diff --git a/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs b/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs
index 6fd6d3051a..01b8d831e8 100644
--- a/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs
+++ b/src/Microsoft.AspNetCore.Server.HttpSys/MessagePump.cs
@@ -2,11 +2,9 @@
 // Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
 
 using System;
-using System.Collections.Generic;
 using System.Diagnostics.Contracts;
 using System.Threading;
 using System.Threading.Tasks;
-using Microsoft.AspNetCore.Hosting;
 using Microsoft.AspNetCore.Hosting.Server;
 using Microsoft.AspNetCore.Hosting.Server.Features;
 using Microsoft.AspNetCore.Http.Features;
@@ -69,24 +67,39 @@ namespace Microsoft.AspNetCore.Server.HttpSys
                 throw new ArgumentNullException(nameof(application));
             }
 
-            var serverAdressesPresent = _serverAddresses.Addresses.Count > 0;
+            var hostingUrlsPresent = _serverAddresses.Addresses.Count > 0;
 
-            if (_options.UrlPrefixes.Count > 0)
+            if (_serverAddresses.PreferHostingUrls && hostingUrlsPresent)
             {
-                if (serverAdressesPresent)
+                if (_options.UrlPrefixes.Count > 0)
+                {
+                    LogHelper.LogWarning(_logger, $"Overriding endpoints added to {nameof(HttpSysOptions.UrlPrefixes)} since {nameof(IServerAddressesFeature.PreferHostingUrls)} is set to true." +
+                        $" Binding to address(es) '{string.Join(", ", _serverAddresses.Addresses)}' instead. ");
+
+                    Listener.Options.UrlPrefixes.Clear();
+                }
+
+                foreach (var value in _serverAddresses.Addresses)
+                {
+                    Listener.Options.UrlPrefixes.Add(value);
+                }
+            }
+            else if (_options.UrlPrefixes.Count > 0)
+            {
+                if (hostingUrlsPresent)
                 {
                     LogHelper.LogWarning(_logger, $"Overriding address(es) '{string.Join(", ", _serverAddresses.Addresses)}'. " +
                         $"Binding to endpoints added to {nameof(HttpSysOptions.UrlPrefixes)} instead.");
 
                     _serverAddresses.Addresses.Clear();
+                }
 
-                    foreach (var prefix in _options.UrlPrefixes)
-                    {
-                        _serverAddresses.Addresses.Add(prefix.FullPrefix);
-                    }
+                foreach (var prefix in _options.UrlPrefixes)
+                {
+                    _serverAddresses.Addresses.Add(prefix.FullPrefix);
                 }
             }
-            else if (serverAdressesPresent)
+            else if (hostingUrlsPresent)
             {
                 foreach (var value in _serverAddresses.Addresses)
                 {
diff --git a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/MessagePumpTests.cs b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/MessagePumpTests.cs
index ccbc964607..48913a746f 100644
--- a/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/MessagePumpTests.cs
+++ b/test/Microsoft.AspNetCore.Server.HttpSys.FunctionalTests/MessagePumpTests.cs
@@ -12,6 +12,63 @@ namespace Microsoft.AspNetCore.Server.HttpSys
 {
     public class MessagePumpTests
     {
+        [ConditionalFact]
+        public void OverridingDirectConfigurationWithIServerAddressesFeatureSucceeds()
+        {
+            var serverAddress = "http://localhost:11001/";
+            var overrideAddress = "http://localhost:11002/";
+
+            using (var server = new MessagePump(Options.Create(new HttpSysOptions()), new LoggerFactory()))
+            {
+                var serverAddressesFeature = server.Features.Get<IServerAddressesFeature>();
+                serverAddressesFeature.Addresses.Add(overrideAddress);
+                serverAddressesFeature.PreferHostingUrls = true;
+                server.Listener.Options.UrlPrefixes.Add(serverAddress);
+
+                server.Start(new DummyApplication());
+
+                Assert.Equal(overrideAddress, serverAddressesFeature.Addresses.Single());
+            }
+        }
+
+        [ConditionalTheory]
+        [InlineData("http://localhost:11001/")]
+        [InlineData("invalid address")]
+        [InlineData("")]
+        [InlineData(null)]
+        public void DoesNotOverrideDirectConfigurationWithIServerAddressesFeature_IfPreferHostinUrlsFalse(string overrideAddress)
+        {
+            var serverAddress = "http://localhost:11002/";
+
+            using (var server = new MessagePump(Options.Create(new HttpSysOptions()), new LoggerFactory()))
+            {
+                var serverAddressesFeature = server.Features.Get<IServerAddressesFeature>();
+                serverAddressesFeature.Addresses.Add(overrideAddress);
+                server.Listener.Options.UrlPrefixes.Add(serverAddress);
+
+                server.Start(new DummyApplication());
+
+                Assert.Equal(serverAddress, serverAddressesFeature.Addresses.Single());
+            }
+        }
+
+        [ConditionalFact]
+        public void DoesNotOverrideDirectConfigurationWithIServerAddressesFeature_IfAddressesIsEmpty()
+        {
+            var serverAddress = "http://localhost:11002/";
+
+            using (var server = new MessagePump(Options.Create(new HttpSysOptions()), new LoggerFactory()))
+            {
+                var serverAddressesFeature = server.Features.Get<IServerAddressesFeature>();
+                serverAddressesFeature.PreferHostingUrls = true;
+                server.Listener.Options.UrlPrefixes.Add(serverAddress);
+
+                server.Start(new DummyApplication());
+
+                Assert.Equal(serverAddress, serverAddressesFeature.Addresses.Single());
+            }
+        }
+
         [ConditionalTheory]
         [InlineData("http://localhost:11001/")]
         [InlineData("invalid address")]