diff --git a/src/Libraries/Microsoft.Extensions.AI/ChatCompletion/CachingChatClient.cs b/src/Libraries/Microsoft.Extensions.AI/ChatCompletion/CachingChatClient.cs
index 5aa70e4b262..211fc39ec85 100644
--- a/src/Libraries/Microsoft.Extensions.AI/ChatCompletion/CachingChatClient.cs
+++ b/src/Libraries/Microsoft.Extensions.AI/ChatCompletion/CachingChatClient.cs
@@ -9,6 +9,7 @@
 using Microsoft.Shared.Diagnostics;
 
 #pragma warning disable S127 // "for" loop stop conditions should be invariant
+#pragma warning disable SA1202 // Elements should be ordered by access
 
 namespace Microsoft.Extensions.AI;
 
@@ -45,11 +46,19 @@ protected CachingChatClient(IChatClient innerClient)
     public bool CoalesceStreamingUpdates { get; set; } = true;
 
     /// <inheritdoc />
-    public override async Task<ChatResponse> GetResponseAsync(
+    public override Task<ChatResponse> GetResponseAsync(
         IEnumerable<ChatMessage> messages, ChatOptions? options = null, CancellationToken cancellationToken = default)
     {
         _ = Throw.IfNull(messages);
 
+        return UseCaching(options) ?
+            GetCachedResponseAsync(messages, options, cancellationToken) :
+            base.GetResponseAsync(messages, options, cancellationToken);
+    }
+
+    private async Task<ChatResponse> GetCachedResponseAsync(
+        IEnumerable<ChatMessage> messages, ChatOptions? options = null, CancellationToken cancellationToken = default)
+    {
         // We're only storing the final result, not the in-flight task, so that we can avoid caching failures
         // or having problems when one of the callers cancels but others don't. This has the drawback that
         // concurrent callers might trigger duplicate requests, but that's acceptable.
@@ -65,11 +74,19 @@ public override async Task<ChatResponse> GetResponseAsync(
     }
 
     /// <inheritdoc />
-    public override async IAsyncEnumerable<ChatResponseUpdate> GetStreamingResponseAsync(
-        IEnumerable<ChatMessage> messages, ChatOptions? options = null, [EnumeratorCancellation] CancellationToken cancellationToken = default)
+    public override IAsyncEnumerable<ChatResponseUpdate> GetStreamingResponseAsync(
+        IEnumerable<ChatMessage> messages, ChatOptions? options = null, CancellationToken cancellationToken = default)
     {
         _ = Throw.IfNull(messages);
 
+        return UseCaching(options) ?
+            GetCachedStreamingResponseAsync(messages, options, cancellationToken) :
+            base.GetStreamingResponseAsync(messages, options, cancellationToken);
+    }
+
+    private async IAsyncEnumerable<ChatResponseUpdate> GetCachedStreamingResponseAsync(
+        IEnumerable<ChatMessage> messages, ChatOptions? options = null, [EnumeratorCancellation] CancellationToken cancellationToken = default)
+    {
         if (CoalesceStreamingUpdates)
         {
             // When coalescing updates, we cache non-streaming results coalesced from streaming ones. That means
@@ -178,4 +195,13 @@ public override async IAsyncEnumerable<ChatResponseUpdate> GetStreamingResponseA
     /// <exception cref="ArgumentNullException"><paramref name="key"/> is <see langword="null"/>.</exception>
     /// <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)
+    {
+        // 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.
+        return options?.ConversationId is null;
+    }
 }
diff --git a/test/Libraries/Microsoft.Extensions.AI.Tests/ChatCompletion/DistributedCachingChatClientTest.cs b/test/Libraries/Microsoft.Extensions.AI.Tests/ChatCompletion/DistributedCachingChatClientTest.cs
index 374e617adba..4f2427d133c 100644
--- a/test/Libraries/Microsoft.Extensions.AI.Tests/ChatCompletion/DistributedCachingChatClientTest.cs
+++ b/test/Libraries/Microsoft.Extensions.AI.Tests/ChatCompletion/DistributedCachingChatClientTest.cs
@@ -32,10 +32,13 @@ public void Ctor_ExpectedDefaults()
         Assert.True(cachingClient.CoalesceStreamingUpdates);
     }
 
-    [Fact]
-    public async Task CachesSuccessResultsAsync()
+    [Theory]
+    [InlineData(false)]
+    [InlineData(true)]
+    public async Task CachesSuccessResultsAsync(bool conversationIdSet)
     {
         // Arrange
+        ChatOptions options = new() { ConversationId = conversationIdSet ? "123" : null };
 
         // Verify that all the expected properties will round-trip through the cache,
         // even if this involves serialization
@@ -82,20 +85,20 @@ public async Task CachesSuccessResultsAsync()
         };
 
         // Make the initial request and do a quick sanity check
-        var result1 = await outer.GetResponseAsync("some input");
+        var result1 = await outer.GetResponseAsync("some input", options);
         Assert.Same(expectedResponse, result1);
         Assert.Equal(1, innerCallCount);
 
         // Act
-        var result2 = await outer.GetResponseAsync("some input");
+        var result2 = await outer.GetResponseAsync("some input", options);
 
         // Assert
-        Assert.Equal(1, innerCallCount);
+        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");
-        Assert.Equal(2, innerCallCount);
+        await outer.GetResponseAsync("some modified input", options);
+        Assert.Equal(conversationIdSet ? 3 : 2, innerCallCount);
     }
 
     [Fact]
@@ -207,10 +210,13 @@ public async Task DoesNotCacheCanceledResultsAsync()
         Assert.Equal("A good result", result2.Text);
     }
 
-    [Fact]
-    public async Task StreamingCachesSuccessResultsAsync()
+    [Theory]
+    [InlineData(false)]
+    [InlineData(true)]
+    public async Task StreamingCachesSuccessResultsAsync(bool conversationIdSet)
     {
         // Arrange
+        ChatOptions options = new() { ConversationId = conversationIdSet ? "123" : null };
 
         // Verify that all the expected properties will round-trip through the cache,
         // even if this involves serialization
@@ -255,20 +261,20 @@ public async Task StreamingCachesSuccessResultsAsync()
         };
 
         // Make the initial request and do a quick sanity check
-        var result1 = outer.GetStreamingResponseAsync("some input");
+        var result1 = outer.GetStreamingResponseAsync("some input", options);
         await AssertResponsesEqualAsync(actualUpdate, result1);
         Assert.Equal(1, innerCallCount);
 
         // Act
-        var result2 = outer.GetStreamingResponseAsync("some input");
+        var result2 = outer.GetStreamingResponseAsync("some input", options);
 
         // Assert
-        Assert.Equal(1, innerCallCount);
-        await AssertResponsesEqualAsync(expectedCachedResponse, result2);
+        Assert.Equal(conversationIdSet ? 2 : 1, innerCallCount);
+        await AssertResponsesEqualAsync(conversationIdSet ? actualUpdate : expectedCachedResponse, result2);
 
         // Act/Assert 2: Cache misses do not return cached results
-        await ToListAsync(outer.GetStreamingResponseAsync("some modified input"));
-        Assert.Equal(2, innerCallCount);
+        await ToListAsync(outer.GetStreamingResponseAsync("some modified input", options));
+        Assert.Equal(conversationIdSet ? 3 : 2, innerCallCount);
     }
 
     [Theory]