diff --git a/internal/codespaces/grpc/client.go b/internal/codespaces/grpc/client.go
index cf8137006..ea8399683 100644
--- a/internal/codespaces/grpc/client.go
+++ b/internal/codespaces/grpc/client.go
@@ -19,8 +19,9 @@ import (
 )
 
 const (
-	connectionTimeout = 5 * time.Second
-	requestTimeout    = 30 * time.Second
+	serverConnectionTimeout = 5 * time.Second
+	requestTimeout          = 30 * time.Second
+	portConnectionTimeout   = 30 * time.Second
 )
 
 const (
@@ -57,14 +58,17 @@ func Connect(ctx context.Context, session liveshareSession, token string) (*Clie
 	}()
 
 	// Ping the port to ensure that it is fully forwarded before continuing
-	liveshare.WaitForPortConnection(ctx, localAddress)
+	err = liveshare.WaitForPortConnection(ctx, localAddress, portConnectionTimeout)
+	if err != nil {
+		return nil, fmt.Errorf("failed to connect to local port: %w", err)
+	}
 
 	// Attempt to connect to the port
 	opts := []grpc.DialOption{
 		grpc.WithTransportCredentials(insecure.NewCredentials()),
 		grpc.WithBlock(),
 	}
-	ctx, _ = context.WithTimeout(ctx, connectionTimeout)
+	ctx, _ = context.WithTimeout(ctx, serverConnectionTimeout)
 	conn, err := grpc.DialContext(ctx, localAddress, opts...)
 	if err != nil {
 		return nil, err
diff --git a/pkg/liveshare/port_forwarder.go b/pkg/liveshare/port_forwarder.go
index 33dc6d1fa..ec23fa3d3 100644
--- a/pkg/liveshare/port_forwarder.go
+++ b/pkg/liveshare/port_forwarder.go
@@ -12,10 +12,6 @@ import (
 	"golang.org/x/sync/errgroup"
 )
 
-const (
-	connectionTimeout = 30 * time.Second
-)
-
 type portForwardingSession interface {
 	StartSharing(context.Context, string, int) (ChannelID, error)
 	OpenStreamingChannel(context.Context, ChannelID) (ssh.Channel, error)
@@ -60,12 +56,6 @@ 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
@@ -112,20 +102,17 @@ func (fwd *PortForwarder) Forward(ctx context.Context, conn io.ReadWriteCloser)
 }
 
 // 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)
+func WaitForPortConnection(ctx context.Context, address string, timeout time.Duration) error {
+	waitCtx, cancel := context.WithTimeout(ctx, timeout)
 	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:
+			default:
 				// Verify that the port can be connected to
 				conn, err := net.Dial("tcp", address)
 				if err != nil {