diff --git a/app.go b/app.go
index fa9b011b..139d2ed9 100644
--- a/app.go
+++ b/app.go
@@ -139,6 +139,20 @@ func (h *Headscale) expireEphemeralNodesWorker() {
 	}
 }
 
+// WatchForKVUpdates checks the KV DB table for requests to perform tailnet upgrades
+// This is a way to communitate the CLI with the headscale server
+func (h *Headscale) watchForKVUpdates(milliSeconds int64) {
+	ticker := time.NewTicker(time.Duration(milliSeconds) * time.Millisecond)
+	for range ticker.C {
+		h.watchForKVUpdatesWorker()
+	}
+}
+
+func (h *Headscale) watchForKVUpdatesWorker() {
+	h.checkForNamespacesPendingUpdates()
+	// more functions will come here in the future
+}
+
 // Serve launches a GIN server with the Headscale API
 func (h *Headscale) Serve() error {
 	r := gin.Default()
@@ -147,6 +161,9 @@ func (h *Headscale) Serve() error {
 	r.POST("/machine/:id/map", h.PollNetMapHandler)
 	r.POST("/machine/:id", h.RegistrationHandler)
 	var err error
+
+	go h.watchForKVUpdates(5000)
+
 	if h.cfg.TLSLetsEncryptHostname != "" {
 		if !strings.HasPrefix(h.cfg.ServerURL, "https://") {
 			log.Println("WARNING: listening with TLS but ServerURL does not start with https://")
diff --git a/db.go b/db.go
index 6a057e16..06302523 100644
--- a/db.go
+++ b/db.go
@@ -79,6 +79,7 @@ func (h *Headscale) openDB() (*gorm.DB, error) {
 	return db, nil
 }
 
+// getValue returns the value for the given key in KV
 func (h *Headscale) getValue(key string) (string, error) {
 	var row KV
 	if result := h.db.First(&row, "key = ?", key); errors.Is(result.Error, gorm.ErrRecordNotFound) {
@@ -87,6 +88,7 @@ func (h *Headscale) getValue(key string) (string, error) {
 	return row.Value, nil
 }
 
+// setValue sets value for the given key in KV
 func (h *Headscale) setValue(key string, value string) error {
 	kv := KV{
 		Key:   key,
diff --git a/machine.go b/machine.go
index 6f88e8d5..1895e464 100644
--- a/machine.go
+++ b/machine.go
@@ -200,19 +200,22 @@ func (h *Headscale) GetMachineByID(id uint64) (*Machine, error) {
 // DeleteMachine softs deletes a Machine from the database
 func (h *Headscale) DeleteMachine(m *Machine) error {
 	m.Registered = false
+	namespaceID := m.NamespaceID
 	h.db.Save(&m) // we mark it as unregistered, just in case
 	if err := h.db.Delete(&m).Error; err != nil {
 		return err
 	}
-	return nil
+
+	return h.RequestMapUpdates(namespaceID)
 }
 
 // HardDeleteMachine hard deletes a Machine from the database
 func (h *Headscale) HardDeleteMachine(m *Machine) error {
+	namespaceID := m.NamespaceID
 	if err := h.db.Unscoped().Delete(&m).Error; err != nil {
 		return err
 	}
-	return nil
+	return h.RequestMapUpdates(namespaceID)
 }
 
 // GetHostInfo returns a Hostinfo struct for the machine
diff --git a/machine_test.go b/machine_test.go
index 1bd29a9d..d535be56 100644
--- a/machine_test.go
+++ b/machine_test.go
@@ -1,6 +1,8 @@
 package headscale
 
 import (
+	"encoding/json"
+
 	"gopkg.in/check.v1"
 )
 
@@ -81,6 +83,15 @@ func (s *Suite) TestDeleteMachine(c *check.C) {
 	h.db.Save(&m)
 	err = h.DeleteMachine(&m)
 	c.Assert(err, check.IsNil)
+	v, err := h.getValue("namespaces_pending_updates")
+	c.Assert(err, check.IsNil)
+	names := []string{}
+	err = json.Unmarshal([]byte(v), &names)
+	c.Assert(err, check.IsNil)
+	c.Assert(names, check.DeepEquals, []string{n.Name})
+	h.checkForNamespacesPendingUpdates()
+	v, _ = h.getValue("namespaces_pending_updates")
+	c.Assert(v, check.Equals, "")
 	_, err = h.GetMachine(n.Name, "testmachine")
 	c.Assert(err, check.NotNil)
 }
diff --git a/namespaces.go b/namespaces.go
index 9897640c..c4e39e49 100644
--- a/namespaces.go
+++ b/namespaces.go
@@ -1,7 +1,9 @@
 package headscale
 
 import (
+	"encoding/json"
 	"errors"
+	"fmt"
 	"log"
 	"time"
 
@@ -103,6 +105,87 @@ func (h *Headscale) SetMachineNamespace(m *Machine, namespaceName string) error
 	return nil
 }
 
+// RequestMapUpdates signals the KV worker to update the maps for this namespace
+func (h *Headscale) RequestMapUpdates(namespaceID uint) error {
+	namespace := Namespace{}
+	if err := h.db.First(&namespace, namespaceID).Error; err != nil {
+		return err
+	}
+
+	v, err := h.getValue("namespaces_pending_updates")
+	if err != nil || v == "" {
+		err = h.setValue("namespaces_pending_updates", fmt.Sprintf(`["%s"]`, namespace.Name))
+		if err != nil {
+			return err
+		}
+		return nil
+	}
+	names := []string{}
+	err = json.Unmarshal([]byte(v), &names)
+	if err != nil {
+		err = h.setValue("namespaces_pending_updates", fmt.Sprintf(`["%s"]`, namespace.Name))
+		if err != nil {
+			return err
+		}
+		return nil
+	}
+
+	names = append(names, namespace.Name)
+	data, err := json.Marshal(names)
+	if err != nil {
+		log.Printf("Could not marshal namespaces_pending_updates: %s", err)
+		return err
+	}
+	return h.setValue("namespaces_pending_updates", string(data))
+}
+
+func (h *Headscale) checkForNamespacesPendingUpdates() {
+	v, err := h.getValue("namespaces_pending_updates")
+	if err != nil {
+		return
+	}
+	if v == "" {
+		return
+	}
+
+	names := []string{}
+	err = json.Unmarshal([]byte(v), &names)
+	if err != nil {
+		return
+	}
+	for _, name := range names {
+		machines, err := h.ListMachinesInNamespace(name)
+		if err != nil {
+			continue
+		}
+		for _, m := range *machines {
+			peers, _ := h.getPeers(m)
+			h.pollMu.Lock()
+			for _, p := range *peers {
+				pUp, ok := h.clientsPolling[uint64(p.ID)]
+				if ok {
+					log.Printf("[%s] Notifying peer %s (%s)", m.Name, p.Name, p.Addresses[0])
+					pUp <- []byte{}
+				} else {
+					log.Printf("[%s] Peer %s does not appear to be polling", m.Name, p.Name)
+				}
+			}
+			h.pollMu.Unlock()
+		}
+	}
+	newV, err := h.getValue("namespaces_pending_updates")
+	if err != nil {
+		return
+	}
+	if v == newV { // only clear when no changes, so we notified everybody
+		err = h.setValue("namespaces_pending_updates", "")
+		if err != nil {
+			log.Printf("Could not save to KV: %s", err)
+			return
+		}
+	}
+}
+
 func (n *Namespace) toUser() *tailcfg.User {
 	u := tailcfg.User{
 		ID:            tailcfg.UserID(n.ID),