diff --git a/src/libraries/System.Net.Http/src/System/Net/Http/SocketsHttpHandler/HttpConnectionPoolManager.cs b/src/libraries/System.Net.Http/src/System/Net/Http/SocketsHttpHandler/HttpConnectionPoolManager.cs
index 8c2345c45c7164..f88067dc3ad04f 100644
--- a/src/libraries/System.Net.Http/src/System/Net/Http/SocketsHttpHandler/HttpConnectionPoolManager.cs
+++ b/src/libraries/System.Net.Http/src/System/Net/Http/SocketsHttpHandler/HttpConnectionPoolManager.cs
@@ -584,10 +584,17 @@ public HttpConnectionKey(HttpConnectionKind kind, string? host, int port, string
             }
 
             // In the common case, SslHostName (when present) is equal to Host.  If so, don't include in hash.
-            public override int GetHashCode() =>
-                (SslHostName == Host ?
+            public override int GetHashCode()
+            {
+                int hashCode = SslHostName == Host ?
                     HashCode.Combine(Kind, Host, Port, ProxyUri, Identity) :
-                    HashCode.Combine(Kind, Host, Port, SslHostName, ProxyUri, Identity));
+                    HashCode.Combine(Kind, Host, Port, SslHostName, ProxyUri, Identity);
+
+                // Uri equality ignores IPv6 scope IDs, but they identify distinct proxy endpoints.
+                return ProxyUri is { HostNameType: UriHostNameType.IPv6 } proxyUri ?
+                    HashCode.Combine(hashCode, proxyUri.IdnHost) :
+                    hashCode;
+            }
 
             public override bool Equals([NotNullWhen(true)] object? obj) =>
                 obj is HttpConnectionKey hck &&
@@ -598,6 +605,7 @@ public bool Equals(HttpConnectionKey other) =>
                 Host == other.Host &&
                 Port == other.Port &&
                 ProxyUri == other.ProxyUri &&
+                (ProxyUri is not { HostNameType: UriHostNameType.IPv6 } || ProxyUri.IdnHost == other.ProxyUri?.IdnHost) &&
                 SslHostName == other.SslHostName &&
                 Identity == other.Identity;
         }
diff --git a/src/libraries/System.Net.Http/tests/FunctionalTests/HttpConnectionKeyTest.cs b/src/libraries/System.Net.Http/tests/FunctionalTests/HttpConnectionKeyTest.cs
index 3f6a332d754149..cceeac4be4dcac 100644
--- a/src/libraries/System.Net.Http/tests/FunctionalTests/HttpConnectionKeyTest.cs
+++ b/src/libraries/System.Net.Http/tests/FunctionalTests/HttpConnectionKeyTest.cs
@@ -33,5 +33,40 @@ public void Equals_DifferentParameters_ReturnsTrueIfAllEqual(string kindString,
             object actualKey = Activator.CreateInstance(keyType, Enum.Parse(connectionKindType, kindString), host, port, sslHostName, proxyUri, identity);
             Assert.Equal(expected, referenceKey.Equals(actualKey));
         }
+
+        [ConditionalTheory(typeof(SocketsHttpHandler), nameof(SocketsHttpHandler.IsSupported))]
+        [InlineData("http://[fe80::1%1]/", "http://[fe80::1%2]/", false)]
+        [InlineData("http://[fe80::1]/", "http://[fe80::1%1]/", false)]
+        [InlineData("http://[fe80::1%eth0]/", "http://[fe80::1%eth1]/", false)]
+        [InlineData("http://[fe80::1%eth0]/", "http://[fe80::1%ETH0]/", false)]
+        [InlineData("http://[fe80::1%1]/", "http://[fe80::1%1]/", true)]
+        [InlineData("http://[fe80::1%1]/", "HTTP://[fe80:0:0:0:0:0:0:1%1]:80/", true)]
+        [InlineData("http://[fe80::1]/", "http://[fe80:0:0:0:0:0:0:1]:80/", true)]
+        [InlineData("http://user@[fe80::1%1]/#first", "http://other@[fe80::1%1]/#second", true)]
+        [InlineData("http://[fe80::1%1]:80/", "http://[fe80::1%1]:81/", false)]
+        [InlineData("http://[fe80::1%1]/", "https://[fe80::1%1]/", false)]
+        [InlineData("http://[fe80::1%1]/first", "http://[fe80::1%1]/second", false)]
+        [InlineData("http://PROXY.TEST/", "http://proxy.test:80/", true)]
+        [InlineData("http://127.0.0.1/", "http://127.1:80/", true)]
+        public void Equals_ProxyUris_DistinguishesIPv6Scope(string firstProxyUri, string secondProxyUri, bool expected)
+        {
+            Type connectionKindType = Type.GetType("System.Net.Http.HttpConnectionKind, System.Net.Http");
+            Type keyType = Type.GetType("System.Net.Http.HttpConnectionPoolManager+HttpConnectionKey, System.Net.Http");
+            object kind = Enum.Parse(connectionKindType, "Http");
+
+            foreach (string sslHostName in new[] { "localhost", "localhost-ssl" })
+            {
+                object firstKey = Activator.CreateInstance(keyType, kind, "localhost", 80, sslHostName, new Uri(firstProxyUri), string.Empty);
+                object secondKey = Activator.CreateInstance(keyType, kind, "localhost", 80, sslHostName, new Uri(secondProxyUri), string.Empty);
+
+                Assert.Equal(expected, firstKey.Equals(secondKey));
+                Assert.Equal(expected, secondKey.Equals(firstKey));
+                Assert.Equal(expected ? 1 : 2, new HashSet<object> { firstKey, secondKey }.Count);
+                if (expected)
+                {
+                    Assert.Equal(firstKey.GetHashCode(), secondKey.GetHashCode());
+                }
+            }
+        }
     }
 }
diff --git a/src/libraries/System.Net.Http/tests/FunctionalTests/SocketsHttpHandlerTest.cs b/src/libraries/System.Net.Http/tests/FunctionalTests/SocketsHttpHandlerTest.cs
index fb66bb6c6f6955..838bbeb8ff7250 100644
--- a/src/libraries/System.Net.Http/tests/FunctionalTests/SocketsHttpHandlerTest.cs
+++ b/src/libraries/System.Net.Http/tests/FunctionalTests/SocketsHttpHandlerTest.cs
@@ -817,6 +817,49 @@ public sealed class SocketsHttpHandler_HttpClientHandler_Proxy_Test : HttpClient
     {
         public SocketsHttpHandler_HttpClientHandler_Proxy_Test(ITestOutputHelper output) : base(output) { }
 
+        [Theory]
+        [InlineData("http", false, false)]
+        [InlineData("http", true, false)]
+        [InlineData("https", false, false)]
+        [InlineData("https", true, false)]
+        [InlineData("socks5", false, false)]
+        [InlineData("socks5", true, false)]
+        [InlineData("http", false, true)]
+        [InlineData("http", true, true)]
+        [InlineData("https", false, true)]
+        [InlineData("https", true, true)]
+        [InlineData("socks5", false, true)]
+        [InlineData("socks5", true, true)]
+        public async Task Proxy_IPv6ScopeChange_ConnectsToSelectedProxy(string proxyScheme, bool useSsl, bool useHttp2)
+        {
+            var proxy = new WebProxy();
+            using var handler = new SocketsHttpHandler { Proxy = proxy };
+            DnsEndPoint endPoint = null;
+            handler.ConnectCallback = (context, _) =>
+            {
+                endPoint = context.DnsEndPoint;
+                throw new InvalidOperationException(nameof(Proxy_IPv6ScopeChange_ConnectsToSelectedProxy));
+            };
+            using var client = new HttpClient(handler)
+            {
+                DefaultRequestVersion = useHttp2 ? HttpVersion.Version20 : HttpVersion.Version11,
+                DefaultVersionPolicy = HttpVersionPolicy.RequestVersionExact
+            };
+
+            for (int scope = 1; scope <= 2; scope++)
+            {
+                var proxyUri = new Uri($"{proxyScheme}://[fe80::1%{scope}]:8080/");
+                proxy.Address = proxyUri;
+                endPoint = null;
+
+                HttpRequestException exception = await Assert.ThrowsAsync<HttpRequestException>(() => client.GetAsync(useSsl ? "https://example.test/" : "http://example.test/"));
+                Assert.Equal(nameof(Proxy_IPv6ScopeChange_ConnectsToSelectedProxy), Assert.IsType<InvalidOperationException>(exception.InnerException).Message);
+                Assert.NotNull(endPoint);
+                Assert.Equal(IPAddress.Parse(proxyUri.IdnHost), IPAddress.Parse(endPoint.Host));
+                Assert.Equal(proxyUri.Port, endPoint.Port);
+            }
+        }
+
         [Theory]
         [InlineData(true)]
         [InlineData(false)]