diff --git a/src/Middleware/ResponseCompression/src/ResponseCompressionBody.cs b/src/Middleware/ResponseCompression/src/ResponseCompressionBody.cs
index 2eefdb6482b8..671c81231043 100644
--- a/src/Middleware/ResponseCompression/src/ResponseCompressionBody.cs
+++ b/src/Middleware/ResponseCompression/src/ResponseCompressionBody.cs
@@ -196,15 +196,18 @@ public override async ValueTask WriteAsync(ReadOnlyMemory<byte> buffer, Cancella
     }
 
     /// <summary>
-    /// Checks if the response should be compressed and sets the response headers.
+    /// Examines the response on first write to see if compression should be used and if true sets the Vary Accept-Encoding header.
     /// </summary>
-    /// <returns>The compression provider to use if compression is enabled, otherwise null.</returns>
-    private ICompressionProvider? InitializeCompressionHeaders()
+    /// <param name="provider">current response compression provider</param>
+    /// <param name="context">The <see cref="HttpContext"/>.</param>
+    /// <returns><see langword="true" /> if the response should be compressed, otherwise <see langword="false" />.</returns>
+    internal static bool ShouldCompressResponseCommon(IResponseCompressionProvider provider, HttpContext context)
     {
-        if (_provider.ShouldCompressResponse(_context))
+        var result = provider.ShouldCompressResponse(context);
+
+        if (result)
         {
-            var headers = _context.Response.Headers;
-            // If the MIME type indicates that the response could be compressed, caches will need to vary by the Accept-Encoding header
+            var headers = context.Response.Headers;
             var varyValues = headers.GetCommaSeparatedValues(HeaderNames.Vary);
             var varyByAcceptEncoding = false;
 
@@ -219,10 +222,22 @@ public override async ValueTask WriteAsync(ReadOnlyMemory<byte> buffer, Cancella
 
             if (!varyByAcceptEncoding)
             {
-                // Can't use += as StringValues does not override operator+
-                // and the implict conversions will cause an incorrect string concat https://github.com/dotnet/runtime/issues/52507
                 headers.Vary = StringValues.Concat(headers.Vary, HeaderNames.AcceptEncoding);
             }
+        }
+
+        return result;
+    }
+
+    /// <summary>
+    /// Checks if the response should be compressed and sets the response headers.
+    /// </summary>
+    /// <returns>The compression provider to use if compression is enabled, otherwise null.</returns>
+    private ICompressionProvider? InitializeCompressionHeaders()
+    {
+        if (ShouldCompressResponseCommon(_provider, _context))
+        {
+            var headers = _context.Response.Headers;
 
             var compressionProvider = ResolveCompressionProvider();
             if (compressionProvider != null)
diff --git a/src/Middleware/ResponseCompression/src/ResponseCompressionMiddleware.cs b/src/Middleware/ResponseCompression/src/ResponseCompressionMiddleware.cs
index 22a9677d6e10..519c508f5187 100644
--- a/src/Middleware/ResponseCompression/src/ResponseCompressionMiddleware.cs
+++ b/src/Middleware/ResponseCompression/src/ResponseCompressionMiddleware.cs
@@ -38,11 +38,19 @@ public Task Invoke(HttpContext context)
     {
         if (!_provider.CheckRequestAcceptsCompression(context))
         {
+            var originalResponseFeature = context.Features.GetRequiredFeature<IHttpResponseFeature>();
+            originalResponseFeature.OnStarting(OnStartingResponseHandler, context);
             return _next(context);
         }
         return InvokeCore(context);
     }
 
+    private async Task OnStartingResponseHandler(object state)
+    {
+        HttpContext context = (HttpContext)state;
+        ResponseCompressionBody.ShouldCompressResponseCommon(_provider, context);
+    }
+
     private async Task InvokeCore(HttpContext context)
     {
         var originalBodyFeature = context.Features.Get<IHttpResponseBodyFeature>();
diff --git a/src/Middleware/ResponseCompression/test/ResponseCompressionMiddlewareTest.cs b/src/Middleware/ResponseCompression/test/ResponseCompressionMiddlewareTest.cs
index 4f1d1def09fc..156ad4ae22a3 100644
--- a/src/Middleware/ResponseCompression/test/ResponseCompressionMiddlewareTest.cs
+++ b/src/Middleware/ResponseCompression/test/ResponseCompressionMiddlewareTest.cs
@@ -41,12 +41,14 @@ public void Options_HttpsDisabledByDefault()
     }
 
     [Fact]
-    public async Task Request_NoAcceptEncoding_Uncompressed()
+    public async Task Request_NoAcceptEncoding_Uncompressed_WithVaryHeader()
     {
         var (response, logMessages) = await InvokeMiddleware(100, requestAcceptEncodings: null, responseType: TextPlain);
 
-        CheckResponseNotCompressed(response, expectedBodyLength: 100, sendVaryHeader: false);
-        AssertLog(logMessages.Single(), LogLevel.Debug, "No response compression available, the Accept-Encoding header is missing or invalid.");
+        CheckResponseNotCompressed(response, expectedBodyLength: 100, sendVaryHeader: true);
+        Assert.Equal(2, logMessages.Count);
+        AssertLog(logMessages.First(), LogLevel.Debug, "No response compression available, the Accept-Encoding header is missing or invalid.");
+        AssertLog(logMessages.Skip(1).First(), LogLevel.Trace, "Response compression is available for this Content-Type.");
     }
 
     [Fact]
@@ -132,12 +134,14 @@ public async Task Request_AcceptUnknown_NotCompressed()
     }
 
     [Fact]
-    public async Task RequestHead_NoAcceptEncoding_Uncompressed()
+    public async Task RequestHead_NoAcceptEncoding_Uncompressed_WithVaryHeader()
     {
         var (response, logMessages) = await InvokeMiddleware(100, requestAcceptEncodings: null, responseType: TextPlain, httpMethod: HttpMethods.Head);
 
-        CheckResponseNotCompressed(response, expectedBodyLength: 100, sendVaryHeader: false);
-        AssertLog(logMessages.Single(), LogLevel.Debug, "No response compression available, the Accept-Encoding header is missing or invalid.");
+        CheckResponseNotCompressed(response, expectedBodyLength: 100, sendVaryHeader: true);
+        Assert.Equal(2, logMessages.Count);
+        AssertLog(logMessages.First(), LogLevel.Debug, "No response compression available, the Accept-Encoding header is missing or invalid.");
+        AssertLog(logMessages.Skip(1).First(), LogLevel.Trace, "Response compression is available for this Content-Type.");
     }
 
     [Fact]