diff --git a/java/src/main/java/com/microsoft/tunnels/websocket/WebSocketConnector.java b/java/src/main/java/com/microsoft/tunnels/websocket/WebSocketConnector.java
index 85ddfc88..9f459912 100644
--- a/java/src/main/java/com/microsoft/tunnels/websocket/WebSocketConnector.java
+++ b/java/src/main/java/com/microsoft/tunnels/websocket/WebSocketConnector.java
@@ -19,6 +19,9 @@
 import java.net.SocketAddress;
 import java.net.URI;
 
+import javax.net.ssl.SSLEngine;
+import javax.net.ssl.SSLParameters;
+
 import org.apache.sshd.common.AttributeRepository;
 import org.apache.sshd.common.io.IoConnectFuture;
 import org.apache.sshd.common.io.IoHandler;
@@ -69,9 +72,27 @@ protected void initChannel(SocketChannel ch) throws Exception {
 
           ChannelPipeline p = ch.pipeline();
           if (factory.webSocketUri.getScheme().equals("wss")) {
-            SslContext sslContext = SslContextBuilder.forClient()
-                .trustManager(InsecureTrustManagerFactory.INSTANCE).build();
-            p.addLast("ssl", new SslHandler(sslContext.newEngine(ch.alloc())));
+            String host = factory.webSocketUri.getHost();
+            boolean isLocalDev = "localhost".equals(host)
+                || "tunnels.local.api.visualstudio.com".equals(host);
+
+            SslContextBuilder builder = SslContextBuilder.forClient();
+            if (isLocalDev) {
+              builder.trustManager(InsecureTrustManagerFactory.INSTANCE);
+            }
+            SslContext sslContext = builder.build();
+
+            var relayPort = factory.webSocketUri.getPort();
+            if (relayPort == -1) {
+              relayPort = 443;
+            }
+            SSLEngine engine = sslContext.newEngine(ch.alloc(), host, relayPort);
+            if (!isLocalDev) {
+              SSLParameters params = engine.getSSLParameters();
+              params.setEndpointIdentificationAlgorithm("HTTPS");
+              engine.setSSLParameters(params);
+            }
+            p.addLast("ssl", new SslHandler(engine));
           }
           p.addLast(new HttpClientCodec());
           p.addLast(new HttpObjectAggregator(8192));