[HTTPS] Update certificate strategy for Mac OS

src/ProjectTemplates/test/Helpers/AspNetProcess.cs

@@ -89,8 +89,8 @@ public AspNetProcess(
         internal void EnsureDevelopmentCertificates()
         {
             var now = DateTimeOffset.Now;
-            var manager = new CertificateManager();
-            var certificate = manager.CreateAspNetCoreHttpsDevelopmentCertificate(now, now.AddYears(1), "CN=localhost");
+            var manager = CertificateManager.Instance;
+            var certificate = manager.CreateAspNetCoreHttpsDevelopmentCertificate(now, now.AddYears(1));
             manager.ExportCertificate(certificate, path: _certificatePath, includePrivateKey: true, _certificatePassword);
         }
 

src/Servers/Kestrel/Core/src/Internal/LoggerExtensions.cs

@@ -34,12 +34,28 @@ internal static class LoggerExtensions
                 new EventId(3, "FailedToLoadDevelopmentCertificate"),
                 "Failed to load the development https certificate at '{certificatePath}'.");
 
+        private static readonly Action<ILogger, Exception> _badDeveloperCertificateState =
+            LoggerMessage.Define(
+                LogLevel.Error,
+                new EventId(4, "BadDeveloperCertificateState"),
+                CoreStrings.BadDeveloperCertificateState);
+
+        private static readonly Action<ILogger, string, Exception> _developerCertificateFirstRun =
+            LoggerMessage.Define<string>(
+                LogLevel.Warning,
+                new EventId(5, "DeveloperCertificateFirstRun"),
+                "{Message}");
+
         public static void LocatedDevelopmentCertificate(this ILogger logger, X509Certificate2 certificate) => _locatedDevelopmentCertificate(logger, certificate.Subject, certificate.Thumbprint, null);
 
         public static void UnableToLocateDevelopmentCertificate(this ILogger logger) => _unableToLocateDevelopmentCertificate(logger, null);
 
         public static void FailedToLocateDevelopmentCertificateFile(this ILogger logger, string certificatePath) => _failedToLocateDevelopmentCertificateFile(logger, certificatePath, null);
 
         public static void FailedToLoadDevelopmentCertificate(this ILogger logger, string certificatePath) => _failedToLoadDevelopmentCertificate(logger, certificatePath, null);
+
+        public static void BadDeveloperCertificateState(this ILogger logger) => _badDeveloperCertificateState(logger, null);
+
+        public static void DeveloperCertificateFirstRun(this ILogger logger, string message) => _developerCertificateFirstRun(logger, message, null);
     }
 }

src/Servers/Kestrel/Core/src/KestrelServerOptions.cs

@@ -162,11 +162,29 @@ private void EnsureDefaultCert()
                 var logger = ApplicationServices.GetRequiredService<ILogger<KestrelServer>>();
                 try
                 {
-                    DefaultCertificate = CertificateManager.ListCertificates(CertificatePurpose.HTTPS, StoreName.My, StoreLocation.CurrentUser, isValid: true)
+                    DefaultCertificate = CertificateManager.Instance.ListCertificates(StoreName.My, StoreLocation.CurrentUser, isValid: true)
                         .FirstOrDefault();
 
                     if (DefaultCertificate != null)
                     {
+                        var status = CertificateManager.Instance.CheckCertificateState(DefaultCertificate, interactive: false);
+                        if (!status.Result)
+                        {
+                            // Display a warning indicating to the user that a prompt might appear and provide instructions on what to do in that
+                            // case. The underlying implementation of this check is specific to Mac OS and is handled within CheckCertificateState.
+                            // Kestrel must NEVER cause a UI prompt on a production system. We only attempt this here because Mac OS is not supported
+                            // in production.
+                            logger.DeveloperCertificateFirstRun(status.Message);
+
+                            // Now that we've displayed a warning in the logs so that the user gets a notification that a prompt might appear, try
+                            // and access the certificate key, which might trigger a prompt.
+                            status = CertificateManager.Instance.CheckCertificateState(DefaultCertificate, interactive: true);
+                            if (!status.Result)
+                            {
+                                logger.BadDeveloperCertificateState();
+                            }
+                        }
+
                         logger.LocatedDevelopmentCertificate(DefaultCertificate);
                     }
                     else

src/Servers/Kestrel/Core/src/Middleware/HttpsConnectionMiddleware.cs

@@ -220,16 +220,7 @@ public async Task OnConnectionAsync(ConnectionContext context)
                 }
                 catch (AuthenticationException ex)
                 {
-                    if (_serverCertificate == null ||
-                        !CertificateManager.IsHttpsDevelopmentCertificate(_serverCertificate) ||
-                        CertificateManager.CheckDeveloperCertificateKey(_serverCertificate))
-                    {
-                        _logger.LogDebug(1, ex, CoreStrings.AuthenticationFailed);
-                    }
-                    else
-                    {
-                        _logger.LogError(3, ex, CoreStrings.BadDeveloperCertificateState);
-                    }
+                    _logger.LogDebug(1, ex, CoreStrings.AuthenticationFailed);
 
                     await sslStream.DisposeAsync();
                     return;

src/Servers/Kestrel/test/InMemory.FunctionalTests/HttpsTests.cs

@@ -385,35 +385,6 @@ await Assert.ThrowsAnyAsync<Exception>(() =>
             Assert.Equal(LogLevel.Debug, loggerProvider.FilterLogger.LastLogLevel);
         }
 
-        [Fact]
-        public async Task DevCertWithInvalidPrivateKeyProducesCustomWarning()
-        {
-            var loggerProvider = new HandshakeErrorLoggerProvider();
-            LoggerFactory.AddProvider(loggerProvider);
-
-            await using (var server = new TestServer(context => Task.CompletedTask,
-                new TestServiceContext(LoggerFactory),
-                listenOptions =>
-                {
-                    listenOptions.UseHttps(TestResources.GetTestCertificate("aspnetdevcert.pfx", "testPassword"));
-                }))
-            {
-                using (var connection = server.CreateConnection())
-                using (var sslStream = new SslStream(connection.Stream, true, (sender, certificate, chain, errors) => true))
-                {
-                    // SslProtocols.Tls is TLS 1.0 which isn't supported by Kestrel by default.
-                    await Assert.ThrowsAnyAsync<Exception>(() =>
-                        sslStream.AuthenticateAsClientAsync("127.0.0.1", clientCertificates: null,
-                            enabledSslProtocols: SslProtocols.Tls,
-                            checkCertificateRevocation: false));
-                }
-            }
-
-            await loggerProvider.FilterLogger.LogTcs.Task.DefaultTimeout();
-            Assert.Equal(3, loggerProvider.FilterLogger.LastEventId);
-            Assert.Equal(LogLevel.Error, loggerProvider.FilterLogger.LastLogLevel);
-        }
-
         [Fact]
         public async Task OnAuthenticate_SeesOtherSettings()
         {