diff --git a/pkg/machine/wsl/machine.go b/pkg/machine/wsl/machine.go
index 20afee2dc4..38c1a91261 100644
--- a/pkg/machine/wsl/machine.go
+++ b/pkg/machine/wsl/machine.go
@@ -4,6 +4,7 @@ package wsl
 
 import (
 	"bufio"
+	"bytes"
 	"errors"
 	"fmt"
 	"io"
@@ -550,7 +551,10 @@ func runCmdPassThrough(name string, arg ...string) error {
 	cmd.Stdin = os.Stdin
 	cmd.Stdout = os.Stdout
 	cmd.Stderr = os.Stderr
-	return cmd.Run()
+	if err := cmd.Run(); err != nil {
+		return fmt.Errorf("command %s %v failed: %w", name, arg, err)
+	}
+	return nil
 }
 
 func runCmdPassThroughTee(out io.Writer, name string, arg ...string) error {
@@ -562,7 +566,10 @@ func runCmdPassThroughTee(out io.Writer, name string, arg ...string) error {
 	cmd.Stdin = os.Stdin
 	cmd.Stdout = io.MultiWriter(os.Stdout, out)
 	cmd.Stderr = io.MultiWriter(os.Stderr, out)
-	return cmd.Run()
+	if err := cmd.Run(); err != nil {
+		return fmt.Errorf("command %s %v failed: %w", name, arg, err)
+	}
+	return nil
 }
 
 func pipeCmdPassThrough(name string, input string, arg ...string) error {
@@ -571,7 +578,10 @@ func pipeCmdPassThrough(name string, input string, arg ...string) error {
 	cmd.Stdin = strings.NewReader(input)
 	cmd.Stdout = os.Stdout
 	cmd.Stderr = os.Stderr
-	return cmd.Run()
+	if err := cmd.Run(); err != nil {
+		return fmt.Errorf("command %s %v failed: %w", name, arg, err)
+	}
+	return nil
 }
 
 func setupWslProxyEnv() (hasProxy bool) {
@@ -638,8 +648,10 @@ func getAllWSLDistros(running bool) (map[string]struct{}, error) {
 	if err != nil {
 		return nil, err
 	}
+	stderr := &bytes.Buffer{}
+	cmd.Stderr = stderr
 	if err = cmd.Start(); err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to start command %s %v: %w", cmd.Path, args, err)
 	}
 
 	all := make(map[string]struct{})
@@ -651,7 +663,10 @@ func getAllWSLDistros(running bool) (map[string]struct{}, error) {
 		}
 	}
 
-	_ = cmd.Wait()
+	err = cmd.Wait()
+	if err != nil {
+		return nil, fmt.Errorf("command %s %v failed: %w (%s)", cmd.Path, args, err, strings.TrimSpace(stderr.String()))
+	}
 
 	return all, nil
 }
@@ -663,6 +678,8 @@ func isSystemdRunning(dist string) (bool, error) {
 	if err != nil {
 		return false, err
 	}
+	stderr := &bytes.Buffer{}
+	cmd.Stderr = stderr
 	if err = cmd.Start(); err != nil {
 		return false, err
 	}
@@ -676,19 +693,30 @@ func isSystemdRunning(dist string) (bool, error) {
 		}
 	}
 
-	_ = cmd.Wait()
+	err = cmd.Wait()
+	if err != nil {
+		return false, fmt.Errorf("command %s %v failed: %w (%s)", cmd.Path, cmd.Args, err, strings.TrimSpace(stderr.String()))
+	}
 
 	return result, nil
 }
 
 func terminateDist(dist string) error {
 	cmd := exec.Command(wutil.FindWSL(), "--terminate", dist)
-	return cmd.Run()
+	out, err := cmd.CombinedOutput()
+	if err != nil {
+		return fmt.Errorf("command %s %v failed: %w (%s)", cmd.Path, cmd.Args, err, strings.TrimSpace(string(out)))
+	}
+	return nil
 }
 
 func unregisterDist(dist string) error {
 	cmd := exec.Command(wutil.FindWSL(), "--unregister", dist)
-	return cmd.Run()
+	out, err := cmd.CombinedOutput()
+	if err != nil {
+		return fmt.Errorf("command %s %v failed: %w (%s)", cmd.Path, cmd.Args, err, strings.TrimSpace(string(out)))
+	}
+	return nil
 }
 
 func isRunning(name string) (bool, error) {
@@ -736,6 +764,8 @@ func getCPUs(name string) (uint64, error) {
 	if err != nil {
 		return 0, err
 	}
+	stderr := &bytes.Buffer{}
+	cmd.Stderr = stderr
 	if err = cmd.Start(); err != nil {
 		return 0, err
 	}
@@ -744,7 +774,10 @@ func getCPUs(name string) (uint64, error) {
 	for scanner.Scan() {
 		result = scanner.Text()
 	}
-	_ = cmd.Wait()
+	err = cmd.Wait()
+	if err != nil {
+		return 0, fmt.Errorf("command %s %v failed: %w (%s)", cmd.Path, cmd.Args, err, strings.TrimSpace(strings.TrimSpace(stderr.String())))
+	}
 
 	ret, err := strconv.Atoi(result)
 	return uint64(ret), err
@@ -761,6 +794,8 @@ func getMem(name string) (strongunits.MiB, error) {
 	if err != nil {
 		return 0, err
 	}
+	stderr := &bytes.Buffer{}
+	cmd.Stderr = stderr
 	if err = cmd.Start(); err != nil {
 		return 0, err
 	}
@@ -783,7 +818,10 @@ func getMem(name string) (strongunits.MiB, error) {
 			break
 		}
 	}
-	_ = cmd.Wait()
+	err = cmd.Wait()
+	if err != nil {
+		return 0, fmt.Errorf("command %s %v failed: %w (%s)", cmd.Path, cmd.Args, err, strings.TrimSpace(stderr.String()))
+	}
 
 	return strongunits.MiB(total - available), err
 }
diff --git a/pkg/machine/wsl/stubber.go b/pkg/machine/wsl/stubber.go
index 433f05eef1..3a79f095ca 100644
--- a/pkg/machine/wsl/stubber.go
+++ b/pkg/machine/wsl/stubber.go
@@ -3,6 +3,7 @@
 package wsl
 
 import (
+	"bytes"
 	"errors"
 	"fmt"
 	"os"
@@ -110,7 +111,7 @@ func (w WSLStubber) Remove(mc *vmconfigs.MachineConfig) ([]string, func() error,
 	// of the vm
 	wslRemoveFunc := func() error {
 		if err := runCmdPassThrough(wutil.FindWSL(), "--unregister", env.WithPodmanPrefix(mc.Name)); err != nil {
-			logrus.Error(err)
+			return err
 		}
 		return nil
 	}
@@ -251,17 +252,21 @@ func (w WSLStubber) StopVM(mc *vmconfigs.MachineConfig, hardStop bool) error {
 
 	cmd := exec.Command(wutil.FindWSL(), "-u", "root", "-d", dist, "sh")
 	cmd.Stdin = strings.NewReader(waitTerm)
+	out := &bytes.Buffer{}
+	cmd.Stderr = out
+	cmd.Stdout = out
+
 	if err = cmd.Start(); err != nil {
 		return fmt.Errorf("executing wait command: %w", err)
 	}
 
 	exitCmd := exec.Command(wutil.FindWSL(), "-u", "root", "-d", dist, "/usr/local/bin/enterns", "systemctl", "exit", "0")
 	if err = exitCmd.Run(); err != nil {
-		return fmt.Errorf("stopping sysd: %w", err)
+		return fmt.Errorf("stopping systemd: %w", err)
 	}
 
 	if err = cmd.Wait(); err != nil {
-		return err
+		logrus.Warnf("Failed to wait for systemd to exit: (%s)", strings.TrimSpace(out.String()))
 	}
 
 	return terminateDist(dist)
diff --git a/pkg/machine/wsl/wutil/wutil.go b/pkg/machine/wsl/wutil/wutil.go
index 3f613ab02c..bc07ffa2a9 100644
--- a/pkg/machine/wsl/wutil/wutil.go
+++ b/pkg/machine/wsl/wutil/wutil.go
@@ -4,6 +4,7 @@ package wutil
 
 import (
 	"bufio"
+	"fmt"
 	"io"
 	"os"
 	"os/exec"
@@ -74,7 +75,10 @@ func SilentExec(command string, args ...string) error {
 	cmd.SysProcAttr = &syscall.SysProcAttr{CreationFlags: 0x08000000}
 	cmd.Stdout = nil
 	cmd.Stderr = nil
-	return cmd.Run()
+	if err := cmd.Run(); err != nil {
+		return fmt.Errorf("command %s %v failed: %w", command, args, err)
+	}
+	return nil
 }
 
 func SilentExecCmd(command string, args ...string) *exec.Cmd {