    }
+
+    private sealed class CustomCachingChatClient(IChatClient innerClient, IDistributedCache storage, Func<IEnumerable<ChatMessage>, ChatOptions?, bool> enableCaching) :
+        DistributedCachingChatClient(innerClient, storage)
+    {
+        protected override bool EnableCaching(IEnumerable<ChatMessage> messages, ChatOptions? options) => enableCaching(messages, options);
     }
 
     [Fact]