diff --git a/cio/io_windows.go b/cio/io_windows.go
index fa9532a3b..a751f7d7a 100644
--- a/cio/io_windows.go
+++ b/cio/io_windows.go
@@ -20,7 +20,6 @@ import (
 	"fmt"
 	"io"
 	"net"
-	"sync"
 
 	winio "github.com/Microsoft/go-winio"
 	"github.com/containerd/containerd/log"
@@ -41,7 +40,6 @@ func NewFIFOSetInDir(_, id string, terminal bool) (*FIFOSet, error) {
 
 func copyIO(fifos *FIFOSet, ioset *Streams) (*cio, error) {
 	var (
-		wg  sync.WaitGroup
 		set []io.Closer
 	)
 
@@ -85,9 +83,7 @@ func copyIO(fifos *FIFOSet, ioset *Streams) (*cio, error) {
 		}(l)
 		set = append(set, l)
 
-		wg.Add(1)
 		go func() {
-			defer wg.Done()
 			c, err := l.Accept()
 			if err != nil {
 				log.L.WithError(err).Errorf("failed to accept stdout connection on %s", fifos.Stdout)
@@ -115,9 +111,7 @@ func copyIO(fifos *FIFOSet, ioset *Streams) (*cio, error) {
 		}(l)
 		set = append(set, l)
 
-		wg.Add(1)
 		go func() {
-			defer wg.Done()
 			c, err := l.Accept()
 			if err != nil {
 				log.L.WithError(err).Errorf("failed to accept stderr connection on %s", fifos.Stderr)
diff --git a/cmd/ctr/commands/tasks/tasks_windows.go b/cmd/ctr/commands/tasks/tasks_windows.go
index 32dd9e4dc..5235467fc 100644
--- a/cmd/ctr/commands/tasks/tasks_windows.go
+++ b/cmd/ctr/commands/tasks/tasks_windows.go
@@ -59,15 +59,16 @@ func HandleConsoleResize(ctx gocontext.Context, task resizer, con console.Consol
 
 // NewTask creates a new task
 func NewTask(ctx gocontext.Context, client *containerd.Client, container containerd.Container, _ string, tty, nullIO bool, ioOpts []cio.Opt, opts ...containerd.NewTaskOpts) (containerd.Task, error) {
-	ioCreator := cio.NewCreator(append([]cio.Opt{cio.WithStdio}, ioOpts...)...)
+	var ioCreator cio.Creator
 	if tty {
-		ioCreator = cio.NewCreator(append([]cio.Opt{cio.WithStdio, cio.WithTerminal}, ioOpts...)...)
-	}
-	if nullIO {
-		if tty {
+		if nullIO {
 			return nil, errors.New("tty and null-io cannot be used together")
 		}
+		ioCreator = cio.NewCreator(append([]cio.Opt{cio.WithStdio, cio.WithTerminal}, ioOpts...)...)
+	} else if nullIO {
 		ioCreator = cio.NullIO
+	} else {
+		ioCreator = cio.NewCreator(append([]cio.Opt{cio.WithStdio}, ioOpts...)...)
 	}
 	return container.NewTask(ctx, ioCreator)
 }
diff --git a/runtime/v2/shim/util_windows.go b/runtime/v2/shim/util_windows.go
index 2e760ed39..be9e661ae 100644
--- a/runtime/v2/shim/util_windows.go
+++ b/runtime/v2/shim/util_windows.go
@@ -20,6 +20,7 @@ import (
 	"context"
 	"fmt"
 	"net"
+	"os"
 	"syscall"
 	"time"
 
@@ -48,7 +49,25 @@ func SocketAddress(ctx context.Context, id string) (string, error) {
 
 // AnonDialer returns a dialer for a npipe
 func AnonDialer(address string, timeout time.Duration) (net.Conn, error) {
-	return winio.DialPipe(address, &timeout)
+	var c net.Conn
+	var lastError error
+	start := time.Now()
+	for {
+		remaining := timeout - time.Now().Sub(start)
+		if remaining <= 0 {
+			lastError = errors.Errorf("timed out waiting for npipe %s", address)
+			break
+		}
+		c, lastError = winio.DialPipe(address, &remaining)
+		if lastError == nil {
+			break
+		}
+		if !os.IsNotExist(lastError) {
+			break
+		}
+		time.Sleep(10 * time.Millisecond)
+	}
+	return c, lastError
 }
 
 // NewSocket returns a new npipe listener