diff --git a/e2e/vm/vm_darwin_test.go b/e2e/vm/vm_darwin_test.go
index 4652cd96e..a928c5bec 100644
--- a/e2e/vm/vm_darwin_test.go
+++ b/e2e/vm/vm_darwin_test.go
@@ -96,3 +96,8 @@ var resetDisks = func(_ *option.Option, installed bool) {
 	}
 	gomega.Expect(os.RemoveAll(dataDiskDir)).ShouldNot(gomega.HaveOccurred())
 }
+
+var shutdownWSL = func() error {
+	// no-op on darwin
+	return nil
+}
diff --git a/e2e/vm/vm_test.go b/e2e/vm/vm_test.go
index 90d57b174..c7bf30ff3 100644
--- a/e2e/vm/vm_test.go
+++ b/e2e/vm/vm_test.go
@@ -4,7 +4,6 @@
 package vm
 
 import (
-	"os/exec"
 	"runtime"
 	"time"
 
@@ -29,7 +28,7 @@ var resetVM = func(o *option.Option) {
 		// clean up iptables
 		//nolint:lll // link to explanation
 		// https://docs.rancherdesktop.io/troubleshooting-tips/#q-how-do-i-fix-fata0005-subnet-1040024-overlaps-with-other-one-on-this-address-space-when-running-a-container-using-nerdctl-run
-		gomega.Expect(exec.Command("wsl", "--shutdown").Run()).Should(gomega.BeNil())
+		gomega.Expect(shutdownWSL()).Should(gomega.BeNil())
 	}
 
 	ginkgo.DeferCleanup(func() {
@@ -38,7 +37,7 @@ var resetVM = func(o *option.Option) {
 		time.Sleep(1 * time.Second)
 		command.New(o, virtualMachineRootCmd, "remove", "-f").WithoutCheckingExitCode().WithTimeoutInSeconds(10).Run()
 		if runtime.GOOS == "windows" {
-			gomega.Expect(exec.Command("wsl", "--shutdown").Run()).Should(gomega.BeNil())
+			gomega.Expect(shutdownWSL()).Should(gomega.BeNil())
 		}
 		time.Sleep(1 * time.Second)
 		command.New(o, virtualMachineRootCmd, "init").WithoutCheckingExitCode().WithTimeoutInSeconds(160).Run()
diff --git a/e2e/vm/vm_windows_test.go b/e2e/vm/vm_windows_test.go
index 2098483d5..edbc43055 100644
--- a/e2e/vm/vm_windows_test.go
+++ b/e2e/vm/vm_windows_test.go
@@ -7,9 +7,13 @@
 package vm
 
 import (
+	"context"
+	"errors"
 	"os"
+	"os/exec"
 	"path/filepath"
 	"testing"
+	"time"
 
 	"github.com/onsi/ginkgo/v2"
 	"github.com/onsi/gomega"
@@ -60,3 +64,31 @@ var resetDisks = func(_ *option.Option, _ bool) {
 	dataDiskDir := filepath.Join(finchRootDir, ".finch", ".disks")
 	gomega.Expect(os.RemoveAll(dataDiskDir)).ShouldNot(gomega.HaveOccurred())
 }
+
+// shutdownWSL is a wrapper function for "wsl --shutdown".
+//
+// This is a workaround for https://github.com/microsoft/WSL/issues/8529
+//
+// If WSL is suspected of hanging for longer than 10 seconds, then
+// kill the WSL service and retry the shutdown command.
+var shutdownWSL = func() error {
+	ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
+	defer cancel()
+
+	if err := exec.CommandContext(ctx, "wsl", "--shutdown").Run(); err != nil && errors.Is(err, context.DeadlineExceeded) {
+		// wsl is hung, kill the wsl service and try again.
+		// https://github.com/microsoft/WSL/issues/8529
+		killCtx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+		defer cancel()
+
+		exec.CommandContext(killCtx, "taskkill", "/f", "/im", "wslservice.exe").Run()
+
+		retryCtx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
+		defer cancel()
+		return exec.CommandContext(retryCtx, "wsl", "--shutdown").Run()
+	} else if err != nil {
+		return err
+	}
+
+	return nil
+}