diff --git a/app/app.go b/app/app.go
index b139319b2..1f0dd9343 100644
--- a/app/app.go
+++ b/app/app.go
@@ -11,6 +11,7 @@ import (
 	"sync"
 	"time"
 
+	"github.com/pkg/errors"
 	"github.com/wailsapp/wails/v2/pkg/mac"
 
 	"github.com/gregjones/httpcache"
@@ -27,6 +28,7 @@ import (
 var (
 	pluginDirectory = filepath.Join(os.Getenv("HOME"), "Library", "Application Support", "xbar", "plugins")
 	cacheDirectory  = filepath.Join(os.Getenv("HOME"), "Library", "Application Support", "xbar", "cache")
+	configFilename  = filepath.Join(os.Getenv("HOME"), "Library", "Application Support", "xbar", "xbar.config.json")
 
 	// concurrentIncomingURLs is the number of concurrent incoming URLs to handle at
 	// the same time.
@@ -39,6 +41,8 @@ var (
 type app struct {
 	runtime *wails.Runtime
 
+	settings *settings
+
 	// appMenu isn't visible - it's used for key shortcuts.
 	appMenu           *menu.Menu
 	contextMenus      []*menu.ContextMenu
@@ -47,6 +51,7 @@ type app struct {
 	pluginTrays       map[string]*menu.TrayMenu
 	menuParser        *MenuParser
 	startsAtLoginMenu *menu.MenuItem
+	autoupdateMenu    *menu.MenuItem
 	appUpdatesMenu    *menu.MenuItem
 
 	// Verbose gets whether verbose output will be printed
@@ -80,8 +85,13 @@ type app struct {
 }
 
 // newApp makes a new app.
-func newApp() *app {
+func newApp() (*app, error) {
+	settings, err := loadSettings(configFilename)
+	if err != nil {
+		return nil, errors.Wrap(err, "loadSettings")
+	}
 	app := &app{
+		settings:             settings,
 		Verbose:              true,
 		menuParser:           NewMenuParser(),
 		incomingURLSemaphore: make(chan struct{}, concurrentIncomingURLs),
@@ -113,6 +123,13 @@ func newApp() *app {
 		Click: app.onCheckForUpdatesMenuClick,
 	}
 
+	app.autoupdateMenu = &menu.MenuItem{
+		Label:   "Update automatically",
+		Type:    menu.CheckboxType,
+		Checked: app.settings.AutoUpdate,
+		Click:   app.updateAutoupdate,
+	}
+
 	app.startsAtLoginMenu = &menu.MenuItem{
 		Label:   "Start at Login",
 		Type:    menu.CheckboxType,
@@ -145,7 +162,7 @@ func newApp() *app {
 		Label: "xbar",
 		Menu:  app.newXbarMenu(nil, false),
 	}
-	return app
+	return app, nil
 }
 
 func (app *app) Start(runtime *wails.Runtime) {
@@ -168,7 +185,11 @@ func (app *app) Start(runtime *wails.Runtime) {
 	go func() {
 		// wait before checking for updates
 		time.Sleep(10 * time.Second)
-		app.checkForUpdates(true)
+		for {
+			app.checkForUpdates(true)
+			// check again in twelve hours
+			time.Sleep(12 * time.Hour)
+		}
 	}()
 }
 
@@ -263,6 +284,28 @@ func (app *app) updateStartOnLogin(data *menu.CallbackData) {
 	app.refreshMenus()
 }
 
+func (app *app) updateAutoupdate(data *menu.CallbackData) {
+	if data.MenuItem.Checked && app.settings.AutoUpdate {
+		// nothing to do
+		return
+	}
+	if !data.MenuItem.Checked && !app.settings.AutoUpdate {
+		// nothing to do
+		return
+	}
+	app.settings.AutoUpdate = data.MenuItem.Checked
+	if err := app.settings.save(); err != nil {
+		log.Println("err: updateAutoupdate:", err)
+		return
+	}
+	if app.settings.AutoUpdate {
+		go app.checkForUpdates(true)
+	}
+	// We need to refresh all as the menuitem is used in multiple places.
+	// If we don't refresh, only the menuitem clicked will toggle in the UI.
+	app.refreshMenus()
+}
+
 // onErr adds a single menu showing the specified error
 // string.
 func (app *app) onErr(err string) {
@@ -346,6 +389,7 @@ func (app *app) newXbarMenu(plugin *plugins.Plugin, asSubmenu bool) *menu.Menu {
 		Disabled: true,
 	})
 	items = append(items, app.appUpdatesMenu)
+	items = append(items, app.autoupdateMenu)
 	items = append(items, app.startsAtLoginMenu)
 	items = append(items, menu.Separator())
 	items = append(items, &menu.MenuItem{
@@ -561,6 +605,11 @@ func (app *app) updateLabel(tray *menu.TrayMenu, p *plugins.Plugin) bool {
 // downloads it and installs it.
 // If passive is true, it won't complain if it fails.
 func (app *app) checkForUpdates(passive bool) {
+	if app.Verbose {
+		log.Printf("checking for updates... (current: %s)", version)
+		log.Println("updates: passive", passive)
+		log.Println("updates: AutoUpdate", app.settings.AutoUpdate)
+	}
 	u := update.Updater{
 		CurrentVersion: version,
 		//LatestReleaseGitHubEndpoint: "https://api.github.com/repos/matryer/xbar/releases/latest",
@@ -574,7 +623,9 @@ func (app *app) checkForUpdates(passive bool) {
 	}
 	latest, hasUpdate, err := u.HasUpdate()
 	if err != nil {
-		log.Println("failed to check for updates:", err)
+		if app.Verbose {
+			log.Println("failed to check for updates:", err)
+		}
 		if !passive {
 			app.runtime.Dialog.Message(&dialog.MessageDialog{
 				Type:         dialog.ErrorDialog,
@@ -588,6 +639,9 @@ func (app *app) checkForUpdates(passive bool) {
 	}
 	if !hasUpdate {
 		// they are using the latest version
+		if app.Verbose {
+			log.Println("update: you have the latest version")
+		}
 		if !passive {
 			app.runtime.Dialog.Message(&dialog.MessageDialog{
 				Type:         dialog.InfoDialog,
@@ -599,49 +653,64 @@ func (app *app) checkForUpdates(passive bool) {
 		}
 		return
 	}
-	oneWeek := 168 * time.Hour
-	// if this check is passive, and the release is only a few days
-	// old - do a soft prompt.
-	if passive && latest.CreatedAt.After(time.Now().Add(0-oneWeek)) {
-		// Update menu text
-		app.appUpdatesMenu.Label = "Install " + latest.TagName + "…"
-		app.refreshMenus()
-		return
-	}
-	switch app.runtime.Dialog.Message(&dialog.MessageDialog{
-		Type:          dialog.QuestionDialog,
-		Title:         "Update xbar?",
-		Message:       fmt.Sprintf("xbar %s is now available (you have %s).\n\nWould you like to update?", latest.TagName, u.CurrentVersion),
-		Buttons:       []string{"Update", "Later"},
-		DefaultButton: "Update",
-		CancelButton:  "Later",
-	}) {
-	case "Update":
-		// continue
-	case "Later":
-		return
+	if !app.settings.AutoUpdate {
+		oneWeek := 168 * time.Hour
+		// if this check is passive, and the release is only a few days
+		// old - do a soft prompt.
+		if passive && latest.CreatedAt.After(time.Now().Add(0-oneWeek)) {
+			// Update menu text
+			app.appUpdatesMenu.Label = "Install " + latest.TagName + "…"
+			app.refreshMenus()
+			return
+		}
+		switch app.runtime.Dialog.Message(&dialog.MessageDialog{
+			Type:          dialog.QuestionDialog,
+			Title:         "Update xbar?",
+			Message:       fmt.Sprintf("xbar %s is now available (you have %s).\n\nWould you like to update?", latest.TagName, u.CurrentVersion),
+			Buttons:       []string{"Update", "Later"},
+			DefaultButton: "Update",
+			CancelButton:  "Later",
+		}) {
+		case "Update":
+			// continue
+		case "Later":
+			return
+		}
+	} else {
+		if app.Verbose {
+			log.Println("autoupdating...")
+		}
 	}
 	_, err = u.Update()
 	if err != nil {
-		app.runtime.Dialog.Message(&dialog.MessageDialog{
-			Type:         dialog.ErrorDialog,
-			Title:        "Update failed",
-			Message:      err.Error(),
-			Buttons:      []string{"OK"},
-			CancelButton: "OK",
-		})
+		if app.Verbose {
+			log.Println("failed to update:", err)
+		}
+		if !passive {
+			app.runtime.Dialog.Message(&dialog.MessageDialog{
+				Type:         dialog.InfoDialog,
+				Title:        "Update successful",
+				Message:      "Please restart xbar for the changes to take effect.",
+				Buttons:      []string{"OK"},
+				CancelButton: "OK",
+			})
+		}
 		return
 	}
 	err = u.Restart()
 	if err != nil {
-		log.Println("failed to restart:", err)
-		app.runtime.Dialog.Message(&dialog.MessageDialog{
-			Type:         dialog.InfoDialog,
-			Title:        "Update successful",
-			Message:      "Please restart xbar for the changes to take effect.",
-			Buttons:      []string{"OK"},
-			CancelButton: "OK",
-		})
+		if app.Verbose {
+			log.Println("failed to restart:", err)
+		}
+		if !passive {
+			app.runtime.Dialog.Message(&dialog.MessageDialog{
+				Type:         dialog.InfoDialog,
+				Title:        "Update successful",
+				Message:      "Please restart xbar for the changes to take effect.",
+				Buttons:      []string{"OK"},
+				CancelButton: "OK",
+			})
+		}
 		return
 	}
 }
diff --git a/app/go.mod b/app/go.mod
index 6bbea082c..4b58ce57a 100644
--- a/app/go.mod
+++ b/app/go.mod
@@ -12,7 +12,7 @@ require (
 	github.com/matryer/xbar/pkg/update v0.0.0-00010101000000-000000000000
 	github.com/peterbourgon/diskv v2.0.1+incompatible // indirect
 	github.com/pkg/errors v0.9.1
-	github.com/wailsapp/wails/v2 v2.0.0-alpha.60
+	github.com/wailsapp/wails/v2 v2.0.0-alpha.62
 	golang.org/x/sys v0.0.0-20201207223542-d4d67f95c62d // indirect
 )
 
diff --git a/app/go.sum b/app/go.sum
index 6e7f03858..1c26c7055 100644
--- a/app/go.sum
+++ b/app/go.sum
@@ -99,8 +99,8 @@ github.com/ugorji/go/codec v1.1.7/go.mod h1:Ax+UKWsSmolVDwsd+7N3ZtXu+yMGCf907BLY
 github.com/ulikunitz/xz v0.5.6/go.mod h1:2bypXElzHzzJZwzH67Y6wb67pO62Rzfn7BSiF4ABRW8=
 github.com/ulikunitz/xz v0.5.10 h1:t92gobL9l3HE202wg3rlk19F6X+JOxl9BBrCCMYEYd8=
 github.com/ulikunitz/xz v0.5.10/go.mod h1:nbz6k7qbPmH4IRqmfOplQw/tblSgqTqBwxkY0oWt/14=
-github.com/wailsapp/wails/v2 v2.0.0-alpha.60 h1:ji3co6B6n0y3Hd0h+fAH8bvE1TPRl7sEQE+Zj89Qr7g=
-github.com/wailsapp/wails/v2 v2.0.0-alpha.60/go.mod h1:Yc65JRHZwCwYfBTaemkOzN7nOl2e1iBVZMzEVPxsQ9s=
+github.com/wailsapp/wails/v2 v2.0.0-alpha.62 h1:MtcgSY4vVj/Al/wMpyEJZXI2xOGBXGNpH47JSABgRts=
+github.com/wailsapp/wails/v2 v2.0.0-alpha.62/go.mod h1:Yc65JRHZwCwYfBTaemkOzN7nOl2e1iBVZMzEVPxsQ9s=
 github.com/wzshiming/ctc v1.2.3/go.mod h1:2tVAtIY7SUyraSk0JxvwmONNPFL4ARavPuEsg5+KA28=
 github.com/wzshiming/winseq v0.0.0-20200112104235-db357dc107ae/go.mod h1:VTAq37rkGeV+WOybvZwjXiJOicICdpLCN8ifpISjK20=
 github.com/xi2/xz v0.0.0-20171230120015-48954b6210f8 h1:nIPpBwaJSVYIxUFsDv3M8ofmx9yWTog9BfvIu0q41lo=
diff --git a/app/main.go b/app/main.go
index 550b219ae..e675350b4 100644
--- a/app/main.go
+++ b/app/main.go
@@ -5,6 +5,7 @@ import (
 	"fmt"
 	"os"
 
+	"github.com/pkg/errors"
 	"github.com/wailsapp/wails/v2"
 	"github.com/wailsapp/wails/v2/pkg/logger"
 	"github.com/wailsapp/wails/v2/pkg/options"
@@ -24,13 +25,16 @@ func main() {
 }
 
 func run() error {
-	app := newApp()
+	app, err := newApp()
+	if err != nil {
+		return errors.Wrap(err, "newApp")
+	}
 	wailsLogLevel := logger.ERROR
 	app.Verbose = true
 	if app.Verbose {
 		wailsLogLevel = logger.DEBUG
 	}
-	err := wails.Run(&options.App{
+	err = wails.Run(&options.App{
 		Title:             "xbar",
 		Width:             1080,
 		Height:            700,
diff --git a/app/package.sh b/app/package.sh
index 00ebcaa07..f9fc5ef11 100755
--- a/app/package.sh
+++ b/app/package.sh
@@ -17,6 +17,8 @@ echo -n $VERSION > .version
 # run all tests
 ./test.sh
 
+rm -rf ./build
+
 sed "s/0.0.0/${VERSION}/" ./assets/mac/info.plist.src > ./assets/mac/info.plist
 CGO_LDFLAGS=-mmacosx-version-min=10.13 wails build -package -production -platform darwin/amd64
 #CGO_LDFLAGS=-mmacosx-version-min=10.13 wails build -package -production -platform darwin/arm64
diff --git a/app/plugins_service.go b/app/plugins_service.go
index 0277f3b33..1371a5245 100644
--- a/app/plugins_service.go
+++ b/app/plugins_service.go
@@ -29,6 +29,7 @@ type PluginsService struct {
 	// osLock is used whenever there are operating system changes,
 	// like renaming files. This prevents overlap and potentially strange
 	// state.
+	// todo: move this to a better place.
 	osLock sync.Mutex
 
 	// OnRefresh is called whenever the menus should
diff --git a/app/settings.go b/app/settings.go
new file mode 100644
index 000000000..52001e8de
--- /dev/null
+++ b/app/settings.go
@@ -0,0 +1,53 @@
+package main
+
+import (
+	"encoding/json"
+	"io/ioutil"
+	"os"
+	"path/filepath"
+
+	"github.com/pkg/errors"
+)
+
+type settings struct {
+	path string `json:"-"`
+
+	// AutoUpdate indicates that xbar should automatically
+	// update itself.
+	AutoUpdate bool `json:"autoupdate"`
+}
+
+func loadSettings(path string) (*settings, error) {
+	s := &settings{
+		path: path,
+	}
+	b, err := ioutil.ReadFile(path)
+	if err != nil {
+		if os.IsNotExist(err) {
+			// file not found - it's ok, just use defaults
+			return s, nil
+		}
+		return nil, errors.Wrap(err, "ReadFile")
+	}
+	err = json.Unmarshal(b, s)
+	if err != nil {
+		return nil, errors.Wrap(err, "Unmarshal")
+	}
+	return s, nil
+}
+
+func (s *settings) save() error {
+	b, err := json.MarshalIndent(s, "", "\t")
+	if err != nil {
+		return errors.Wrap(err, "MarshalIndent")
+	}
+	err = os.MkdirAll(filepath.Dir(s.path), 0777)
+	if err != nil {
+		return errors.Wrap(err, "MkdirAll")
+	}
+	err = ioutil.WriteFile(s.path, b, 0777)
+	if err != nil {
+		return errors.Wrap(err, "WriteFile")
+	}
+	return nil
+}
diff --git a/app/settings_test.go b/app/settings_test.go
new file mode 100644
index 000000000..1d5a2160d
--- /dev/null
+++ b/app/settings_test.go
@@ -0,0 +1,29 @@
+package main
+
+import (
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/matryer/is"
+)
+
+func TestSettings(t *testing.T) {
+	is := is.New(t)
+
+	t.Cleanup(func() {
+		os.RemoveAll(filepath.Join("testdata", "settings.json"))
+	})
+
+	s, err := loadSettings(filepath.Join("testdata", "settings.json"))
+	is.NoErr(err)
+	s.AutoUpdate = true
+
+	err = s.save()
+	is.NoErr(err)
+
+	s, err = loadSettings(filepath.Join("testdata", "settings.json"))
+	is.NoErr(err)
+	is.Equal(s.AutoUpdate, true)
+
+}
diff --git a/pkg/update/update_test.go b/pkg/update/update_test.go
index 247229e3b..eece1697b 100644
--- a/pkg/update/update_test.go
+++ b/pkg/update/update_test.go
@@ -77,7 +77,8 @@ func TestUpdate(t *testing.T) {
 	apiServer := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		version := "v2.0.0"
 		response := Release{
-			TagName: version,
+			CreatedAtString: time.Now().Format(time.RFC3339Nano),
+			TagName:         version,
 			Assets: []Asset{
 				{
 					Name:               "xbar-" + version + ".tar.gz",
@@ -129,7 +130,8 @@ func TestMatchingVersions(t *testing.T) {
 	apiServer := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		version := "v2.1.0"
 		response := Release{
-			TagName: version,
+			CreatedAtString: time.Now().Format(time.RFC3339Nano),
+			TagName:         version,
 			Assets: []Asset{
 				{
 					Name:               "xbar-" + version + ".tar.gz",
@@ -176,7 +178,8 @@ func TestLocalVersionIsHigher(t *testing.T) {
 	apiServer := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		version := "v2.1.0"
 		response := Release{
-			TagName: version,
+			CreatedAtString: time.Now().Format(time.RFC3339Nano),
+			TagName:         version,
 			Assets: []Asset{
 				{
 					Name:               "xbar-" + version + ".tar.gz",