diff --git a/CHANGELOG.md b/CHANGELOG.md
index 30043c8d..f59bf919 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@
 - Fixed spurious calls to setLastStateChangeToNow from ephemeral nodes [#566](https://github.com/juanfont/headscale/pull/566)
 - Add command for moving nodes between namespaces [#362](https://github.com/juanfont/headscale/issues/362)
 - Added more configuration parameters for OpenID Connect (scopes, free-form paramters, domain and user allowlist)
+- Add --all (-a) flag to enable routes command [#360](https://github.com/juanfont/headscale/issues/360)
 
 ## 0.15.0 (2022-03-20)
 
diff --git a/cmd/headscale/cli/routes.go b/cmd/headscale/cli/routes.go
index dc060fba..105175a1 100644
--- a/cmd/headscale/cli/routes.go
+++ b/cmd/headscale/cli/routes.go
@@ -24,6 +24,8 @@ func init() {
 	enableRouteCmd.Flags().
 		StringSliceP("route", "r", []string{}, "List (or repeated flags) of routes to enable")
 	enableRouteCmd.Flags().Uint64P("identifier", "i", 0, "Node identifier (ID)")
+	enableRouteCmd.Flags().BoolP("all", "a", false, "All routes from host")
+
 	err = enableRouteCmd.MarkFlagRequired("identifier")
 	if err != nil {
 		log.Fatalf(err.Error())
@@ -125,21 +127,43 @@ omit the route you do not want to enable.
 			return
 		}
 
-		routes, err := cmd.Flags().GetStringSlice("route")
-		if err != nil {
-			ErrorOutput(
-				err,
-				fmt.Sprintf("Error getting routes from flag: %s", err),
-				output,
-			)
-
-			return
-		}
-
 		ctx, client, conn, cancel := getHeadscaleCLIClient()
 		defer cancel()
 		defer conn.Close()
 
+		var routes []string
+
+		isAll, _ := cmd.Flags().GetBool("all")
+		if isAll {
+			response, err := client.GetMachineRoute(ctx, &v1.GetMachineRouteRequest{
+				MachineId: machineID,
+			})
+			if err != nil {
+				ErrorOutput(
+					err,
+					fmt.Sprintf(
+						"Cannot get machine routes: %s\n",
+						status.Convert(err).Message(),
+					),
+					output,
+				)
+
+				return
+			}
+			routes = response.GetRoutes().GetAdvertisedRoutes()
+		} else {
+			routes, err = cmd.Flags().GetStringSlice("route")
+			if err != nil {
+				ErrorOutput(
+					err,
+					fmt.Sprintf("Error getting routes from flag: %s", err),
+					output,
+				)
+
+				return
+			}
+		}
+
 		request := &v1.EnableMachineRoutesRequest{
 			MachineId: machineID,
 			Routes:    routes,
diff --git a/integration_cli_test.go b/integration_cli_test.go
index 29bca647..05bca29f 100644
--- a/integration_cli_test.go
+++ b/integration_cli_test.go
@@ -1076,6 +1076,35 @@ func (s *IntegrationCLITestSuite) TestRouteCommand() {
 		string(failEnableNonAdvertisedRoute),
 		"route (route-machine) is not available on node",
 	)
+
+	// Enable all routes on host
+	enableAllRouteResult, err := ExecuteCommand(
+		&s.headscale,
+		[]string{
+			"headscale",
+			"routes",
+			"enable",
+			"--output",
+			"json",
+			"--identifier",
+			"0",
+			"--all",
+		},
+		[]string{},
+	)
+	assert.Nil(s.T(), err)
+
+	var enableAllRoute v1.Routes
+	err = json.Unmarshal([]byte(enableAllRouteResult), &enableAllRoute)
+	assert.Nil(s.T(), err)
+
+	assert.Len(s.T(), enableAllRoute.AdvertisedRoutes, 2)
+	assert.Contains(s.T(), enableAllRoute.AdvertisedRoutes, "10.0.0.0/8")
+	assert.Contains(s.T(), enableAllRoute.AdvertisedRoutes, "192.168.1.0/24")
+
+	assert.Len(s.T(), enableAllRoute.EnabledRoutes, 2)
+	assert.Contains(s.T(), enableAllRoute.EnabledRoutes, "10.0.0.0/8")
+	assert.Contains(s.T(), enableAllRoute.EnabledRoutes, "192.168.1.0/24")
 }
 
 func (s *IntegrationCLITestSuite) TestApiKeyCommand() {