diff --git a/src/Middleware/Diagnostics/src/DiagnosticsLoggerExtensions.cs b/src/Middleware/Diagnostics/src/DiagnosticsLoggerExtensions.cs
index 1a812f8d1579..210e28e768c7 100644
--- a/src/Middleware/Diagnostics/src/DiagnosticsLoggerExtensions.cs
+++ b/src/Middleware/Diagnostics/src/DiagnosticsLoggerExtensions.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;
+using Microsoft.AspNetCore.Builder;
 using Microsoft.Extensions.Logging;
 
 namespace Microsoft.AspNetCore.Diagnostics
@@ -19,9 +20,6 @@ internal static class DiagnosticsLoggerExtensions
         private static readonly Action<ILogger, Exception> _errorHandlerException =
             LoggerMessage.Define(LogLevel.Error, new EventId(3, "Exception"), "An exception was thrown attempting to execute the error handler.");
 
-        private static readonly Action<ILogger, Exception?> _errorHandlerNotFound =
-            LoggerMessage.Define(LogLevel.Warning, new EventId(4, "HandlerNotFound"), "No exception handler was found, rethrowing original exception.");
-
         // DeveloperExceptionPageMiddleware
         private static readonly Action<ILogger, Exception?> _responseStartedErrorPageMiddleware =
             LoggerMessage.Define(LogLevel.Warning, new EventId(2, "ResponseStarted"), "The response has already started, the error page middleware will not be executed.");
@@ -44,11 +42,6 @@ public static void ErrorHandlerException(this ILogger logger, Exception exceptio
             _errorHandlerException(logger, exception);
         }
 
-        public static void ErrorHandlerNotFound(this ILogger logger)
-        {
-            _errorHandlerNotFound(logger, null);
-        }
-
         public static void ResponseStartedErrorPageMiddleware(this ILogger logger)
         {
             _responseStartedErrorPageMiddleware(logger, null);
diff --git a/src/Middleware/Diagnostics/src/ExceptionHandler/ExceptionHandlerMiddleware.cs b/src/Middleware/Diagnostics/src/ExceptionHandler/ExceptionHandlerMiddleware.cs
index 11cfac7f19ce..a21a634daf11 100644
--- a/src/Middleware/Diagnostics/src/ExceptionHandler/ExceptionHandlerMiddleware.cs
+++ b/src/Middleware/Diagnostics/src/ExceptionHandler/ExceptionHandlerMiddleware.cs
@@ -142,7 +142,9 @@ private async Task HandleException(HttpContext context, ExceptionDispatchInfo ed
                     return;
                 }
 
-                _logger.ErrorHandlerNotFound();
+                edi = ExceptionDispatchInfo.Capture(new InvalidOperationException($"The exception handler configured on {nameof(ExceptionHandlerOptions)} produced a 404 status response. " +
+                    $"This {nameof(InvalidOperationException)} containing the original exception was thrown since this is often due to a misconfigured {nameof(ExceptionHandlerOptions.ExceptionHandlingPath)}. " +
+                    $"If the exception handler is expected to return 404 status responses then set {nameof(ExceptionHandlerOptions.AllowStatusCode404Response)} to true.", edi.SourceException));
             }
             catch (Exception ex2)
             {
@@ -154,7 +156,7 @@ private async Task HandleException(HttpContext context, ExceptionDispatchInfo ed
                 context.Request.Path = originalPath;
             }
 
-            edi.Throw(); // Re-throw the original if we couldn't handle it
+            edi.Throw(); // Re-throw wrapped exception or the original if we couldn't handle it
         }
 
         private static void ClearHttpContext(HttpContext context)
diff --git a/src/Middleware/Diagnostics/test/UnitTests/ExceptionHandlerTest.cs b/src/Middleware/Diagnostics/test/UnitTests/ExceptionHandlerTest.cs
index 5e2f38f7d13f..a7790bb145f6 100644
--- a/src/Middleware/Diagnostics/test/UnitTests/ExceptionHandlerTest.cs
+++ b/src/Middleware/Diagnostics/test/UnitTests/ExceptionHandlerTest.cs
@@ -469,20 +469,13 @@ public void UsingExceptionHandler_ThrowsAnException_WhenExceptionHandlingPathNot
         }
 
         [Fact]
-        public async Task ExceptionHandlerNotFound_RethrowsOriginalError()
+        public async Task ExceptionHandlerNotFound_ThrowsIOEWithOriginalError()
         {
-            var sink = new TestSink(TestSink.EnableWithTypeName<ExceptionHandlerMiddleware>);
-            var loggerFactory = new TestLoggerFactory(sink, enabled: true);
-
             using var host = new HostBuilder()
                 .ConfigureWebHost(webHostBuilder =>
                 {
                     webHostBuilder
                     .UseTestServer()
-                    .ConfigureServices(services =>
-                    {
-                        services.AddSingleton<ILoggerFactory>(loggerFactory);
-                    })
                     .Configure(app =>
                     {
                         app.Use(async (httpContext, next) =>
@@ -500,9 +493,16 @@ public async Task ExceptionHandlerNotFound_RethrowsOriginalError()
                                 httpContext.Response.StatusCode = StatusCodes.Status500InternalServerError;
                             }
 
-                            // The original exception is thrown
+                            // Invalid operation exception
                             Assert.NotNull(exception);
-                            Assert.Equal("Something bad happened.", exception.Message);
+                            Assert.Equal("The exception handler configured on ExceptionHandlerOptions produced a 404 status response. " +
+                "This InvalidOperationException containing the original exception was thrown since this is often due to a misconfigured ExceptionHandlingPath. " +
+                "If the exception handler is expected to return 404 status responses then set AllowStatusCode404Response to true.", exception.Message);
+
+                            // The original exception is inner exception
+                            Assert.NotNull(exception.InnerException);
+                            Assert.IsType<ApplicationException>(exception.InnerException);
+                            Assert.Equal("Something bad happened.", exception.InnerException.Message);
 
                         });
 
@@ -520,7 +520,7 @@ public async Task ExceptionHandlerNotFound_RethrowsOriginalError()
                         {
                             innerAppBuilder.Run(httpContext =>
                             {
-                                throw new InvalidOperationException("Something bad happened.");
+                                throw new ApplicationException("Something bad happened.");
                             });
                         });
                     });
@@ -535,11 +535,6 @@ public async Task ExceptionHandlerNotFound_RethrowsOriginalError()
                 Assert.Equal(HttpStatusCode.InternalServerError, response.StatusCode);
                 Assert.Equal(string.Empty, await response.Content.ReadAsStringAsync());
             }
-
-            Assert.Contains(sink.Writes, w =>
-                w.LogLevel == LogLevel.Warning
-                && w.EventId == 4
-                && w.Message == "No exception handler was found, rethrowing original exception.");
         }
 
         [Fact]