diff --git a/pkg/machine/hyperv/stubber.go b/pkg/machine/hyperv/stubber.go
index 97c5edb623..03838a9aee 100644
--- a/pkg/machine/hyperv/stubber.go
+++ b/pkg/machine/hyperv/stubber.go
@@ -215,8 +215,15 @@ func (h HyperVStubber) StartVM(mc *vmconfigs.MachineConfig) (func() error, func(
 		callbackFuncs.Add(rmIgnCallbackFunc)
 	}
 
+	waitReady, listener, err := mc.HyperVHypervisor.ReadyVsock.ListenSetupWait()
+	if err != nil {
+		return nil, nil, err
+	}
+
 	err = vm.Start()
 	if err != nil {
+		// cleanup the pending listener
+		_ = listener.Close()
 		return nil, nil, err
 	}
 
@@ -225,7 +232,7 @@ func (h HyperVStubber) StartVM(mc *vmconfigs.MachineConfig) (func() error, func(
 	}
 	callbackFuncs.Add(startCallback)
 
-	return nil, mc.HyperVHypervisor.ReadyVsock.Listen, err
+	return nil, waitReady, err
 }
 
 // State is returns the state as a define.status.  for hyperv, state differs from others because
diff --git a/pkg/machine/hyperv/vsock/vsock.go b/pkg/machine/hyperv/vsock/vsock.go
index 8f488e2534..202faafb38 100644
--- a/pkg/machine/hyperv/vsock/vsock.go
+++ b/pkg/machine/hyperv/vsock/vsock.go
@@ -5,6 +5,7 @@ package vsock
 import (
 	"errors"
 	"fmt"
+	"io"
 	"net"
 	"strings"
 
@@ -258,21 +259,18 @@ func (hv *HVSockRegistryEntry) Listener() (net.Listener, error) {
 	return listener, nil
 }
 
-// Listen is used on the windows side to listen for anything to come
-// over the hvsock as a signal the vm is booted
-func (hv *HVSockRegistryEntry) Listen() error {
+// ListenSetupWait creates an hvsock on the windows side and returns
+// a wait function that, when called, blocks until it receives a ready
+// notification on the vsock
+func (hv *HVSockRegistryEntry) ListenSetupWait() (func() error, io.Closer, error) {
 	listener, err := hv.Listener()
 	if err != nil {
-		return err
+		return nil, nil, err
 	}
-	defer func() {
-		if err := listener.Close(); err != nil {
-			logrus.Error(err)
-		}
-	}()
 
 	errChan := make(chan error)
 	go sockets.ListenAndWaitOnSocket(errChan, listener)
-
-	return <-errChan
+	return func() error {
+		return <-errChan
+	}, listener, nil
 }
diff --git a/pkg/machine/ignition/ready.go b/pkg/machine/ignition/ready.go
index 42a50dcfda..68bb57577b 100644
--- a/pkg/machine/ignition/ready.go
+++ b/pkg/machine/ignition/ready.go
@@ -28,7 +28,9 @@ func CreateReadyUnitFile(provider define.VMType, opts *ReadyUnitOpts) (string, e
 		if opts == nil || opts.Port == 0 {
 			return "", errors.New("no port provided for hyperv ready unit")
 		}
+		readyUnit.Add("Unit", "Requires", "sys-devices-virtual-net-vsock0.device")
 		readyUnit.Add("Unit", "After", "systemd-user-sessions.service")
+		readyUnit.Add("Unit", "After", "vsock-network.service")
 		readyUnit.Add("Service", "ExecStart", fmt.Sprintf("/bin/sh -c '/usr/bin/echo Ready | socat - VSOCK-CONNECT:2:%d'", opts.Port))
 	case define.WSLVirt: // WSL does not use ignition
 		return "", nil