diff --git a/src/NATS.Server/Tls/TlsConnectionWrapper.cs b/src/NATS.Server/Tls/TlsConnectionWrapper.cs
index 5db463f..0ca0961 100644
--- a/src/NATS.Server/Tls/TlsConnectionWrapper.cs
+++ b/src/NATS.Server/Tls/TlsConnectionWrapper.cs
@@ -25,6 +25,21 @@ public static class TlsConnectionWrapper
         if (sslOptions == null || !options.HasTls)
             return (networkStream, false);
 
+        // Clone to avoid mutating shared instance
+        serverInfo = new ServerInfo
+        {
+            ServerId = serverInfo.ServerId,
+            ServerName = serverInfo.ServerName,
+            Version = serverInfo.Version,
+            Proto = serverInfo.Proto,
+            Host = serverInfo.Host,
+            Port = serverInfo.Port,
+            Headers = serverInfo.Headers,
+            MaxPayload = serverInfo.MaxPayload,
+            ClientId = serverInfo.ClientId,
+            ClientIp = serverInfo.ClientIp,
+        };
+
         // Mode 3: TLS First
         if (options.TlsHandshakeFirst)
             return await NegotiateTlsFirstAsync(socket, networkStream, options, sslOptions, serverInfo, logger, ct);
@@ -49,23 +64,30 @@ public static class TlsConnectionWrapper
         {
             // Client is starting TLS
             var sslStream = new SslStream(peekable, leaveInnerStreamOpen: false);
-            using var handshakeCts = CancellationTokenSource.CreateLinkedTokenSource(ct);
-            handshakeCts.CancelAfter(options.TlsTimeout);
-
-            await sslStream.AuthenticateAsServerAsync(sslOptions, handshakeCts.Token);
-            logger.LogDebug("TLS handshake complete: {Protocol} {CipherSuite}",
-                sslStream.SslProtocol, sslStream.NegotiatedCipherSuite);
-
-            // Validate pinned certs
-            if (options.TlsPinnedCerts != null && sslStream.RemoteCertificate is X509Certificate2 remoteCert)
+            try
             {
-                if (!TlsHelper.MatchesPinnedCert(remoteCert, options.TlsPinnedCerts))
+                using var handshakeCts = CancellationTokenSource.CreateLinkedTokenSource(ct);
+                handshakeCts.CancelAfter(options.TlsTimeout);
+
+                await sslStream.AuthenticateAsServerAsync(sslOptions, handshakeCts.Token);
+                logger.LogDebug("TLS handshake complete: {Protocol} {CipherSuite}",
+                    sslStream.SslProtocol, sslStream.NegotiatedCipherSuite);
+
+                // Validate pinned certs
+                if (options.TlsPinnedCerts != null && sslStream.RemoteCertificate is X509Certificate2 remoteCert)
                 {
-                    logger.LogWarning("Certificate pinning check failed");
-                    sslStream.Dispose();
-                    throw new InvalidOperationException("Certificate pinning check failed");
+                    if (!TlsHelper.MatchesPinnedCert(remoteCert, options.TlsPinnedCerts))
+                    {
+                        logger.LogWarning("Certificate pinning check failed");
+                        throw new InvalidOperationException("Certificate pinning check failed");
+                    }
                 }
             }
+            catch
+            {
+                sslStream.Dispose();
+                throw;
+            }
 
             return (sslStream, true);
         }
@@ -99,27 +121,35 @@ public static class TlsConnectionWrapper
         {
             // Client started TLS immediately — handshake first, then send INFO
             var sslStream = new SslStream(peekable, leaveInnerStreamOpen: false);
-            using var handshakeCts = CancellationTokenSource.CreateLinkedTokenSource(ct);
-            handshakeCts.CancelAfter(options.TlsTimeout);
-
-            await sslStream.AuthenticateAsServerAsync(sslOptions, handshakeCts.Token);
-            logger.LogDebug("TLS-first handshake complete: {Protocol} {CipherSuite}",
-                sslStream.SslProtocol, sslStream.NegotiatedCipherSuite);
-
-            // Validate pinned certs
-            if (options.TlsPinnedCerts != null && sslStream.RemoteCertificate is X509Certificate2 remoteCert)
+            try
             {
-                if (!TlsHelper.MatchesPinnedCert(remoteCert, options.TlsPinnedCerts))
+                using var handshakeCts = CancellationTokenSource.CreateLinkedTokenSource(ct);
+                handshakeCts.CancelAfter(options.TlsTimeout);
+
+                await sslStream.AuthenticateAsServerAsync(sslOptions, handshakeCts.Token);
+                logger.LogDebug("TLS-first handshake complete: {Protocol} {CipherSuite}",
+                    sslStream.SslProtocol, sslStream.NegotiatedCipherSuite);
+
+                // Validate pinned certs
+                if (options.TlsPinnedCerts != null && sslStream.RemoteCertificate is X509Certificate2 remoteCert)
                 {
-                    sslStream.Dispose();
-                    throw new InvalidOperationException("Certificate pinning check failed");
+                    if (!TlsHelper.MatchesPinnedCert(remoteCert, options.TlsPinnedCerts))
+                    {
+                        throw new InvalidOperationException("Certificate pinning check failed");
+                    }
                 }
+
+                // Now send INFO over encrypted stream
+                serverInfo.TlsRequired = true;
+                serverInfo.TlsVerify = options.TlsVerify;
+                await SendInfoAsync(sslStream, serverInfo, ct);
+            }
+            catch
+            {
+                sslStream.Dispose();
+                throw;
             }
 
-            // Now send INFO over encrypted stream
-            serverInfo.TlsRequired = true;
-            serverInfo.TlsVerify = options.TlsVerify;
-            await SendInfoAsync(sslStream, serverInfo, ct);
             return (sslStream, true);
         }
 
diff --git a/tests/NATS.Server.Tests/TlsConnectionWrapperTests.cs b/tests/NATS.Server.Tests/TlsConnectionWrapperTests.cs
index bdfc6e5..55df6cc 100644
--- a/tests/NATS.Server.Tests/TlsConnectionWrapperTests.cs
+++ b/tests/NATS.Server.Tests/TlsConnectionWrapperTests.cs
@@ -177,6 +177,58 @@ public class TlsConnectionWrapperTests
         serverNetStream.Dispose();
     }
 
+    [Fact]
+    public async Task TlsFirst_handshakes_before_sending_info()
+    {
+        var (cert, _) = TlsHelperTests.GenerateTestCert();
+
+        var (serverSocket, clientSocket) = await CreateSocketPairAsync();
+        using var clientNetStream = new NetworkStream(clientSocket, ownsSocket: true);
+
+        var opts = new NatsOptions { TlsCert = "dummy", TlsKey = "dummy", TlsHandshakeFirst = true };
+        var sslOpts = new SslServerAuthenticationOptions
+        {
+            ServerCertificate = cert,
+        };
+        var serverInfo = CreateServerInfo();
+
+        // Client side: immediately start TLS (no INFO first)
+        var clientTask = Task.Run(async () =>
+        {
+            var sslClient = new SslStream(clientNetStream, true, (_, _, _, _) => true);
+            await sslClient.AuthenticateAsClientAsync("localhost");
+
+            // After TLS, read INFO over encrypted stream
+            var buf = new byte[4096];
+            var read = await sslClient.ReadAsync(buf);
+            var info = System.Text.Encoding.ASCII.GetString(buf, 0, read);
+            info.ShouldStartWith("INFO ");
+
+            return sslClient;
+        });
+
+        var serverNetStream = new NetworkStream(serverSocket, ownsSocket: true);
+        var (stream, infoSent) = await TlsConnectionWrapper.NegotiateAsync(
+            serverSocket, serverNetStream, opts, sslOpts, serverInfo, NullLogger.Instance, CancellationToken.None);
+
+        stream.ShouldBeOfType<SslStream>();
+        infoSent.ShouldBeTrue();
+
+        var clientSsl = await clientTask;
+
+        // Verify encrypted communication works
+        await stream.WriteAsync("PING\r\n"u8.ToArray());
+        await stream.FlushAsync();
+
+        var readBuf = new byte[64];
+        var bytesRead = await clientSsl.ReadAsync(readBuf);
+        var msg = System.Text.Encoding.ASCII.GetString(readBuf, 0, bytesRead);
+        msg.ShouldBe("PING\r\n");
+
+        stream.Dispose();
+        clientSsl.Dispose();
+    }
+
     private static ServerInfo CreateServerInfo() => new()
     {
         ServerId = "TEST",