diff --git a/internal/codespaces/grpc/client.go b/internal/codespaces/grpc/client.go
index 7ceeac7d1..cf8137006 100644
--- a/internal/codespaces/grpc/client.go
+++ b/internal/codespaces/grpc/client.go
@@ -49,14 +49,15 @@ func Connect(ctx context.Context, session liveshareSession, token string) (*Clie
 	}
 
 	// Tunnel the remote gRPC server port to the local port
-	localPort := listener.Addr().(*net.TCPAddr).Port
+	localAddress := fmt.Sprintf("127.0.0.1:%d", listener.Addr().(*net.TCPAddr).Port)
 	internalTunnelClosed := make(chan error, 1)
 	go func() {
 		fwd := liveshare.NewPortForwarder(session, codespacesInternalSessionName, codespacesInternalPort, true)
 		internalTunnelClosed <- fwd.ForwardToListener(ctx, listener)
 	}()
 
-	time.Sleep(time.Millisecond)
+	// Ping the port to ensure that it is fully forwarded before continuing
+	liveshare.WaitForPortConnection(ctx, localAddress)
 
 	// Attempt to connect to the port
 	opts := []grpc.DialOption{
@@ -64,7 +65,7 @@ func Connect(ctx context.Context, session liveshareSession, token string) (*Clie
 		grpc.WithBlock(),
 	}
 	ctx, _ = context.WithTimeout(ctx, connectionTimeout)
-	conn, err := grpc.DialContext(ctx, fmt.Sprintf("127.0.0.1:%d", localPort), opts...)
+	conn, err := grpc.DialContext(ctx, localAddress, opts...)
 	if err != nil {
 		return nil, err
 	}
diff --git a/internal/codespaces/grpc/test/session.go b/internal/codespaces/grpc/test/session.go
index e29027dc6..ec4d69649 100644
--- a/internal/codespaces/grpc/test/session.go
+++ b/internal/codespaces/grpc/test/session.go
@@ -21,6 +21,7 @@ func (s *Session) StartSharing(ctx context.Context, sessionName string, port int
 	return liveshare.ChannelID{}, nil
 }
 
+// Creates mock SSH channel connected to the mock gRPC server
 func (s *Session) OpenStreamingChannel(ctx context.Context, id liveshare.ChannelID) (ssh.Channel, error) {
 	dialer := net.Dialer{}
 	conn, err := dialer.Dial("tcp", fmt.Sprintf("127.0.0.1:%d", ServerPort))
diff --git a/pkg/liveshare/port_forwarder.go b/pkg/liveshare/port_forwarder.go
index f042eeaea..33dc6d1fa 100644
--- a/pkg/liveshare/port_forwarder.go
+++ b/pkg/liveshare/port_forwarder.go
@@ -5,9 +5,15 @@ import (
 	"fmt"
 	"io"
 	"net"
+	"time"
 
 	"github.com/opentracing/opentracing-go"
 	"golang.org/x/crypto/ssh"
+	"golang.org/x/sync/errgroup"
+)
+
+const (
+	connectionTimeout = 30 * time.Second
 )
 
 type portForwardingSession interface {
@@ -54,6 +60,12 @@ func (fwd *PortForwarder) ForwardToListener(ctx context.Context, listen net.List
 		return err
 	}
 
+	// Ping the port to ensure that it is fully forwarded before continuing
+	err = WaitForPortConnection(ctx, listen.Addr().String())
+	if err != nil {
+		return err
+	}
+
 	errc := make(chan error, 1)
 	sendError := func(err error) {
 		// Use non-blocking send, to avoid goroutines getting
@@ -99,6 +111,43 @@ func (fwd *PortForwarder) Forward(ctx context.Context, conn io.ReadWriteCloser)
 	return awaitError(ctx, errc)
 }
 
+// Connects to and pings a given address to ensure that the server is shared and the port is forwarded.
+func WaitForPortConnection(ctx context.Context, address string) error {
+	waitCtx, cancel := context.WithTimeout(ctx, connectionTimeout)
+	g, waitCtx := errgroup.WithContext(waitCtx)
+	defer cancel()
+
+	ticker := time.NewTicker(1 * time.Second)
+	defer ticker.Stop()
+
+	g.Go(func() error {
+		for {
+			select {
+			case <-waitCtx.Done():
+				return fmt.Errorf("timed out waiting for connection")
+			case <-ticker.C:
+				// Verify that the port can be connected to
+				conn, err := net.Dial("tcp", address)
+				if err != nil {
+					continue
+				}
+
+				defer conn.Close()
+
+				// Send a ping and make sure it succeed
+				_, err = conn.Write([]byte("ping"))
+				if err != nil {
+					continue
+				}
+
+				return nil
+			}
+		}
+	})
+
+	return g.Wait()
+}
+
 func (fwd *PortForwarder) shareRemotePort(ctx context.Context) (ChannelID, error) {
 	id, err := fwd.session.StartSharing(ctx, fwd.name, fwd.remotePort)
 	if err != nil {