diff --git a/cmd/headscale/cli/namespaces.go b/cmd/headscale/cli/namespaces.go
index 752638a7..0e5eeb4c 100644
--- a/cmd/headscale/cli/namespaces.go
+++ b/cmd/headscale/cli/namespaces.go
@@ -3,6 +3,7 @@ package cli
 import (
 	"fmt"
 
+	survey "github.com/AlecAivazis/survey/v2"
 	v1 "github.com/juanfont/headscale/gen/go/headscale/v1"
 	"github.com/pterm/pterm"
 	"github.com/rs/zerolog/log"
@@ -70,19 +71,44 @@ var destroyNamespaceCmd = &cobra.Command{
 
 		namespaceName := args[0]
 
+		request := &v1.GetNamespaceRequest{
+			Name: namespaceName,
+		}
+
 		ctx, client, conn, cancel := getHeadscaleCLIClient()
 		defer cancel()
 		defer conn.Close()
 
-		request := &v1.DeleteNamespaceRequest{Name: namespaceName}
-
-		response, err := client.DeleteNamespace(ctx, request)
+		_, err := client.GetNamespace(ctx, request)
 		if err != nil {
-			ErrorOutput(err, fmt.Sprintf("Cannot destroy namespace: %s", status.Convert(err).Message()), output)
+			ErrorOutput(err, fmt.Sprintf("Error: %s", status.Convert(err).Message()), output)
 			return
 		}
 
-		SuccessOutput(response, "Namespace destroyed", output)
+		confirm := false
+		force, _ := cmd.Flags().GetBool("force")
+		if !force {
+			prompt := &survey.Confirm{
+				Message: fmt.Sprintf("Do you want to remove the namespace '%s' and any associated preauthkeys?", namespaceName),
+			}
+			err := survey.AskOne(prompt, &confirm)
+			if err != nil {
+				return
+			}
+		}
+
+		if confirm || force {
+			request := &v1.DeleteNamespaceRequest{Name: namespaceName}
+
+			response, err := client.DeleteNamespace(ctx, request)
+			if err != nil {
+				ErrorOutput(err, fmt.Sprintf("Cannot destroy namespace: %s", status.Convert(err).Message()), output)
+				return
+			}
+			SuccessOutput(response, "Namespace destroyed", output)
+		} else {
+			SuccessOutput(map[string]string{"Result": "Namespace not destroyed"}, "Namespace not destroyed", output)
+		}
 	},
 }
 
diff --git a/namespaces.go b/namespaces.go
index 66deb1a2..e5d17839 100644
--- a/namespaces.go
+++ b/namespaces.go
@@ -15,9 +15,9 @@ import (
 )
 
 const (
-	errorNamespaceExists   = Error("Namespace already exists")
-	errorNamespaceNotFound = Error("Namespace not found")
-	errorNamespaceNotEmpty = Error("Namespace not empty")
+	errorNamespaceExists          = Error("Namespace already exists")
+	errorNamespaceNotFound        = Error("Namespace not found")
+	errorNamespaceNotEmptyOfNodes = Error("Namespace not empty: node(s) found")
 )
 
 // Namespace is the way Headscale implements the concept of users in Tailscale
@@ -60,7 +60,18 @@ func (h *Headscale) DestroyNamespace(name string) error {
 		return err
 	}
 	if len(m) > 0 {
-		return errorNamespaceNotEmpty
+		return errorNamespaceNotEmptyOfNodes
+	}
+
+	keys, err := h.ListPreAuthKeys(name)
+	if err != nil {
+		return err
+	}
+	for _, p := range keys {
+		err = h.DestroyPreAuthKey(&p)
+		if err != nil {
+			return err
+		}
 	}
 
 	if result := h.db.Unscoped().Delete(&n); result.Error != nil {
diff --git a/namespaces_test.go b/namespaces_test.go
index 7ce4850e..72193ee2 100644
--- a/namespaces_test.go
+++ b/namespaces_test.go
@@ -3,6 +3,7 @@ package headscale
 import (
 	"github.com/rs/zerolog/log"
 	"gopkg.in/check.v1"
+	"gorm.io/gorm"
 )
 
 func (s *Suite) TestCreateAndDestroyNamespace(c *check.C) {
@@ -31,6 +32,19 @@ func (s *Suite) TestDestroyNamespaceErrors(c *check.C) {
 	pak, err := h.CreatePreAuthKey(n.Name, false, false, nil)
 	c.Assert(err, check.IsNil)
 
+	err = h.DestroyNamespace("test")
+	c.Assert(err, check.IsNil)
+
+	result := h.db.Preload("Namespace").First(&pak, "key = ?", pak.Key)
+	// destroying a namespace also deletes all associated preauthkeys
+	c.Assert(result.Error, check.Equals, gorm.ErrRecordNotFound)
+
+	n, err = h.CreateNamespace("test")
+	c.Assert(err, check.IsNil)
+
+	pak, err = h.CreatePreAuthKey(n.Name, false, false, nil)
+	c.Assert(err, check.IsNil)
+
 	m := Machine{
 		ID:             0,
 		MachineKey:     "foo",
@@ -45,7 +59,7 @@ func (s *Suite) TestDestroyNamespaceErrors(c *check.C) {
 	h.db.Save(&m)
 
 	err = h.DestroyNamespace("test")
-	c.Assert(err, check.Equals, errorNamespaceNotEmpty)
+	c.Assert(err, check.Equals, errorNamespaceNotEmptyOfNodes)
 }
 
 func (s *Suite) TestRenameNamespace(c *check.C) {
diff --git a/preauth_keys.go b/preauth_keys.go
index 1cb9c112..41b10e39 100644
--- a/preauth_keys.go
+++ b/preauth_keys.go
@@ -93,6 +93,16 @@ func (h *Headscale) GetPreAuthKey(namespace string, key string) (*PreAuthKey, er
 	return pak, nil
 }
 
+// DestroyPreAuthKey destroys a preauthkey. Returns error if the PreAuthKey
+// does not exist.
+func (h *Headscale) DestroyPreAuthKey(pak *PreAuthKey) error {
+	if result := h.db.Unscoped().Delete(&pak); result.Error != nil {
+		return result.Error
+	}
+
+	return nil
+}
+
 // MarkExpirePreAuthKey marks a PreAuthKey as expired
 func (h *Headscale) ExpirePreAuthKey(k *PreAuthKey) error {
 	if err := h.db.Model(&k).Update("Expiration", time.Now()).Error; err != nil {