diff --git a/pkg/shellexec/shellexec.go b/pkg/shellexec/shellexec.go
index d2cf64d498..6f2145827c 100644
--- a/pkg/shellexec/shellexec.go
+++ b/pkg/shellexec/shellexec.go
@@ -148,10 +148,12 @@ func (pp *PipePty) WriteString(s string) (n int, err error) {
 }
 
 func StartWslShellProc(ctx context.Context, termSize waveobj.TermSize, cmdStr string, cmdOpts CommandOptsType, conn *wsl.WslConn) (*ShellProc, error) {
+	utilCtx, cancelFn := context.WithTimeout(ctx, 2*time.Second)
+	defer cancelFn()
 	client := conn.GetClient()
 	shellPath := cmdOpts.ShellPath
 	if shellPath == "" {
-		remoteShellPath, err := wsl.DetectShell(conn.Context, client)
+		remoteShellPath, err := wsl.DetectShell(utilCtx, client)
 		if err != nil {
 			return nil, err
 		}
@@ -160,13 +162,13 @@ func StartWslShellProc(ctx context.Context, termSize waveobj.TermSize, cmdStr st
 	var shellOpts []string
 	log.Printf("detected shell: %s", shellPath)
 
-	err := wsl.InstallClientRcFiles(conn.Context, client)
+	err := wsl.InstallClientRcFiles(utilCtx, client)
 	if err != nil {
 		log.Printf("error installing rc files: %v", err)
 		return nil, err
 	}
 
-	homeDir := wsl.GetHomeDir(conn.Context, client)
+	homeDir := wsl.GetHomeDir(utilCtx, client)
 	shellOpts = append(shellOpts, "~", "-d", client.Name())
 
 	var subShellOpts []string
diff --git a/pkg/wsl/wsl.go b/pkg/wsl/wsl.go
index 673bc1a73f..4cad32bde9 100644
--- a/pkg/wsl/wsl.go
+++ b/pkg/wsl/wsl.go
@@ -51,7 +51,6 @@ type WslConn struct {
 	HasWaiter          *atomic.Bool
 	LastConnectTime    int64
 	ActiveConnNum      int
-	Context            context.Context
 	cancelFn           func()
 }
 
@@ -188,6 +187,8 @@ func (conn *WslConn) OpenDomainSocketListener() error {
 }
 
 func (conn *WslConn) StartConnServer() error {
+	utilCtx, cancelFn := context.WithTimeout(context.Background(), 5*time.Second)
+	defer cancelFn()
 	var allowed bool
 	conn.WithLock(func() {
 		if conn.Status != Status_Connecting {
@@ -200,7 +201,7 @@ func (conn *WslConn) StartConnServer() error {
 		return fmt.Errorf("cannot start conn server for %q when status is %q", conn.GetName(), conn.GetStatus())
 	}
 	client := conn.GetClient()
-	wshPath := GetWshPath(conn.Context, client)
+	wshPath := GetWshPath(utilCtx, client)
 	rpcCtx := wshrpc.RpcContext{
 		ClientType: wshrpc.ClientType_ConnServer,
 		Conn:       conn.GetName(),
@@ -210,7 +211,7 @@ func (conn *WslConn) StartConnServer() error {
 	if err != nil {
 		return fmt.Errorf("unable to create jwt token for conn controller: %w", err)
 	}
-	shellPath, err := DetectShell(conn.Context, client)
+	shellPath, err := DetectShell(utilCtx, client)
 	if err != nil {
 		return err
 	}
@@ -221,7 +222,14 @@ func (conn *WslConn) StartConnServer() error {
 		cmdStr = fmt.Sprintf("%s=\"%s\" %s connserver --router", wshutil.WaveJwtTokenVarName, jwtToken, wshPath)
 	}
 	log.Printf("starting conn controller: %s\n", cmdStr)
-	cmd := client.WslCommand(conn.Context, cmdStr)
+	connServerCtx, cancelFn := context.WithCancel(context.Background())
+	conn.WithLock(func() {
+		if conn.cancelFn != nil {
+			conn.cancelFn()
+		}
+		conn.cancelFn = cancelFn
+	})
+	cmd := client.WslCommand(connServerCtx, cmdStr)
 	pipeRead, pipeWrite := io.Pipe()
 	inputPipeRead, inputPipeWrite := io.Pipe()
 	cmd.SetStdout(pipeWrite)
@@ -473,8 +481,7 @@ func getConnInternal(name string) *WslConn {
 	connName := WslName{Distro: name}
 	rtn := clientControllerMap[name]
 	if rtn == nil {
-		ctx, cancelFn := context.WithCancel(context.Background())
-		rtn = &WslConn{Lock: &sync.Mutex{}, Status: Status_Init, Name: connName, HasWaiter: &atomic.Bool{}, Context: ctx, cancelFn: cancelFn}
+		rtn = &WslConn{Lock: &sync.Mutex{}, Status: Status_Init, Name: connName, HasWaiter: &atomic.Bool{}, cancelFn: nil}
 		clientControllerMap[name] = rtn
 	}
 	return rtn