diff --git a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/ConnectionAdapterContext.cs b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/ConnectionAdapterContext.cs
index 6d074b3a7c..1f87c8311e 100644
--- a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/ConnectionAdapterContext.cs
+++ b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/ConnectionAdapterContext.cs
@@ -2,6 +2,7 @@
 // Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
 
 using System.IO;
+using Microsoft.AspNetCore.Http.Features;
 
 namespace Microsoft.AspNetCore.Server.Kestrel.Core.Adapter.Internal
 {
@@ -9,11 +10,14 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Adapter.Internal
     // we want to add more connection metadata later.
     public class ConnectionAdapterContext
     {
-        internal ConnectionAdapterContext(Stream connectionStream)
+        internal ConnectionAdapterContext(IFeatureCollection features, Stream connectionStream)
         {
+            Features = features;
             ConnectionStream = connectionStream;
         }
 
+        public IFeatureCollection Features { get; }
+
         public Stream ConnectionStream { get; }
     }
 }
diff --git a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/IAdaptedConnection.cs b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/IAdaptedConnection.cs
index 8129cdbb35..5960490e2b 100644
--- a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/IAdaptedConnection.cs
+++ b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/IAdaptedConnection.cs
@@ -3,14 +3,11 @@
 
 using System;
 using System.IO;
-using Microsoft.AspNetCore.Http.Features;
 
 namespace Microsoft.AspNetCore.Server.Kestrel.Core.Adapter.Internal
 {
     public interface IAdaptedConnection : IDisposable
     {
         Stream ConnectionStream { get; }
-
-        void PrepareRequest(IFeatureCollection requestFeatures);
     }
 }
diff --git a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/LoggingConnectionAdapter.cs b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/LoggingConnectionAdapter.cs
index 570075ecb7..10d370df56 100644
--- a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/LoggingConnectionAdapter.cs
+++ b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Adapter/Internal/LoggingConnectionAdapter.cs
@@ -40,10 +40,6 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Adapter.Internal
 
             public Stream ConnectionStream { get; }
 
-            public void PrepareRequest(IFeatureCollection requestFeatures)
-            {
-            }
-
             public void Dispose()
             {
             }
diff --git a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Internal/FrameConnection.cs b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Internal/FrameConnection.cs
index 8ca4c36372..b9d7bcfc55 100644
--- a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Internal/FrameConnection.cs
+++ b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Internal/FrameConnection.cs
@@ -7,6 +7,7 @@ using System.Diagnostics;
 using System.IO;
 using System.Threading;
 using System.Threading.Tasks;
+using Microsoft.AspNetCore.Http.Features;
 using Microsoft.AspNetCore.Server.Kestrel.Core.Adapter.Internal;
 using Microsoft.AspNetCore.Server.Kestrel.Core.Internal.Http;
 using Microsoft.AspNetCore.Server.Kestrel.Core.Internal.Infrastructure;
@@ -20,7 +21,7 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal
     {
         private readonly FrameConnectionContext _context;
         private readonly Frame _frame;
-        private readonly List<IConnectionAdapter> _connectionAdapters;
+        private List<IAdaptedConnection> _adaptedConnections;
         private readonly TaskCompletionSource<object> _socketClosedTcs = new TaskCompletionSource<object>(TaskCreationOptions.RunContinuationsAsynchronously);
 
         private long _lastTimestamp;
@@ -33,7 +34,6 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal
         {
             _context = context;
             _frame = context.Frame;
-            _connectionAdapters = context.ConnectionAdapters;
         }
 
         public string ConnectionId => _context.ConnectionId;
@@ -78,7 +78,7 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal
                 var input = _context.Input.Reader;
                 var output = _context.Output;
 
-                if (_connectionAdapters.Count > 0)
+                if (_context.ConnectionAdapters.Count > 0)
                 {
                     adaptedPipeline = new AdaptedPipeline(input,
                                                           output,
@@ -159,17 +159,19 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal
 
         private async Task<Stream> ApplyConnectionAdaptersAsync()
         {
+            var features = new FeatureCollection();
+            var connectionAdapters = _context.ConnectionAdapters;
             var stream = new RawStream(_context.Input.Reader, _context.Output.Writer);
-            var adapterContext = new ConnectionAdapterContext(stream);
-            var adaptedConnections = new IAdaptedConnection[_connectionAdapters.Count];
+            var adapterContext = new ConnectionAdapterContext(features, stream);
+            _adaptedConnections = new List<IAdaptedConnection>(connectionAdapters.Count);
 
             try
             {
-                for (var i = 0; i < _connectionAdapters.Count; i++)
+                for (var i = 0; i < connectionAdapters.Count; i++)
                 {
-                    var adaptedConnection = await _connectionAdapters[i].OnConnectionAsync(adapterContext);
-                    adaptedConnections[i] = adaptedConnection;
-                    adapterContext = new ConnectionAdapterContext(adaptedConnection.ConnectionStream);
+                    var adaptedConnection = await connectionAdapters[i].OnConnectionAsync(adapterContext);
+                    _adaptedConnections.Add(adaptedConnection);
+                    adapterContext = new ConnectionAdapterContext(features, adaptedConnection.ConnectionStream);
                 }
             }
             catch (Exception ex)
@@ -180,7 +182,7 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal
             }
             finally
             {
-                _frame.AdaptedConnections = adaptedConnections;
+                _frame.ConnectionFeatures = features;
             }
 
             return adapterContext.ConnectionStream;
@@ -188,10 +190,10 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal
 
         private void DisposeAdaptedConnections()
         {
-            var adaptedConnections = _frame.AdaptedConnections;
+            var adaptedConnections = _adaptedConnections;
             if (adaptedConnections != null)
             {
-                for (int i = adaptedConnections.Length - 1; i >= 0; i--)
+                for (int i = adaptedConnections.Count - 1; i >= 0; i--)
                 {
                     adaptedConnections[i].Dispose();
                 }
diff --git a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Internal/Http/Frame.cs b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Internal/Http/Frame.cs
index 6a85d64757..52ea21fb96 100644
--- a/src/Microsoft.AspNetCore.Server.Kestrel.Core/Internal/Http/Frame.cs
+++ b/src/Microsoft.AspNetCore.Server.Kestrel.Core/Internal/Http/Frame.cs
@@ -12,7 +12,6 @@ using System.Text;
 using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.AspNetCore.Http;
-using Microsoft.AspNetCore.Server.Kestrel.Core.Adapter.Internal;
 using Microsoft.AspNetCore.Server.Kestrel.Core.Internal.Infrastructure;
 using Microsoft.AspNetCore.Server.Kestrel.Internal.System;
 using Microsoft.AspNetCore.Server.Kestrel.Internal.System.IO.Pipelines;
@@ -21,6 +20,7 @@ using Microsoft.AspNetCore.Server.Kestrel.Transport.Abstractions;
 using Microsoft.Extensions.Internal;
 using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Primitives;
+using Microsoft.AspNetCore.Http.Features;
 
 // ReSharper disable AccessToModifiedClosure
 
@@ -103,7 +103,7 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal.Http
 
         public IPipeReader Input { get; set; }
         public OutputProducer Output { get; set; }
-        public IAdaptedConnection[] AdaptedConnections { get; set; }
+        public IFeatureCollection ConnectionFeatures { get; set; }
         public ITimeoutControl TimeoutControl { get; set; }
 
         protected IKestrelTrace Log => ServiceContext.Log;
@@ -349,18 +349,17 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal.Http
             RequestHeaders = FrameRequestHeaders;
             ResponseHeaders = FrameResponseHeaders;
 
-            if (AdaptedConnections != null)
+            if (ConnectionFeatures != null)
             {
-                try
+                foreach (var feature in ConnectionFeatures)
                 {
-                    foreach (var adaptedConnection in AdaptedConnections)
+                    // Set the scheme to https if there's an ITlsConnectionFeature
+                    if (feature.Key == typeof(ITlsConnectionFeature))
                     {
-                        adaptedConnection.PrepareRequest(this);
+                        Scheme = "https";
                     }
-                }
-                catch (Exception ex)
-                {
-                    Log.LogError(0, ex, $"Uncaught exception from the {nameof(IAdaptedConnection.PrepareRequest)} method of an {nameof(IAdaptedConnection)}.");
+
+                    FastFeatureSet(feature.Key, feature.Value);
                 }
             }
 
diff --git a/src/Microsoft.AspNetCore.Server.Kestrel.Https/HttpsConnectionAdapter.cs b/src/Microsoft.AspNetCore.Server.Kestrel.Https/HttpsConnectionAdapter.cs
index 7c3bca81a3..328f4263aa 100644
--- a/src/Microsoft.AspNetCore.Server.Kestrel.Https/HttpsConnectionAdapter.cs
+++ b/src/Microsoft.AspNetCore.Server.Kestrel.Https/HttpsConnectionAdapter.cs
@@ -109,6 +109,12 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Https
                 return _closedAdaptedConnection;
             }
 
+            // Always set the feature even though the cert might be null
+            context.Features.Set<ITlsConnectionFeature>(new TlsConnectionFeature
+            {
+                ClientCertificate = (X509Certificate2)sslStream.RemoteCertificate
+            });
+
             return new HttpsAdaptedConnection(sslStream);
         }
 
@@ -123,17 +129,6 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Https
 
             public Stream ConnectionStream => _sslStream;
 
-            public void PrepareRequest(IFeatureCollection requestFeatures)
-            {
-                var clientCertificate = (X509Certificate2)_sslStream.RemoteCertificate;
-                if (clientCertificate != null)
-                {
-                    requestFeatures.Set<ITlsConnectionFeature>(new TlsConnectionFeature { ClientCertificate = clientCertificate });
-                }
-
-                requestFeatures.Get<IHttpRequestFeature>().Scheme = "https";
-            }
-
             public void Dispose()
             {
                 _sslStream.Dispose();
@@ -144,10 +139,6 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Https
         {
             public Stream ConnectionStream { get; } = new ClosedStream();
 
-            public void PrepareRequest(IFeatureCollection requestFeatures)
-            {
-            }
-
             public void Dispose()
             {
             }
diff --git a/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/ConnectionAdapterTests.cs b/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/ConnectionAdapterTests.cs
index eb5a857358..7c85fe99c5 100644
--- a/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/ConnectionAdapterTests.cs
+++ b/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/ConnectionAdapterTests.cs
@@ -7,7 +7,6 @@ using System.Net;
 using System.Net.Sockets;
 using System.Threading;
 using System.Threading.Tasks;
-using Microsoft.AspNetCore.Http.Features;
 using Microsoft.AspNetCore.Server.Kestrel.Core;
 using Microsoft.AspNetCore.Server.Kestrel.Core.Adapter.Internal;
 using Microsoft.AspNetCore.Testing;
@@ -218,10 +217,6 @@ namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
 
             public Stream ConnectionStream { get; }
 
-            public void PrepareRequest(IFeatureCollection requestFeatures)
-            {
-            }
-
             public void Dispose()
             {
             }
diff --git a/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/HttpsConnectionAdapterTests.cs b/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/HttpsConnectionAdapterTests.cs
index e4d6e0eb22..eb4b7976d1 100644
--- a/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/HttpsConnectionAdapterTests.cs
+++ b/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/HttpsConnectionAdapterTests.cs
@@ -94,7 +94,9 @@ namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
 
             using (var server = new TestServer(context =>
                 {
-                    Assert.Equal(context.Features.Get<ITlsConnectionFeature>(), null);
+                    var tlsFeature = context.Features.Get<ITlsConnectionFeature>();
+                    Assert.NotNull(tlsFeature);
+                    Assert.Null(tlsFeature.ClientCertificate);
                     return context.Response.WriteAsync("hello world");
                 },
                 serviceContext, listenOptions))
diff --git a/test/shared/PassThroughConnectionAdapter.cs b/test/shared/PassThroughConnectionAdapter.cs
index 7d6fdd8222..c018e49ad7 100644
--- a/test/shared/PassThroughConnectionAdapter.cs
+++ b/test/shared/PassThroughConnectionAdapter.cs
@@ -27,10 +27,6 @@ namespace Microsoft.AspNetCore.Testing
 
             public Stream ConnectionStream { get; }
 
-            public void PrepareRequest(IFeatureCollection requestFeatures)
-            {
-            }
-
             public void Dispose()
             {
             }