fix LocalCertificateSelectionCallback on unix (#63200)

* fix LocalCertificateSelectionCallback on unix

* fix linux

* use Tls12

* attempt to fix build

* fix macOS

* fix test on windows

* skip win7

* add issue reference for windows

* feedback from review

* fix space

src/libraries/Common/src/Interop/OSX/System.Security.Cryptography.Native.Apple/Interop.Ssl.cs

@@ -46,6 +46,7 @@ internal enum PAL_TlsHandshakeState
             WouldBlock,
             ServerAuthCompleted,
             ClientAuthCompleted,
+            ClientCertRequested,
         }
 
         internal enum PAL_TlsIo
@@ -99,6 +100,12 @@ private static partial int AppleCryptoNative_SslSetBreakOnClientAuth(
             int setBreak,
             out int pOSStatus);
 
+        [GeneratedDllImport(Interop.Libraries.AppleCryptoNative)]
+        private static partial int AppleCryptoNative_SslSetBreakOnCertRequested(
+            SafeSslHandle sslHandle,
+            int setBreak,
+            out int pOSStatus);
+
         [GeneratedDllImport(Interop.Libraries.AppleCryptoNative)]
         private static partial int AppleCryptoNative_SslSetCertificate(
             SafeSslHandle sslHandle,
@@ -266,6 +273,25 @@ internal static void SslBreakOnClientAuth(SafeSslHandle sslHandle, bool setBreak
             throw new SslException();
         }
 
+        internal static void SslBreakOnCertRequested(SafeSslHandle sslHandle, bool setBreak)
+        {
+            int osStatus;
+            int result = AppleCryptoNative_SslSetBreakOnCertRequested(sslHandle, setBreak ? 1 : 0, out osStatus);
+
+            if (result == 1)
+            {
+                return;
+            }
+
+            if (result == 0)
+            {
+                throw CreateExceptionForOSStatus(osStatus);
+            }
+
+            Debug.Fail($"AppleCryptoNative_SslSetBreakOnCertRequested returned {result}");
+            throw new SslException();
+        }
+
         internal static void SslSetCertificate(SafeSslHandle sslHandle, IntPtr[] certChainPtrs)
         {
             using (SafeCreateHandle cfCertRefs = CoreFoundation.CFArrayCreate(certChainPtrs, (UIntPtr)certChainPtrs.Length))

src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.OpenSsl.cs

@@ -219,6 +219,45 @@ internal static SafeSslContextHandle AllocateSslContext(SafeFreeSslCredentials c
             return sslCtx;
         }
 
+        internal static void UpdateClientCertiticate(SafeSslHandle ssl, SslAuthenticationOptions sslAuthenticationOptions)
+        {
+            // Disable certificate selection callback. We either got certificate or we will try to proceed without it.
+            Interop.Ssl.SslSetClientCertCallback(ssl, 0);
+
+            if (sslAuthenticationOptions.CertificateContext == null)
+            {
+                return;
+            }
+
+            var credential = new SafeFreeSslCredentials(sslAuthenticationOptions.CertificateContext, sslAuthenticationOptions.EnabledSslProtocols, sslAuthenticationOptions.EncryptionPolicy, sslAuthenticationOptions.IsServer);
+            SafeX509Handle? certHandle = credential.CertHandle;
+            SafeEvpPKeyHandle? certKeyHandle = credential.CertKeyHandle;
+
+            Debug.Assert(certHandle != null);
+            Debug.Assert(certKeyHandle != null);
+
+            int retVal = Ssl.SslUseCertificate(ssl, certHandle);
+            if (1 != retVal)
+            {
+                throw CreateSslException(SR.net_ssl_use_cert_failed);
+            }
+
+            retVal = Ssl.SslUsePrivateKey(ssl, certKeyHandle);
+            if (1 != retVal)
+            {
+                throw CreateSslException(SR.net_ssl_use_private_key_failed);
+            }
+
+            if (sslAuthenticationOptions.CertificateContext.IntermediateCertificates.Length > 0)
+            {
+                if (!Ssl.AddExtraChainCertificates(ssl, sslAuthenticationOptions.CertificateContext.IntermediateCertificates))
+                {
+                    throw CreateSslException(SR.net_ssl_use_cert_failed);
+                }
+            }
+
+        }
+
         // This essentially wraps SSL* SSL_new()
         internal static SafeSslHandle AllocateSslHandle(SafeFreeSslCredentials credential, SslAuthenticationOptions sslAuthenticationOptions)
         {
@@ -287,6 +326,13 @@ internal static SafeSslHandle AllocateSslHandle(SafeFreeSslCredentials credentia
                     {
                         Crypto.ErrClearError();
                     }
+
+                    if (sslAuthenticationOptions.CertSelectionDelegate != null && sslAuthenticationOptions.CertificateContext == null)
+                    {
+                        // We don't have certificate but we have callback. We should wait for remote certificate and
+                        // possible trusted issuer list.
+                        Interop.Ssl.SslSetClientCertCallback(sslHandle, 1);
+                    }
                 }
 
                 if (sslAuthenticationOptions.IsServer && sslAuthenticationOptions.RemoteCertRequired)
@@ -324,7 +370,7 @@ internal static SecurityStatusPal SslRenegotiate(SafeSslHandle sslContext, out b
             return new SecurityStatusPal(SecurityStatusPalErrorCode.OK);
         }
 
-        internal static bool DoSslHandshake(SafeSslHandle context, ReadOnlySpan<byte> input, out byte[]? sendBuf, out int sendCount)
+        internal static SecurityStatusPalErrorCode DoSslHandshake(SafeSslHandle context, ReadOnlySpan<byte> input, out byte[]? sendBuf, out int sendCount)
         {
             sendBuf = null;
             sendCount = 0;
@@ -345,6 +391,11 @@ internal static bool DoSslHandshake(SafeSslHandle context, ReadOnlySpan<byte> in
                 Exception? innerError;
                 Ssl.SslErrorCode error = GetSslError(context, retVal, out innerError);
 
+                if (error == Ssl.SslErrorCode.SSL_ERROR_WANT_X509_LOOKUP)
+                {
+                    return SecurityStatusPalErrorCode.CredentialsNeeded;
+                }
+
                 if ((retVal != -1) || (error != Ssl.SslErrorCode.SSL_ERROR_WANT_READ))
                 {
                     // Handshake failed, but even if the handshake does not need to read, there may be an Alert going out.
@@ -389,7 +440,8 @@ internal static bool DoSslHandshake(SafeSslHandle context, ReadOnlySpan<byte> in
             {
                 context.MarkHandshakeCompleted();
             }
-            return stateOk;
+
+            return stateOk ? SecurityStatusPalErrorCode.OK : SecurityStatusPalErrorCode.ContinueNeeded;
         }
 
         internal static int Encrypt(SafeSslHandle context, ReadOnlySpan<byte> input, ref byte[] output, out Ssl.SslErrorCode errorCode)

src/libraries/Common/src/Interop/Unix/System.Security.Cryptography.Native/Interop.Ssl.cs

@@ -6,6 +6,7 @@
 using System.Diagnostics;
 using System.Net.Security;
 using System.Runtime.InteropServices;
+using System.Security.Cryptography;
 using System.Security.Cryptography.X509Certificates;
 using Microsoft.Win32.SafeHandles;
 
@@ -149,6 +150,15 @@ internal static partial class Ssl
         [GeneratedDllImport(Libraries.CryptoNative, EntryPoint = "CryptoNative_SslSetData")]
         internal static partial int SslSetData(IntPtr ssl, IntPtr data);
 
+        [DllImport(Libraries.CryptoNative, EntryPoint = "CryptoNative_SslUseCertificate")]
+        internal static extern int SslUseCertificate(SafeSslHandle ssl, SafeX509Handle certPtr);
+
+        [DllImport(Libraries.CryptoNative, EntryPoint = "CryptoNative_SslUsePrivateKey")]
+        internal static extern int SslUsePrivateKey(SafeSslHandle ssl, SafeEvpPKeyHandle keyPtr);
+
+        [DllImport(Libraries.CryptoNative, EntryPoint = "CryptoNative_SslSetClientCertCallback")]
+        internal static extern unsafe void SslSetClientCertCallback(SafeSslHandle ssl, int set);
+
         [GeneratedDllImport(Libraries.CryptoNative, EntryPoint = "CryptoNative_Tls13Supported")]
         private static partial int Tls13SupportedImpl();
 
@@ -192,6 +202,28 @@ internal static byte[] ConvertAlpnProtocolListToByteArray(List<SslApplicationPro
             return buffer;
         }
 
+        [DllImport(Libraries.CryptoNative, EntryPoint = "CryptoNative_SslAddExtraChainCert")]
+        internal static extern bool SslAddExtraChainCert(SafeSslHandle ssl, SafeX509Handle x509);
+
+        internal static bool AddExtraChainCertificates(SafeSslHandle ssl, X509Certificate2[] chain)
+        {
+            // send pre-computed list of intermediates.
+            for (int i = 0; i < chain.Length; i++)
+            {
+                SafeX509Handle dupCertHandle = Crypto.X509UpRef(chain[i].Handle);
+                Crypto.CheckValidOpenSslHandle(dupCertHandle);
+                if (!SslAddExtraChainCert(ssl, dupCertHandle))
+                {
+                    Crypto.ErrClearError();
+                    dupCertHandle.Dispose(); // we still own the safe handle; clean it up
+                    return false;
+                }
+                dupCertHandle.SetHandleAsInvalid(); // ownership has been transferred to sslHandle; do not free via this safe handle
+            }
+
+            return true;
+        }
+
         internal static string? GetOpenSslCipherSuiteName(SafeSslHandle ssl, TlsCipherSuite cipherSuite, out bool isTls12OrLower)
         {
             string? ret = Marshal.PtrToStringAnsi(GetOpenSslCipherSuiteName(ssl, (int)cipherSuite, out int isTls12OrLowerInt));
@@ -224,6 +256,7 @@ internal enum SslErrorCode
             SSL_ERROR_SSL = 1,
             SSL_ERROR_WANT_READ = 2,
             SSL_ERROR_WANT_WRITE = 3,
+            SSL_ERROR_WANT_X509_LOOKUP = 4,
             SSL_ERROR_SYSCALL = 5,
             SSL_ERROR_ZERO_RETURN = 6,
 

src/libraries/System.Net.Security/src/System/Net/CertificateValidationPal.OSX.cs

@@ -128,6 +128,11 @@ internal static string[] GetRequestCertificateAuthorities(SafeDeleteContext secu
 
             using (SafeCFArrayHandle dnArray = Interop.AppleCrypto.SslCopyCADistinguishedNames(sslContext))
             {
+                if (dnArray.IsInvalid)
+                {
+                    return Array.Empty<string>();
+                }
+
                 long size = Interop.CoreFoundation.CFArrayGetCount(dnArray);
 
                 if (size == 0)

src/libraries/System.Net.Security/src/System/Net/Security/Pal.OSX/SafeDeleteSslContext.cs

@@ -316,7 +316,7 @@ private static void SetProtocols(SafeSslHandle sslContext, SslProtocols protocol
             Interop.AppleCrypto.SslSetMaxProtocolVersion(sslContext, maxProtocolId);
         }
 
-        private static void SetCertificate(SafeSslHandle sslContext, SslStreamCertificateContext context)
+        internal static void SetCertificate(SafeSslHandle sslContext, SslStreamCertificateContext context)
         {
             Debug.Assert(sslContext != null, "sslContext != null");
 

src/libraries/System.Net.Security/src/System/Net/Security/SslStreamPal.OSX.cs

@@ -246,6 +246,13 @@ private static SecurityStatusPal HandshakeInternal(
                         Interop.AppleCrypto.SslSetTargetName(sslContext.SslContext, sslAuthenticationOptions.TargetHost);
                     }
 
+                    if (sslAuthenticationOptions.CertificateContext == null && sslAuthenticationOptions.CertSelectionDelegate != null)
+                    {
+                        // certificate was not provided but there is user callback. We can break handshake if server asks for certificate
+                        // and we can try to get it based on remote certificate and trusted issuers.
+                        Interop.AppleCrypto.SslBreakOnCertRequested(sslContext.SslContext, true);
+                    }
+
                     if (sslAuthenticationOptions.IsServer && sslAuthenticationOptions.RemoteCertRequired)
                     {
                         Interop.AppleCrypto.SslSetAcceptClientCert(sslContext.SslContext);
@@ -259,6 +266,35 @@ private static SecurityStatusPal HandshakeInternal(
 
                 SafeSslHandle sslHandle = sslContext!.SslContext;
                 SecurityStatusPal status = PerformHandshake(sslHandle);
+                if (status.ErrorCode == SecurityStatusPalErrorCode.CredentialsNeeded)
+                {
+                    // we should not be here if CertSelectionDelegate is null but better check before dereferencing..
+                    if (sslAuthenticationOptions.CertSelectionDelegate != null)
+                    {
+                        X509Certificate2? remoteCert = null;
+                        try
+                        {
+                            string[] issuers = CertificateValidationPal.GetRequestCertificateAuthorities(context);
+                            remoteCert = CertificateValidationPal.GetRemoteCertificate(context);
+                            if (sslAuthenticationOptions.ClientCertificates == null)
+                            {
+                                sslAuthenticationOptions.ClientCertificates = new X509CertificateCollection();
+                            }
+                            X509Certificate2 clientCertificate = (X509Certificate2)sslAuthenticationOptions.CertSelectionDelegate(sslAuthenticationOptions.TargetHost!, sslAuthenticationOptions.ClientCertificates, remoteCert, issuers);
+                            if (clientCertificate != null)
+                            {
+                                SafeDeleteSslContext.SetCertificate(sslContext.SslContext,  SslStreamCertificateContext.Create(clientCertificate));
+                            }
+                        }
+                        finally
+                        {
+                            remoteCert?.Dispose();
+                        }
+                    }
+
+                    // We either got certificate or we can proceed without it. It is up to the server to decide if either is OK.
+                    status = PerformHandshake(sslHandle);
+                }
 
                 outputBuffer = sslContext.ReadPendingWrites();
                 return status;
@@ -290,6 +326,8 @@ private static SecurityStatusPal PerformHandshake(SafeSslHandle sslHandle)
                         // So, call SslHandshake again to indicate to Secure Transport that we've
                         // accepted this handshake and it should go into the ready state.
                         break;
+                    case PAL_TlsHandshakeState.ClientCertRequested:
+                        return new SecurityStatusPal(SecurityStatusPalErrorCode.CredentialsNeeded);
                     default:
                         return new SecurityStatusPal(
                             SecurityStatusPalErrorCode.InternalError,

src/libraries/System.Net.Security/src/System/Net/Security/SslStreamPal.Unix.cs

@@ -87,6 +87,7 @@ private static SecurityStatusPal MapNativeErrorCode(Interop.Ssl.SslErrorCode err
             {
                 Interop.Ssl.SslErrorCode.SSL_ERROR_RENEGOTIATE => new SecurityStatusPal(SecurityStatusPalErrorCode.Renegotiate),
                 Interop.Ssl.SslErrorCode.SSL_ERROR_ZERO_RETURN => new SecurityStatusPal(SecurityStatusPalErrorCode.ContextExpired),
+                Interop.Ssl.SslErrorCode.SSL_ERROR_WANT_X509_LOOKUP => new SecurityStatusPal(SecurityStatusPalErrorCode.CredentialsNeeded),
                 Interop.Ssl.SslErrorCode.SSL_ERROR_NONE or
                 Interop.Ssl.SslErrorCode.SSL_ERROR_WANT_READ => new SecurityStatusPal(SecurityStatusPalErrorCode.OK),
                 _ => new SecurityStatusPal(SecurityStatusPalErrorCode.InternalError, new Interop.OpenSsl.SslException((int)errorCode))
@@ -158,20 +159,50 @@ private static SecurityStatusPal HandshakeInternal(SafeFreeCredentials credentia
                     context = new SafeDeleteSslContext((credential as SafeFreeSslCredentials)!, sslAuthenticationOptions);
                 }
 
-                bool done = Interop.OpenSsl.DoSslHandshake(((SafeDeleteSslContext)context).SslContext, inputBuffer, out output, out outputSize);
+                SecurityStatusPalErrorCode errorCode = Interop.OpenSsl.DoSslHandshake(((SafeDeleteSslContext)context).SslContext, inputBuffer, out output, out outputSize);
+
+                if (errorCode == SecurityStatusPalErrorCode.CredentialsNeeded)
+                {
+                    if (sslAuthenticationOptions.CertSelectionDelegate != null)
+                    {
+                        X509Certificate2? remoteCert = null;
+                        string[] issuers = CertificateValidationPal.GetRequestCertificateAuthorities(context);
+                        try
+                        {
+                            remoteCert = CertificateValidationPal.GetRemoteCertificate(context);
+                            if (sslAuthenticationOptions.ClientCertificates == null)
+                            {
+                                sslAuthenticationOptions.ClientCertificates = new X509CertificateCollection();
+                            }
+                            X509Certificate2 clientCertificate = (X509Certificate2)sslAuthenticationOptions.CertSelectionDelegate(sslAuthenticationOptions.TargetHost!, sslAuthenticationOptions.ClientCertificates, remoteCert, issuers);
+                            if (clientCertificate != null && clientCertificate.HasPrivateKey)
+                            {
+                                sslAuthenticationOptions.CertificateContext = SslStreamCertificateContext.Create(clientCertificate);
+                            }
+                        }
+                        finally
+                        {
+                            remoteCert?.Dispose();
+                        }
+                    }
+
+                    Interop.OpenSsl.UpdateClientCertiticate(((SafeDeleteSslContext)context).SslContext, sslAuthenticationOptions);
+                    errorCode = Interop.OpenSsl.DoSslHandshake(((SafeDeleteSslContext)context).SslContext, null, out output, out outputSize);
+                }
+
                 // sometimes during renegotiation processing messgae does not yield new output.
                 // That seems to be flaw in OpenSSL state machine and we have workaround to peek it and try it again.
                 if (outputSize == 0 && Interop.Ssl.IsSslRenegotiatePending(((SafeDeleteSslContext)context).SslContext))
                 {
-                    done = Interop.OpenSsl.DoSslHandshake(((SafeDeleteSslContext)context).SslContext, ReadOnlySpan<byte>.Empty, out output, out outputSize);
+                    errorCode = Interop.OpenSsl.DoSslHandshake(((SafeDeleteSslContext)context).SslContext, ReadOnlySpan<byte>.Empty, out output, out outputSize);
                 }
 
                 // When the handshake is done, and the context is server, check if the alpnHandle target was set to null during ALPN.
                 // If it was, then that indicates ALPN failed, send failure.
                 // We have this workaround, as openssl supports terminating handshake only from version 1.1.0,
                 // whereas ALPN is supported from version 1.0.2.
                 SafeSslHandle sslContext = context.SslContext;
-                if (done && sslAuthenticationOptions.IsServer
+                if (errorCode == SecurityStatusPalErrorCode.OK && sslAuthenticationOptions.IsServer
                     && sslAuthenticationOptions.ApplicationProtocols != null && sslAuthenticationOptions.ApplicationProtocols.Count != 0
                     && sslContext.AlpnHandle.IsAllocated && sslContext.AlpnHandle.Target == null)
                 {
@@ -183,7 +214,7 @@ private static SecurityStatusPal HandshakeInternal(SafeFreeCredentials credentia
                     outputSize == output!.Length ? output :
                     new Span<byte>(output, 0, outputSize).ToArray();
 
-                return new SecurityStatusPal(done ? SecurityStatusPalErrorCode.OK : SecurityStatusPalErrorCode.ContinueNeeded);
+                return new SecurityStatusPal(errorCode);
             }
             catch (Exception exc)
             {