diff --git a/api.go b/api.go
index 9760da0d..a9711e0e 100644
--- a/api.go
+++ b/api.go
@@ -107,13 +107,14 @@ var registerWebAPITemplate = template.Must(
 `))
 
 // RegisterWebAPI shows a simple message in the browser to point to the CLI
-// Listens in /register.
+// Listens in /register/:nkey.
 func (h *Headscale) RegisterWebAPI(
 	writer http.ResponseWriter,
 	req *http.Request,
 ) {
-	nodeKeyStr := req.URL.Query().Get("key")
-	if nodeKeyStr == "" {
+	vars := mux.Vars(req)
+	nodeKeyStr, ok := vars["nkey"]
+	if !ok || nodeKeyStr == "" {
 		writer.Header().Set("Content-Type", "text/plain; charset=utf-8")
 		writer.WriteHeader(http.StatusBadRequest)
 		_, err := writer.Write([]byte("Wrong params"))
@@ -206,8 +207,6 @@ func (h *Headscale) RegistrationHandler(
 	now := time.Now().UTC()
 	machine, err := h.GetMachineByMachineKey(machineKey)
 	if errors.Is(err, gorm.ErrRecordNotFound) {
-		log.Info().Str("machine", registerRequest.Hostinfo.Hostname).Msg("New machine")
-
 		machineKeyStr := MachinePublicKeyStripPrefix(machineKey)
 
 		// If the machine has AuthKey set, handle registration via PreAuthKeys
@@ -217,6 +216,38 @@ func (h *Headscale) RegistrationHandler(
 			return
 		}
 
+		// Check if the node is waiting for interactive login
+		//
+		// TODO(juan): We could use this field to improve our protocol implementation,
+		// and hold the request until the client closes it, or the interactive
+		// login is completed (i.e., the user registers the machine).
+		// This is not implemented yet, as it is no strictly required. The only side-effect
+		// is that the client will hammer headscale with requests until it gets a
+		// successful RegisterResponse.
+		if registerRequest.Followup != "" {
+			if _, ok := h.registrationCache.Get(NodePublicKeyStripPrefix(registerRequest.NodeKey)); ok {
+				log.Debug().
+					Caller().
+					Str("machine", registerRequest.Hostinfo.Hostname).
+					Str("NodeKey", registerRequest.NodeKey.ShortString()).
+					Str("OldNodeKey", registerRequest.OldNodeKey.ShortString()).
+					Str("Followup", registerRequest.Followup).
+					Msg("Machine is waiting for interactive login")
+
+				h.handleMachineRegistrationNew(writer, req, machineKey, registerRequest)
+
+				return
+			}
+		}
+
+		log.Info().
+			Caller().
+			Str("machine", registerRequest.Hostinfo.Hostname).
+			Str("NodeKey", registerRequest.NodeKey.ShortString()).
+			Str("OldNodeKey", registerRequest.OldNodeKey.ShortString()).
+			Str("Followup", registerRequest.Followup).
+			Msg("New machine not yet in the database")
+
 		givenName, err := h.GenerateGivenName(registerRequest.Hostinfo.Hostname)
 		if err != nil {
 			log.Error().
@@ -645,7 +676,7 @@ func (h *Headscale) handleMachineRegistrationNew(
 	// The machine registration is new, redirect the client to the registration URL
 	log.Debug().
 		Str("machine", registerRequest.Hostinfo.Hostname).
-		Msg("The node is sending us a new NodeKey, sending auth url")
+		Msg("The node seems to be new, sending auth url")
 	if h.cfg.OIDC.Issuer != "" {
 		resp.AuthURL = fmt.Sprintf(
 			"%s/oidc/register/%s",
@@ -653,8 +684,8 @@ func (h *Headscale) handleMachineRegistrationNew(
 			machineKey.String(),
 		)
 	} else {
-		resp.AuthURL = fmt.Sprintf("%s/register?key=%s",
-			strings.TrimSuffix(h.cfg.ServerURL, "/"), MachinePublicKeyStripPrefix(machineKey))
+		resp.AuthURL = fmt.Sprintf("%s/register/%s",
+			strings.TrimSuffix(h.cfg.ServerURL, "/"), NodePublicKeyStripPrefix(registerRequest.NodeKey))
 	}
 
 	respBody, err := encode(resp, &machineKey, h.privateKey)
diff --git a/app.go b/app.go
index bd88dedf..60258e6e 100644
--- a/app.go
+++ b/app.go
@@ -417,7 +417,7 @@ func (h *Headscale) createRouter(grpcMux *runtime.ServeMux) *mux.Router {
 
 	router.HandleFunc("/health", h.HealthHandler).Methods(http.MethodGet)
 	router.HandleFunc("/key", h.KeyHandler).Methods(http.MethodGet)
-	router.HandleFunc("/register", h.RegisterWebAPI).Methods(http.MethodGet)
+	router.HandleFunc("/register/{nkey}", h.RegisterWebAPI).Methods(http.MethodGet)
 	router.HandleFunc("/machine/{mkey}/map", h.PollNetMapHandler).Methods(http.MethodPost)
 	router.HandleFunc("/machine/{mkey}", h.RegistrationHandler).Methods(http.MethodPost)
 	router.HandleFunc("/oidc/register/{mkey}", h.RegisterOIDC).Methods(http.MethodGet)