diff --git a/src/Microsoft.AspNetCore.Routing/EndpointRoutingMiddleware.cs b/src/Microsoft.AspNetCore.Routing/EndpointRoutingMiddleware.cs
index 0b82dc3438..60efa46586 100644
--- a/src/Microsoft.AspNetCore.Routing/EndpointRoutingMiddleware.cs
+++ b/src/Microsoft.AspNetCore.Routing/EndpointRoutingMiddleware.cs
@@ -95,23 +95,51 @@ namespace Microsoft.AspNetCore.Routing
         // blocking operation if you have a low core count and enough work to do.
         private Task<Matcher> InitializeAsync()
         {
-            if (_initializationTask != null)
+            var initializationTask = _initializationTask;
+            if (initializationTask != null)
             {
-                return _initializationTask;
+                return initializationTask;
             }
 
-            var initializationTask = new TaskCompletionSource<Matcher>();
-            if (Interlocked.CompareExchange<Task<Matcher>>(
-                ref _initializationTask,
-                initializationTask.Task,
-                null) == null)
+            return InitializeCoreAsync();
+        }
+
+        private Task<Matcher> InitializeCoreAsync()
+        {
+            var initialization = new TaskCompletionSource<Matcher>(TaskCreationOptions.RunContinuationsAsynchronously);
+            var initializationTask = Interlocked.CompareExchange(ref _initializationTask, initialization.Task, null);
+            if (initializationTask != null)
+            {
+                // This thread lost the race, join the existing task.
+                return initializationTask;
+            }
+
+            // This thread won the race, do the initialization.
+            try
             {
-                // This thread won the race, do the initialization.
                 var matcher = _matcherFactory.CreateMatcher(_endpointDataSource);
-                initializationTask.SetResult(matcher);
-            }
 
-            return _initializationTask;
+                // Now replace the initialization task with one created with the default execution context.
+                // This is important because capturing the execution context will leak memory in ASP.NET Core.
+                using (ExecutionContext.SuppressFlow())
+                {
+                    _initializationTask = Task.FromResult(matcher);
+                }
+
+                // Complete the task, this will unblock any requests that came in while initializing.
+                initialization.SetResult(matcher);
+                return initialization.Task;
+            }
+            catch (Exception ex)
+            {
+                // Allow initialization to occur again. Since DataSources can change, it's possible
+                // for the developer to correct the data causing the failure.
+                _initializationTask = null;
+
+                // Complete the task, this will throw for any requests that came in while initializing.
+                initialization.SetException(ex);
+                return initialization.Task;
+            }
         }
 
         private static class Log
diff --git a/test/Microsoft.AspNetCore.Routing.Tests/EndpointRoutingMiddlewareTest.cs b/test/Microsoft.AspNetCore.Routing.Tests/EndpointRoutingMiddlewareTest.cs
index dad2fdf0ff..48861da09b 100644
--- a/test/Microsoft.AspNetCore.Routing.Tests/EndpointRoutingMiddlewareTest.cs
+++ b/test/Microsoft.AspNetCore.Routing.Tests/EndpointRoutingMiddlewareTest.cs
@@ -2,14 +2,17 @@
 // Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
 
 using System;
+using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.AspNetCore.Http;
 using Microsoft.AspNetCore.Http.Features;
+using Microsoft.AspNetCore.Routing.Matching;
 using Microsoft.AspNetCore.Routing.TestObjects;
 using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Logging.Abstractions;
 using Microsoft.Extensions.Logging.Testing;
 using Microsoft.Extensions.Options;
+using Moq;
 using Xunit;
 
 namespace Microsoft.AspNetCore.Routing
@@ -103,6 +106,29 @@ namespace Microsoft.AspNetCore.Routing
             Assert.Equal("testValue", routeValuesFeature.RouteValues["testKey"]);
         }
 
+        [Fact]
+        public async Task Invoke_InitializationFailure_AllowsReinitialization()
+        {
+            // Arrange
+            var httpContext = CreateHttpContext();
+
+            var matcherFactory = new Mock<MatcherFactory>();
+            matcherFactory
+                .Setup(f => f.CreateMatcher(It.IsAny<EndpointDataSource>()))
+                .Throws(new InvalidTimeZoneException())
+                .Verifiable();
+
+            var middleware = CreateMiddleware(matcherFactory: matcherFactory.Object);
+
+            // Act
+            await Assert.ThrowsAsync<InvalidTimeZoneException>(async () => await middleware.Invoke(httpContext));
+            await Assert.ThrowsAsync<InvalidTimeZoneException>(async () => await middleware.Invoke(httpContext));
+
+            // Assert
+            matcherFactory
+                .Verify(f => f.CreateMatcher(It.IsAny<EndpointDataSource>()), Times.Exactly(2));
+        }
+
         private HttpContext CreateHttpContext()
         {
             var context = new EndpointSelectorContext();
@@ -116,14 +142,16 @@ namespace Microsoft.AspNetCore.Routing
             return httpContext;
         }
 
-        private EndpointRoutingMiddleware CreateMiddleware(Logger<EndpointRoutingMiddleware> logger = null)
+        private EndpointRoutingMiddleware CreateMiddleware(
+            Logger<EndpointRoutingMiddleware> logger = null,
+            MatcherFactory matcherFactory = null)
         {
             RequestDelegate next = (c) => Task.FromResult<object>(null);
 
             logger = logger ?? new Logger<EndpointRoutingMiddleware>(NullLoggerFactory.Instance);
+            matcherFactory = matcherFactory ?? new TestMatcherFactory(true);
 
             var options = Options.Create(new EndpointOptions());
-            var matcherFactory = new TestMatcherFactory(true);
             var middleware = new EndpointRoutingMiddleware(
                 matcherFactory,
                 new CompositeEndpointDataSource(Array.Empty<EndpointDataSource>()),