diff --git a/config/configuration.go b/config/configuration.go
index 1425cde7b..0e220a085 100644
--- a/config/configuration.go
+++ b/config/configuration.go
@@ -843,6 +843,27 @@ const (
 	//  - Y
 	//  - N
 	SocketUseSSL string = "SocketUseSSL"
+
+	// SocketAlwaysPresentClientCertificate if set to Y, an initiator always presents its configured
+	// client certificate to the server, bypassing crypto/tls's RFC 8446 filtering against the
+	// certificate_authorities list advertised in the server's CertificateRequest.
+	//
+	// Some counterparties (e.g. stunnel servers pinning exact leaf certificates) advertise a list
+	// that does not contain the client certificate's issuer; Go would then silently send no
+	// certificate, failing the handshake, while OpenSSL-based clients send the configured
+	// certificate regardless. Setting this to Y matches the OpenSSL behavior.
+	//
+	// Only meaningful when SocketPrivateKeyFile/SocketCertificateFile (or the Bytes variants)
+	// are supplied.
+	//
+	// Required: No
+	//
+	// Default: N
+	//
+	// Valid Values:
+	//  - Y
+	//  - N
+	SocketAlwaysPresentClientCertificate string = "SocketAlwaysPresentClientCertificate"
 )
 
 const (
diff --git a/tls.go b/tls.go
index 335d8e5d7..23ff804b2 100644
--- a/tls.go
+++ b/tls.go
@@ -106,6 +106,26 @@ func loadTLSConfig(settings *SessionSettings) (*tls.Config, error) {
 		tlsConfig.Certificates[0] = certificate
 	}
 
+	if len(tlsConfig.Certificates) > 0 && settings.HasSetting(config.SocketAlwaysPresentClientCertificate) {
+		alwaysPresent, err := settings.BoolSetting(config.SocketAlwaysPresentClientCertificate)
+		if err != nil {
+			return nil, err
+		}
+
+		if alwaysPresent {
+			// As an initiator, always present the configured client certificate,
+			// bypassing the RFC 8446 acceptable-CAs filtering. Some counterparties
+			// (e.g. stunnel servers pinning exact leaf certificates) advertise a
+			// certificate_authorities list that does not contain the client cert's
+			// issuer; crypto/tls would then silently send no certificate at all,
+			// while OpenSSL-based clients send the configured cert regardless.
+			clientCert := &tlsConfig.Certificates[0]
+			tlsConfig.GetClientCertificate = func(*tls.CertificateRequestInfo) (*tls.Certificate, error) {
+				return clientCert, nil
+			}
+		}
+	}
+
 	if !allowSkipClientCerts {
 		tlsConfig.ClientAuth = tls.RequireAndVerifyClientCert
 	}
diff --git a/tls_test.go b/tls_test.go
index ea9ea93a6..86cb09a7c 100644
--- a/tls_test.go
+++ b/tls_test.go
@@ -331,3 +331,53 @@ func (s *TLSTestSuite) TestServerNameWithCertsFromBytes() {
 	s.NotNil(tlsConfig)
 	s.Equal("DummyServerNameWithCerts", tlsConfig.ServerName)
 }
+
+func (s *TLSTestSuite) TestAlwaysPresentClientCertificate() {
+	s.settings.GlobalSettings().Set(config.SocketPrivateKeyFile, s.PrivateKeyFile)
+	s.settings.GlobalSettings().Set(config.SocketCertificateFile, s.CertificateFile)
+	s.settings.GlobalSettings().Set(config.SocketAlwaysPresentClientCertificate, "Y")
+
+	tlsConfig, err := loadTLSConfig(s.settings.GlobalSettings())
+	s.Nil(err)
+	s.NotNil(tlsConfig)
+	s.Require().NotNil(tlsConfig.GetClientCertificate)
+
+	// The configured certificate is returned even when the server advertises an
+	// acceptable-CAs list that does not include the certificate's issuer.
+	cert, err := tlsConfig.GetClientCertificate(&tls.CertificateRequestInfo{
+		AcceptableCAs: [][]byte{[]byte("unrelated-ca-name")},
+	})
+	s.Nil(err)
+	s.Require().NotNil(cert)
+	s.Equal(tlsConfig.Certificates[0].Certificate, cert.Certificate)
+}
+
+func (s *TLSTestSuite) TestAlwaysPresentClientCertificateDefaultOff() {
+	s.settings.GlobalSettings().Set(config.SocketPrivateKeyFile, s.PrivateKeyFile)
+	s.settings.GlobalSettings().Set(config.SocketCertificateFile, s.CertificateFile)
+
+	tlsConfig, err := loadTLSConfig(s.settings.GlobalSettings())
+	s.Nil(err)
+	s.NotNil(tlsConfig)
+	s.Nil(tlsConfig.GetClientCertificate)
+
+	s.SetupTest()
+	s.settings.GlobalSettings().Set(config.SocketPrivateKeyFile, s.PrivateKeyFile)
+	s.settings.GlobalSettings().Set(config.SocketCertificateFile, s.CertificateFile)
+	s.settings.GlobalSettings().Set(config.SocketAlwaysPresentClientCertificate, "N")
+
+	tlsConfig, err = loadTLSConfig(s.settings.GlobalSettings())
+	s.Nil(err)
+	s.NotNil(tlsConfig)
+	s.Nil(tlsConfig.GetClientCertificate)
+}
+
+func (s *TLSTestSuite) TestAlwaysPresentClientCertificateWithoutCerts() {
+	s.settings.GlobalSettings().Set(config.SocketUseSSL, "Y")
+	s.settings.GlobalSettings().Set(config.SocketAlwaysPresentClientCertificate, "Y")
+
+	tlsConfig, err := loadTLSConfig(s.settings.GlobalSettings())
+	s.Nil(err)
+	s.NotNil(tlsConfig)
+	s.Nil(tlsConfig.GetClientCertificate)
+}