diff --git a/src/HttpClientFactory/Polly/src/PolicyHttpMessageHandler.cs b/src/HttpClientFactory/Polly/src/PolicyHttpMessageHandler.cs
index f2de2588d944..8f973a98db21 100644
--- a/src/HttpClientFactory/Polly/src/PolicyHttpMessageHandler.cs
+++ b/src/HttpClientFactory/Polly/src/PolicyHttpMessageHandler.cs
@@ -1,4 +1,4 @@
-// Licensed to the .NET Foundation under one or more agreements.
+// Licensed to the .NET Foundation under one or more agreements.
 // The .NET Foundation licenses this file to you under the MIT license.
 
 using System;
@@ -73,6 +73,7 @@ namespace Microsoft.Extensions.Http
     /// </remarks>
     public class PolicyHttpMessageHandler : DelegatingHandler
     {
+        private const string PriorResponseKey = "PolicyHttpMessageHandler.PriorResponse";
         private readonly IAsyncPolicy<HttpResponseMessage> _policy;
         private readonly Func<HttpRequestMessage, IAsyncPolicy<HttpResponseMessage>> _policySelector;
 
@@ -147,7 +148,7 @@ protected override async Task<HttpResponseMessage> SendAsync(HttpRequestMessage
         /// <param name="context">The <see cref="Context"/>.</param>
         /// <param name="cancellationToken">The <see cref="CancellationToken"/>.</param>
         /// <returns>Returns a <see cref="Task{HttpResponseMessage}"/> that will yield a response when completed.</returns>
-        protected virtual Task<HttpResponseMessage> SendCoreAsync(HttpRequestMessage request, Context context, CancellationToken cancellationToken)
+        protected virtual async Task<HttpResponseMessage> SendCoreAsync(HttpRequestMessage request, Context context, CancellationToken cancellationToken)
         {
             if (request == null)
             {
@@ -159,7 +160,18 @@ protected virtual Task<HttpResponseMessage> SendCoreAsync(HttpRequestMessage req
                 throw new ArgumentNullException(nameof(context));
             }
 
-            return base.SendAsync(request, cancellationToken);
+            if (request.Properties.TryGetValue(PriorResponseKey, out var priorResult) && priorResult is IDisposable disposable)
+            {
+                // This is a retry, dispose the prior response to free up the connection.
+                request.Properties.Remove(PriorResponseKey);
+                disposable.Dispose();
+            }
+
+            var result = await base.SendAsync(request, cancellationToken);
+
+            request.Properties.Add(PriorResponseKey, result);
+
+            return result;
         }
 
         private IAsyncPolicy<HttpResponseMessage> SelectPolicy(HttpRequestMessage request)
diff --git a/src/HttpClientFactory/Polly/test/PolicyHttpMessageHandlerTest.cs b/src/HttpClientFactory/Polly/test/PolicyHttpMessageHandlerTest.cs
index c6de301cf913..98965d119d54 100644
--- a/src/HttpClientFactory/Polly/test/PolicyHttpMessageHandlerTest.cs
+++ b/src/HttpClientFactory/Polly/test/PolicyHttpMessageHandlerTest.cs
@@ -7,6 +7,7 @@
 using System.Threading.Tasks;
 using Microsoft.Extensions.Internal;
 using Polly;
+using Polly.Extensions.Http;
 using Polly.Timeout;
 using Xunit;
 
@@ -98,6 +99,54 @@ public async Task SendAsync_DynamicPolicy_PolicyTriggers_CanReexecuteSendAsync()
             Assert.Same(expectedRequest, policySelectorRequest);
         }
 
+        [Fact]
+        public async Task SendAsync_StaticPolicy_PolicyTriggers_CanReexecuteSendAsync_FirstResponseDisposed()
+        {
+            // Arrange
+            var policy = HttpPolicyExtensions.HandleTransientHttpError()
+                .RetryAsync(retryCount: 1);
+
+            var callCount = 0;
+            var fakeContent = new FakeContent();
+            var firstResponse = new HttpResponseMessage()
+            {
+                StatusCode = System.Net.HttpStatusCode.InternalServerError,
+                Content = fakeContent,
+            };
+            var expected = new HttpResponseMessage();
+
+            var handler = new PolicyHttpMessageHandler(policy);
+            handler.InnerHandler = new TestHandler()
+            {
+                OnSendAsync = (req, ct) =>
+                {
+                    if (callCount == 0)
+                    {
+                        callCount++;
+                        return Task.FromResult(firstResponse);
+                    }
+                    else if (callCount == 1)
+                    {
+                        callCount++;
+                        return Task.FromResult(expected);
+                    }
+                    else
+                    {
+                        throw new InvalidOperationException();
+                    }
+                }
+            };
+            var invoke = new HttpMessageInvoker(handler);
+
+            // Act
+            var response = await invoke.SendAsync(new HttpRequestMessage(), CancellationToken.None);
+
+            // Assert
+            Assert.Equal(2, callCount);
+            Assert.Same(expected, response);
+            Assert.True(fakeContent.Disposed);
+        }
+
         [Fact]
         public async Task SendAsync_DynamicPolicy_PolicySelectorReturnsNull_ThrowsException()
         {
@@ -333,5 +382,31 @@ protected override Task<HttpResponseMessage> SendCoreAsync(HttpRequestMessage re
                 return OnSendAsync(request, context, cancellationToken);
             }
         }
+
+        private class TestHandler : HttpMessageHandler
+        {
+            public Func<HttpRequestMessage, CancellationToken, Task<HttpResponseMessage>> OnSendAsync { get; set; }
+
+            protected override Task<HttpResponseMessage> SendAsync(HttpRequestMessage request, CancellationToken cancellationToken)
+            {
+                Assert.NotNull(OnSendAsync);
+                return OnSendAsync(request, cancellationToken);
+            }
+        }
+
+        private class FakeContent : StringContent
+        {
+            public FakeContent() : base("hello world")
+            {
+            }
+
+            public bool Disposed { get; set; }
+
+            protected override void Dispose(bool disposing)
+            {
+                Disposed = true;
+                base.Dispose(disposing);
+            }
+        }
     }
 }