diff --git a/main.go b/main.go
index da5c5db36..510e2baf1 100644
--- a/main.go
+++ b/main.go
@@ -10,7 +10,7 @@ import (
 	"github.com/Notifiarr/notifiarr/pkg/ui"
 )
 
-// @title Notifiarr Client API Docs
+// @title Notifiarr Client API Documentation
 // @version 1.0
 // @description Notifiarr Client monitors local services and sends notifications.
 // @termsOfService https://notifiarr.com
@@ -27,14 +27,16 @@ func main() {
 	log.SetFlags(log.LstdFlags)
 	log.SetPrefix("[ERROR] ")
 
-	defer func() {
-		if r := recover(); r != nil {
-			log.Printf("Go Panic! %s\n%v\n%s", mnd.BugIssue, r, string(debug.Stack()))
-		}
-	}()
+	defer logPanic()
 
 	if err := client.Start(); err != nil {
-		_, _ = ui.Error(mnd.Title, err.Error())
-		log.Fatal(err) //nolint:gocritic // defer does not need to run if we have an error.
+		_, _ = ui.Error(err.Error())
+		defer log.Fatal(err)
+	}
+}
+
+func logPanic() {
+	if r := recover(); r != nil {
+		log.Printf("Go Panic! %s\n%v\n%s", mnd.BugIssue, r, string(debug.Stack()))
 	}
 }
diff --git a/pkg/bindata/templates/includes/footer.html b/pkg/bindata/templates/includes/footer.html
index 7cbd15c3f..b107cab29 100644
--- a/pkg/bindata/templates/includes/footer.html
+++ b/pkg/bindata/templates/includes/footer.html
@@ -2,7 +2,7 @@
                     </div> <!-- index :: content-wrapper -->
                 </div> <!-- index :: ts-main-content -->
             </div> <!-- index :: page-body -->
-            <div class="page-footer {{if not .Flags.ConfigFile}}bk-danger{{end}}">
+            <div class="page-footer{{if not .Flags.ConfigFile}} bk-danger{{end}}">
                 {{- if not .Flags.ConfigFile}}
                 <div style="display:none;" class="dialogText">
                     The application is currently running without a config file. Saving changes is disabled.
diff --git a/pkg/client/client_darwin.go b/pkg/client/client_darwin.go
index 0482cc0d0..7825c7806 100644
--- a/pkg/client/client_darwin.go
+++ b/pkg/client/client_darwin.go
@@ -2,7 +2,6 @@ package client
 
 import (
 	"context"
-	"fmt"
 	"os"
 	"os/signal"
 	"syscall"
@@ -10,22 +9,10 @@ import (
 	"github.com/Notifiarr/notifiarr/pkg/website"
 )
 
-/*
-func (c *Client) handleAptHook() error {
-	return fmt.Errorf("this feature is not supported on this platform") //nolint:goerr113
-}
-*/
-
 func (c *Client) handleAptHook(_ context.Context) error {
-	return fmt.Errorf("this feature is not supported on this platform") //nolint:goerr113
+	return ErrUnsupport
 }
 
-func (c *Client) printUpdateMessage() {}
-
-func (c *Client) upgradeWindows(_, _ interface{}) {}
-
-func (c *Client) AutoWatchUpdate(_ interface{}) {}
-
 func (c *Client) checkReloadSignal(ctx context.Context, sigc os.Signal) error {
 	return c.reloadConfiguration(ctx, website.EventSignal, "Caught Signal: "+sigc.String())
 }
diff --git a/pkg/client/client_linux.go b/pkg/client/client_linux.go
index 4b5b9a0ea..f935d70f0 100644
--- a/pkg/client/client_linux.go
+++ b/pkg/client/client_linux.go
@@ -67,12 +67,6 @@ func (c *Client) handleAptHook(ctx context.Context) error {
 	return nil
 }
 
-func (c *Client) printUpdateMessage()             {}
-func (c *Client) upgradeWindows(_, _ interface{}) {}
-
-// AutoWatchUpdate is not used on this OS.
-func (c *Client) AutoWatchUpdate(_ interface{}) {}
-
 func (c *Client) checkReloadSignal(ctx context.Context, sigc os.Signal) error {
 	return c.reloadConfiguration(ctx, website.EventSignal, "Caught Signal: "+sigc.String())
 }
diff --git a/pkg/client/client_other.go b/pkg/client/client_other.go
index 0d1614f4f..8d413d810 100644
--- a/pkg/client/client_other.go
+++ b/pkg/client/client_other.go
@@ -4,7 +4,6 @@ package client
 
 import (
 	"context"
-	"fmt"
 	"os"
 	"os/signal"
 	"syscall"
@@ -13,26 +12,22 @@ import (
 )
 
 // If you need more fake methods, add them.
-//
+
 //nolint:gochecknoglobals
 var menu = make(map[string]*fakeMenu)
 
 type fakeMenu struct{}
 
-func (f *fakeMenu) Uncheck()               {}
-func (f *fakeMenu) Check()                 {}
-func (f *fakeMenu) SetTooltip(interface{}) {}
+func (f *fakeMenu) Uncheck()       {}
+func (f *fakeMenu) Check()         {}
+func (f *fakeMenu) SetTooltip(any) {}
 
-func (c *Client) printUpdateMessage()        {}
-func (c *Client) setupMenus(interface{})     {}
-func (c *Client) startTray(_, _ interface{}) {}
+func (c *Client) setupMenus(any)     {}
+func (c *Client) startTray(_, _ any) {}
 func (c *Client) handleAptHook(_ context.Context) error {
-	return fmt.Errorf("this feature is not supported on this platform") //nolint:goerr113
+	return ErrUnsupport
 }
 
-// AutoWatchUpdate is not used on this OS.
-func (c *Client) AutoWatchUpdate(_ interface{}) {}
-
 func (c *Client) checkReloadSignal(ctx context.Context, sigc os.Signal) error {
 	return c.reloadConfiguration(ctx, website.EventSignal, "Caught Signal: "+sigc.String())
 }
diff --git a/pkg/client/client_windows.go b/pkg/client/client_windows.go
index 3f3c53efe..2eb6a7871 100644
--- a/pkg/client/client_windows.go
+++ b/pkg/client/client_windows.go
@@ -2,157 +2,15 @@ package client
 
 import (
 	"context"
-	"fmt"
 	"os"
 	"os/signal"
 	"syscall"
-	"time"
 
-	"github.com/Notifiarr/notifiarr/pkg/mnd"
-	"github.com/Notifiarr/notifiarr/pkg/ui"
-	"github.com/Notifiarr/notifiarr/pkg/update"
 	"github.com/Notifiarr/notifiarr/pkg/website"
-	"github.com/hako/durafmt"
-	"github.com/kardianos/osext"
-	"golift.io/version"
 )
 
-// WaitTime is how long we wait, after startup, before doing an update check.
-const WaitTime = 10 * time.Minute
-
-// This is the pop-up a user sees when they click update in the menu.
-func (c *Client) upgradeWindows(ctx context.Context, update *update.Update) {
-	yes, _ := ui.Question(mnd.Title, "An Update is available! Upgrade Now?\n\n"+
-		"Your Version: "+version.Version+"-"+version.Revision+"\n"+
-		"New Version: "+update.Current+"\n"+
-		"Date: "+update.RelDate.Format("Jan 2, 2006")+mnd.DurationAge(update.RelDate), false)
-	if yes {
-		if err := c.updateNow(ctx, update, "user requested"); err != nil {
-			c.Errorf("Update Failed: %v", err)
-			_, _ = ui.Error(mnd.Title+" ERROR", "Updating Notifiarr:\n"+err.Error()+"\n")
-		}
-	}
-}
-
-func (c *Client) printUpdateMessage() {
-	if !c.Flags.Updated {
-		return
-	}
-
-	err := ui.Notify(mnd.Title + " updated to version " + version.Version)
-	if err != nil {
-		c.Error("Creating Toast Notification:", err)
-	}
-}
-
-func (c *Client) AutoWatchUpdate(ctx context.Context) {
-	defer c.CapturePanic()
-
-	var dur time.Duration
-
-	switch c.Config.AutoUpdate {
-	case "off", "no", "disabled", "disable", "false", "", "-", "0", "0s":
-		return
-	case "hourly":
-		dur = time.Hour
-	case "daily":
-		dur = mnd.OneDay
-	default:
-		var err error
-		if dur, err = time.ParseDuration(c.Config.AutoUpdate); err != nil {
-			dur = mnd.OneDay
-			break
-		}
-
-		if dur < time.Hour {
-			dur = time.Hour
-		}
-	}
-
-	c.startAutoUpdater(ctx, dur)
-}
-
-func (c *Client) startAutoUpdater(ctx context.Context, dur time.Duration) {
-	pfx := ""
-	if c.Config.UnstableCh {
-		pfx = "Unstable Channel "
-	}
-
-	time.Sleep(WaitTime)
-	c.Print(pfx+"Auto-updater started. Check interval:", durafmt.Parse(dur).LimitFirstN(3)) //nolint:mnd
-
-	// Check for update on startup.
-	if err := c.checkAndUpdate(ctx, "startup check"); err != nil {
-		c.Errorf("Startup-Update Failed: %v", err)
-	}
-
-	ticker := time.NewTicker(dur)
-	for range ticker.C { // This is a never-ending loop.
-		if err := c.checkAndUpdate(ctx, "automatic"); err != nil {
-			c.Errorf("Auto-Update Failed: %v", err)
-		}
-	}
-}
-
-func (c *Client) checkAndUpdate(ctx context.Context, how string) error {
-	var (
-		data *update.Update
-		err  error
-	)
-
-	//nolint:wsl
-	if c.Config.UnstableCh {
-		c.Debugf("[cron requested] Checking Unstable website for Update.")
-		data, err = update.CheckUnstable(ctx, mnd.DefaultName, version.Revision)
-	} else {
-		c.Debugf("[cron requested] Checking GitHub for Update.")
-		data, err = update.CheckGitHub(ctx, mnd.UserRepo, version.Version)
-	}
-
-	if err != nil {
-		return fmt.Errorf("checking for update: %w", err)
-	} else if !data.Outdate {
-		return nil
-	} else if err = c.updateNow(ctx, data, how); err != nil {
-		return err
-	}
-
-	return nil
-}
-
-func (c *Client) updateNow(ctx context.Context, u *update.Update, msg string) error {
-	c.Printf("[UPDATE] Downloading and installing update! %s-%s => %s: %s",
-		version.Version, version.Revision, u.Current, u.CurrURL)
-
-	cmd := &update.Command{
-		URL:    u.CurrURL,
-		Logger: c.Logger.DebugLog,
-		Args:   []string{"--restart", "--config", c.Flags.ConfigFile},
-		Path:   os.Args[0],
-	}
-
-	if path, err := osext.Executable(); err == nil {
-		cmd.Path = path
-	}
-
-	// This downloads the new file to a temp name in the same folder as the running file.
-	// Moves the running file to a backup name in the same folder.
-	// Moves the new file to the same location that the running file was at.
-	// Triggers another invocation of the app that sleeps 5 seconds then restarts.
-	backupFile, err := update.Now(ctx, cmd)
-	if err != nil {
-		return fmt.Errorf("installing update: %w", err)
-	}
-
-	c.Printf("Update installed to %s restarting! Backup: %s", cmd.Path, backupFile)
-	// And exit, so we can restart.
-	c.sigkil <- &update.Signal{Text: "upgrade request: " + msg}
-
-	return nil
-}
-
-func (c *Client) handleAptHook(_ interface{}) error {
-	return fmt.Errorf("this feature is not supported on this platform") //nolint:goerr113
+func (c *Client) handleAptHook(_ any) error {
+	return ErrUnsupport
 }
 
 func (c *Client) checkReloadSignal(ctx context.Context, sigc os.Signal) error {
diff --git a/pkg/client/start.go b/pkg/client/start.go
index 4e7488b4f..c1b0dabea 100644
--- a/pkg/client/start.go
+++ b/pkg/client/start.go
@@ -64,7 +64,8 @@ type customReload struct {
 
 // Errors returned by this package.
 var (
-	ErrNilAPIKey = fmt.Errorf("API key may not be empty: set a key in config file, OR with environment variable")
+	ErrUnsupport = errors.New("this feature is not supported on this platform")
+	ErrNilAPIKey = errors.New("API key may not be empty: set a key in config file, OR with environment variable")
 )
 
 // newDefaults returns a new Client pointer with default settings.
@@ -160,7 +161,10 @@ func (c *Client) start(ctx context.Context, msg, newPassword string) error {
 		os.Getpid(), os.Getuid(), os.Getgid(),
 		version.Started.Format("Mon, Jan 2, 2006 @ 3:04:05 PM MST -0700"))
 	c.Printf("==> %s", msg)
-	c.printUpdateMessage()
+
+	if c.Flags.Updated {
+		go ui.Notify(mnd.Title + " updated to version " + version.Version) //nolint:errcheck
+	}
 
 	if err := c.loadAssetsTemplates(ctx); err != nil {
 		return err
@@ -171,9 +175,6 @@ func (c *Client) start(ctx context.Context, msg, newPassword string) error {
 	if newPassword != "" {
 		// If newPassword is set it means we need to write out a new config file for a new installation. Do that now.
 		c.makeNewConfigFile(ctx, newPassword)
-	} else if c.Config.AutoUpdate != "" {
-		// do not run updater if there's a brand new config file.
-		go c.AutoWatchUpdate(ctx)
 	}
 
 	if ui.HasGUI() {
@@ -191,11 +192,11 @@ func (c *Client) makeNewConfigFile(ctx context.Context, newPassword string) {
 
 	_, _ = c.Config.Write(ctx, c.Flags.ConfigFile, false)
 	_ = ui.OpenFile(c.Flags.ConfigFile)
-	_, _ = ui.Warning(mnd.Title, "A new configuration file was created @ "+
-		c.Flags.ConfigFile+" - it should open in a text editor. "+
-		"Please edit the file and reload this application using the tray menu. "+
-		"Your Web UI password was set to "+newPassword+
-		" and was also printed in the log file '"+c.Config.LogFile+"' and/or app ouptput.")
+	_, _ = ui.Warning("A new configuration file was created @ " +
+		c.Flags.ConfigFile + " - it should open in a text editor. " +
+		"Please edit the file and reload this application using the tray menu. " +
+		"Your Web UI password was set to " + newPassword +
+		" and was also printed in the log file '" + c.Config.LogFile + "' and/or app output.")
 }
 
 // loadConfiguration brings in, and sometimes creates, the initial running configuration.
@@ -259,7 +260,7 @@ func (c *Client) configureServices(ctx context.Context) *clientinfo.ClientInfo {
 	c.configureServicesPlex(ctx)
 	c.Config.Snapshot.Validate()
 	c.PrintStartupInfo(ctx, clientInfo)
-	c.triggers.Start(ctx, c.sighup)
+	c.triggers.Start(ctx, c.sighup, c.sigkil)
 	c.Config.Services.Start(ctx)
 
 	return clientInfo
diff --git a/pkg/client/tray.go b/pkg/client/tray.go
index 6dbb7892b..9eb6e0493 100644
--- a/pkg/client/tray.go
+++ b/pkg/client/tray.go
@@ -125,11 +125,11 @@ func (c *Client) makeMenus(ctx context.Context, clientInfo *clientinfo.ClientInf
 	c.debugMenu()
 
 	menu["update"] = systray.AddMenuItem("Update", "check GitHub for updated version")
-	menu["update"].Click(func() { go c.checkForUpdate(ctx, false) })
+	menu["update"].Click(func() { go c.triggers.AutoUpdate.CheckForUpdate(ctx, false) })
 
 	if mnd.IsUnstable || (clientInfo != nil && clientInfo.User.DevAllowed) {
 		menu["unstable"] = systray.AddMenuItem("Unstable", "check Unstable website for updated version")
-		menu["unstable"].Click(func() { go c.checkForUpdate(ctx, true) })
+		menu["unstable"].Click(func() { go c.triggers.AutoUpdate.CheckForUpdate(ctx, true) })
 	}
 
 	menu["gui"] = systray.AddMenuItem("Open WebUI", "open the web page for this Notifiarr client")
@@ -149,7 +149,7 @@ func (c *Client) configMenu(ctx context.Context) {
 
 	menu["view"] = conf.AddSubMenuItem("View", "show configuration")
 	menu["view"].Click(func() {
-		go ui.Info(mnd.Title+": Configuration", c.displayConfig())
+		go ui.Info(c.displayConfig())
 	})
 
 	menu["edit"] = conf.AddSubMenuItem("Edit", "edit configuration")
diff --git a/pkg/client/tray_commands.go b/pkg/client/tray_commands.go
index 274155a1e..9d173a243 100644
--- a/pkg/client/tray_commands.go
+++ b/pkg/client/tray_commands.go
@@ -5,20 +5,14 @@ package client
 import (
 	"context"
 	"fmt"
-	"runtime"
 	"strings"
 
 	"github.com/Notifiarr/notifiarr/pkg/configfile"
-	"github.com/Notifiarr/notifiarr/pkg/mnd"
 	"github.com/Notifiarr/notifiarr/pkg/ui"
-	"github.com/Notifiarr/notifiarr/pkg/update"
-	"golift.io/version"
 )
 
 /* This file contains methods that are triggered from the GUI menu. */
 
-const TitleError = mnd.Title + " Error"
-
 func (c *Client) toggleServer(ctx context.Context) {
 	if !menu["stat"].Checked() {
 		ui.Notify("Started web server") //nolint:errcheck
@@ -49,54 +43,6 @@ func (c *Client) rotateLogs() {
 	}
 }
 
-func (c *Client) checkForUpdate(ctx context.Context, unstable bool) {
-	var (
-		data  *update.Update
-		err   error
-		where = "GitHub"
-	)
-
-	if unstable {
-		c.Print("[user requested] Unstable Update Check")
-
-		data, err = update.CheckUnstable(ctx, mnd.Title, version.Revision)
-		where = "Unstable website"
-	} else {
-		c.Print("[user requested] GitHub Update Check")
-
-		data, err = update.CheckGitHub(ctx, mnd.UserRepo, version.Version)
-	}
-
-	switch {
-	case err != nil:
-		c.Errorf("Update Check: %v", err)
-		_, _ = ui.Error(TitleError, "Checking version on "+where+": "+err.Error())
-	case data.Outdate && runtime.GOOS == mnd.Windows:
-		c.upgradeWindows(ctx, data)
-	case data.Outdate:
-		c.downloadOther(data, unstable)
-	default:
-		_, _ = ui.Info(mnd.Title, "You're up to date! Version: "+data.Current+"\n"+
-			"Updated: "+data.RelDate.Format("Jan 2, 2006")+mnd.DurationAge(data.RelDate))
-	}
-}
-
-func (c *Client) downloadOther(update *update.Update, unstable bool) {
-	msg := "An Update is available! Download?\n\n"
-
-	if unstable {
-		msg = "An Unstable Update is available! Download?\n\n"
-	}
-
-	yes, _ := ui.Question(mnd.Title, msg+
-		"Your Version: "+version.Version+"-"+version.Revision+"\n"+
-		"New Version: "+update.Current+"\n"+
-		"Date: "+update.RelDate.Format("Jan 2, 2006")+mnd.DurationAge(update.RelDate), false)
-	if yes {
-		_ = ui.OpenURL(update.CurrURL)
-	}
-}
-
 // This is always outdated. :( The format on screen sucks anyway. This should probably be removed.
 func (c *Client) displayConfig() (s string) { //nolint: funlen,cyclop
 	s = "Config File: " + c.Flags.ConfigFile
@@ -163,10 +109,10 @@ func (c *Client) displayConfig() (s string) { //nolint: funlen,cyclop
 }
 
 func (c *Client) writeConfigFile(ctx context.Context) {
-	val, _, _ := ui.Entry(mnd.Title, "Enter path to write config file:", c.Flags.ConfigFile)
+	val, _, _ := ui.Entry("Enter path to write config file:", c.Flags.ConfigFile)
 
 	if val == "" {
-		_, _ = ui.Error(TitleError, "No Config File Provided")
+		_, _ = ui.Error("No Config File Provided")
 		return
 	}
 
@@ -174,18 +120,18 @@ func (c *Client) writeConfigFile(ctx context.Context) {
 
 	if _, err := c.Config.Write(ctx, val, false); err != nil {
 		c.Errorf("Writing Config File: %v", err)
-		_, _ = ui.Error(TitleError, "Writing Config File: "+err.Error())
+		_, _ = ui.Error("Writing Config File: " + err.Error())
 
 		return
 	}
 
-	_, _ = ui.Info(mnd.Title, "Wrote Config File: "+val)
+	_, _ = ui.Info("Wrote Config File: " + val)
 }
 
 func (c *Client) menuPanic() {
 	defer c.CapturePanic()
 
-	yes, err := ui.Question(mnd.Title, "You really want to panic?", true)
+	yes, err := ui.Question("You really want to panic?", true)
 	if !yes || err != nil {
 		return
 	}
@@ -206,7 +152,7 @@ func (c *Client) openGUI() {
 }
 
 func (c *Client) updatePassword(ctx context.Context) {
-	pass, _, err := ui.Entry(mnd.Title, "Enter new Web UI admin password (must be 9+ characters):", "")
+	pass, _, err := ui.Entry("Enter new Web UI admin password (must be 9+ characters):", "")
 	if err != nil {
 		c.Errorf("err: %v", err)
 		return
@@ -228,7 +174,7 @@ func (c *Client) updatePassword(ctx context.Context) {
 
 	if err := c.Config.UIPassword.Set(configfile.DefaultUsername + ":" + pass); err != nil {
 		c.Errorf("Updating Web UI Password: %v", err)
-		_, _ = ui.Error(TitleError, "Updating Web UI Password: "+err.Error())
+		_, _ = ui.Error("Updating Web UI Password: " + err.Error())
 	}
 
 	if err = ui.Notify("Web UI password updated. Save config to persist this change."); err != nil {
diff --git a/pkg/configfile/config.go b/pkg/configfile/config.go
index d00544931..e404d35b7 100644
--- a/pkg/configfile/config.go
+++ b/pkg/configfile/config.go
@@ -174,7 +174,7 @@ func (c *Config) Get(flag *Flags, logger *logs.Logger) (*website.Server, *trigge
 		BindAddr: c.BindAddr,
 	})
 
-	return c.Services.Website, c.setup(logger), err
+	return c.Services.Website, c.setup(logger, flag), err
 }
 
 func (c *Config) fixConfig() {
@@ -192,7 +192,7 @@ func (c *Config) fixConfig() {
 	c.Services.Plugins = c.Snapshot.Plugins
 }
 
-func (c *Config) setup(logger *logs.Logger) *triggers.Actions {
+func (c *Config) setup(logger *logs.Logger, flag *Flags) *triggers.Actions {
 	c.URLBase = strings.TrimSuffix(path.Join("/", c.URLBase), "/") + "/"
 	c.Allow = MakeIPs(c.Upstreams)
 
@@ -219,6 +219,9 @@ func (c *Config) setup(logger *logs.Logger) *triggers.Actions {
 		LogFiles:   c.LogConfig.GetActiveLogFilePaths(),
 		Commands:   c.Commands,
 		CIC:        cic,
+		ConfigFile: flag.ConfigFile,
+		AutoUpdate: c.AutoUpdate,
+		UnstableCh: c.UnstableCh,
 		Services:   c.Services,
 		Logger:     logger,
 	})
diff --git a/pkg/triggers/autoupdate/autoupdate.go b/pkg/triggers/autoupdate/autoupdate.go
new file mode 100644
index 000000000..33f8d2405
--- /dev/null
+++ b/pkg/triggers/autoupdate/autoupdate.go
@@ -0,0 +1,188 @@
+package autoupdate
+
+import (
+	"context"
+	"fmt"
+	"os"
+	"sync"
+	"time"
+
+	"github.com/Notifiarr/notifiarr/pkg/mnd"
+	"github.com/Notifiarr/notifiarr/pkg/triggers/common"
+	"github.com/Notifiarr/notifiarr/pkg/update"
+	"github.com/Notifiarr/notifiarr/pkg/website"
+	"github.com/hako/durafmt"
+	"github.com/kardianos/osext"
+	"golift.io/cnfg"
+	"golift.io/version"
+)
+
+// TrigAutoUpdate is our auto update trigger identifier.
+const TrigAutoUpdate common.TriggerName = "Automatically check for application update."
+
+const (
+	minimumUpdateDur = 1 * time.Hour
+	// waitTime is how long we wait, after startup, before doing an update check.
+	waitTime = 6 * time.Minute
+)
+
+// Action contains the exported methods for this package.
+type Action struct {
+	cmd *cmd
+}
+
+type cmd struct {
+	*common.Config
+	AutoUpdate string
+	UnstableCh bool
+	ConfigFile string
+	sync.Mutex
+	stop bool
+}
+
+// New configures the library.
+func New(config *common.Config, autoUpdate, configFile string, unstable bool) *Action {
+	return &Action{cmd: &cmd{
+		Config:     config,
+		AutoUpdate: autoUpdate,
+		UnstableCh: unstable,
+		ConfigFile: configFile,
+	}}
+}
+
+// Run checks for an update a few minutes after the app starts up.
+func (a *Action) Run(ctx context.Context) {
+	if !mnd.IsWindows {
+		return // Auto update only works on Windows.
+	}
+
+	time.Sleep(waitTime)
+	a.cmd.Lock()
+	defer a.cmd.Unlock()
+
+	if !a.cmd.stop { // Check for update on startup, after a short wait.
+		a.cmd.checkAndUpdate(ctx, &common.ActionInput{Type: website.EventStart})
+	}
+}
+
+// Create initializes the library.
+func (a *Action) Create() {
+	if !mnd.IsWindows {
+		return // Auto update only works on Windows.
+	}
+
+	a.cmd.create()
+}
+
+// Stop satisfies an interface.
+func (a *Action) Stop() {
+	a.cmd.Lock()
+	defer a.cmd.Unlock()
+	a.cmd.stop = true
+}
+
+// Verify the interfaces are satisfied.
+var (
+	_ = common.Run(&Action{nil})
+	_ = common.Create(&Action{nil})
+)
+
+// Run fires in a go routine. Wait a minute or two then tell the website we're up.
+// If app reloads in first checkWait duration, this throws an error. That's ok.
+func (c *cmd) create() {
+	defer c.CapturePanic()
+
+	var dur time.Duration
+
+	switch c.AutoUpdate {
+	case "off", "no", "disabled", "disable", "false", "", "-", "0", "0s":
+		return
+	case "hourly":
+		dur = time.Hour
+	case "daily":
+		dur = mnd.OneDay
+	default:
+		var err error
+		if dur, err = time.ParseDuration(c.AutoUpdate); err != nil {
+			dur = mnd.OneDay
+			break
+		}
+
+		if dur < minimumUpdateDur {
+			dur = minimumUpdateDur
+		}
+	}
+
+	pfx := "GitHub"
+	if c.UnstableCh {
+		pfx = "Unstable"
+	}
+
+	c.Printf("==> Client auto-updater started. %s channel check interval: %s",
+		pfx, durafmt.Parse(dur).LimitFirstN(3)) //nolint:mnd
+
+	c.Add(&common.Action{
+		Name: TrigAutoUpdate,
+		Fn:   c.checkAndUpdate,
+		D:    cnfg.Duration{Duration: dur},
+	})
+}
+
+func (c *cmd) checkAndUpdate(ctx context.Context, action *common.ActionInput) {
+	var (
+		data *update.Update
+		err  error
+	)
+
+	if !mnd.IsWindows {
+		return // Only Windows can auto update.
+	}
+
+	//nolint:wsl
+	if c.UnstableCh {
+		c.Debugf("[cron requested] Checking Unstable website for Update.")
+		data, err = update.CheckUnstable(ctx, mnd.DefaultName, version.Revision)
+	} else {
+		c.Debugf("[cron requested] Checking GitHub for Update.")
+		data, err = update.CheckGitHub(ctx, mnd.UserRepo, version.Version)
+	}
+
+	if err != nil {
+		c.Errorf("Auto-Update Failed checking for update: %v", err)
+	} else if !data.Outdate {
+		c.Debugf("Auto-Update Success, up to date.")
+	} else if err = c.updateNow(ctx, data, action.Type); err != nil {
+		c.Errorf("Auto-Update Failed applying update: %v", err)
+	}
+}
+
+func (c *cmd) updateNow(ctx context.Context, u *update.Update, msg website.EventType) error {
+	c.Printf("[UPDATE] Downloading and installing update! %s-%s => %s: %s",
+		version.Version, version.Revision, u.Current, u.CurrURL)
+
+	cmd := &update.Command{
+		URL:    u.CurrURL,
+		Logger: c.Logger.DebugLog,
+		Args:   []string{"--restart", "--config", c.ConfigFile},
+		Path:   os.Args[0],
+	}
+
+	if path, err := osext.Executable(); err == nil {
+		cmd.Path = path
+	}
+
+	// This downloads the new file to a temp name in the same folder as the running file.
+	// Moves the running file to a backup name in the same folder.
+	// Moves the new file to the same location that the running file was at.
+	// Triggers another invocation of the app that sleeps 5 seconds then restarts.
+	backupFile, err := update.Now(ctx, cmd)
+	if err != nil {
+		return fmt.Errorf("installing update: %w", err)
+	}
+
+	c.Printf("Update installed to %s restarting! Backup: %s", cmd.Path, backupFile)
+	// And exit, so we can restart.
+	c.StopApp("upgrade request: " + string(msg))
+
+	return nil
+}
diff --git a/pkg/triggers/autoupdate/update.go b/pkg/triggers/autoupdate/update.go
new file mode 100644
index 000000000..4c73fece2
--- /dev/null
+++ b/pkg/triggers/autoupdate/update.go
@@ -0,0 +1,81 @@
+package autoupdate
+
+/* This file handles manual update requests. */
+
+import (
+	"context"
+	"runtime"
+
+	"github.com/Notifiarr/notifiarr/pkg/mnd"
+	"github.com/Notifiarr/notifiarr/pkg/ui"
+	"github.com/Notifiarr/notifiarr/pkg/update"
+	"golift.io/version"
+)
+
+// CheckForUpdate is called by a user clicking in the menu/tray icon.
+func (a *Action) CheckForUpdate(ctx context.Context, unstable bool) {
+	a.cmd.checkForUpdates(ctx, unstable)
+}
+
+func (c *cmd) checkForUpdates(ctx context.Context, unstable bool) {
+	var (
+		data  *update.Update
+		err   error
+		where = "GitHub"
+	)
+
+	if unstable {
+		c.Print("[user requested] Unstable Update Check")
+
+		data, err = update.CheckUnstable(ctx, mnd.Title, version.Revision)
+		where = "Unstable website"
+	} else {
+		c.Print("[user requested] GitHub Update Check")
+
+		data, err = update.CheckGitHub(ctx, mnd.UserRepo, version.Version)
+	}
+
+	switch {
+	case err != nil:
+		c.Errorf("%s Update Check: %v", where, err)
+		_, _ = ui.Error("Checking version on " + where + ": " + err.Error())
+	case data.Outdate && runtime.GOOS == mnd.Windows:
+		c.upgradeWindows(ctx, data)
+	case data.Outdate:
+		c.downloadUpdate(data, unstable)
+	default:
+		_, _ = ui.Info("You're up to date! Version: " + data.Current + " @ " + where + "\n" +
+			"Updated: " + data.RelDate.Format("Jan 2, 2006") + mnd.DurationAge(data.RelDate))
+	}
+}
+
+// upgradeWindows is the pop-up a Windows user sees when they click update in the menu.
+func (c *cmd) upgradeWindows(ctx context.Context, update *update.Update) {
+	yes, _ := ui.Question("An Update is available! Upgrade Now?\n\n"+
+		"Your Version: "+version.Version+"-"+version.Revision+"\n"+
+		"New Version: "+update.Current+"\n"+
+		"Date: "+update.RelDate.Format("Jan 2, 2006")+mnd.DurationAge(update.RelDate), false)
+	if yes {
+		if err := c.updateNow(ctx, update, "user requested"); err != nil {
+			c.Errorf("Application Update Failed: %v", err)
+			_, _ = ui.Error("Updating Notifiarr:\n" + err.Error() + "\n")
+		}
+	}
+}
+
+// downloadUpdate is the pop-up a mac user sees when they click update in the menu.
+func (c *cmd) downloadUpdate(update *update.Update, unstable bool) {
+	msg := "An Update from GitHub is available! Download?\n\n"
+
+	if unstable {
+		msg = "An Unstable Update is available! Download?\n\n"
+	}
+
+	yes, _ := ui.Question(msg+
+		"Your Version: "+version.Version+"-"+version.Revision+"\n"+
+		"New Version: "+update.Current+"\n"+
+		"Date: "+update.RelDate.Format("Jan 2, 2006")+mnd.DurationAge(update.RelDate), false)
+	if yes {
+		_ = ui.OpenURL(update.CurrURL)
+	}
+}
diff --git a/pkg/triggers/common/triggers.go b/pkg/triggers/common/triggers.go
index 2a3c364e0..564f4f63c 100644
--- a/pkg/triggers/common/triggers.go
+++ b/pkg/triggers/common/triggers.go
@@ -34,6 +34,7 @@ type Config struct {
 	list     []*Action      // List of action triggers
 	Services                // for running service checks.
 	reloadCh chan os.Signal // so triggers can reload the app.
+	stopCh   chan os.Signal // so triggers can stop the app.
 	rand     *rand.Rand
 }
 
@@ -66,6 +67,22 @@ func (c *Config) ReloadApp(reason string) {
 	c.reloadCh <- &update.Signal{Text: reason}
 }
 
+// SetReloadCh is used to set the stop channel for triggers.
+// This is an exported method because the channel is not always
+// available when triggers are initialized.
+func (c *Config) SetStopCh(stopCh chan os.Signal) {
+	c.stopCh = stopCh
+}
+
+// StopApp shuts down the application.
+func (c *Config) StopApp(reason string) {
+	if c.stopCh == nil {
+		panic("attempt to stop with no stop channel")
+	}
+
+	c.stopCh <- &update.Signal{Text: reason}
+}
+
 // ActionInput is used to send data to a trigger action.
 type ActionInput struct {
 	Type website.EventType
@@ -149,5 +166,5 @@ func (c *Config) Rand() *rand.Rand {
 
 // WithInstance returns a trigger name with an instance ID.
 func (name TriggerName) WithInstance(instance int) TriggerName {
-	return TriggerName(fmt.Sprintf(string(name), instance))
+	return TriggerName(fmt.Sprint(name, instance))
 }
diff --git a/pkg/triggers/crontimer/custom.go b/pkg/triggers/crontimer/custom.go
index ffd83cd3e..375434a3a 100644
--- a/pkg/triggers/crontimer/custom.go
+++ b/pkg/triggers/crontimer/custom.go
@@ -5,6 +5,7 @@ import (
 	"encoding/json"
 	"fmt"
 	"strings"
+	"sync"
 	"time"
 
 	"github.com/Notifiarr/notifiarr/pkg/triggers/common"
@@ -42,6 +43,8 @@ type Action struct {
 type cmd struct {
 	*common.Config
 	list []*Timer
+	sync.Mutex
+	stop bool
 }
 
 // Timer is used to trigger actions.
@@ -86,8 +89,12 @@ func (a *Action) Create() {
 	a.cmd.create()
 }
 
-// Stop satisifies an interface.
-func (a *Action) Stop() {}
+// Stop satisfies an interface.
+func (a *Action) Stop() {
+	a.cmd.Lock()
+	defer a.cmd.Unlock()
+	a.cmd.stop = true
+}
 
 // Verify the interfaces are satisfied.
 var (
@@ -96,9 +103,17 @@ var (
 )
 
 // Run fires in a go routine. Wait a minute or two then tell the website we're up.
+// If app reloads in first checkWait duration, this throws an error. That's ok.
 func (a *Action) Run(ctx context.Context) {
-	time.Sleep(checkWait)
-	a.cmd.PollUpCheck(ctx, &common.ActionInput{Type: website.EventStart})
+	if a.cmd.ValidAPIKey() == nil {
+		time.Sleep(checkWait)
+		a.cmd.Lock()
+		defer a.cmd.Unlock()
+
+		if !a.cmd.stop { // Wait a while then make sure we didn't stop.
+			a.cmd.PollUpCheck(ctx, &common.ActionInput{Type: website.EventStart})
+		}
+	}
 }
 
 func (c *cmd) create() {
@@ -125,7 +140,7 @@ func (c *cmd) create() {
 		custom.URI = "/" + strings.TrimPrefix(custom.URI, "/")
 
 		if custom.Interval.Duration < time.Minute {
-			c.Errorf("Website provided custom cron interval under 1 minute. Interval: %s Name: %s, URI: %s",
+			c.ErrorfNoShare("Website provided custom cron interval under 1 minute. Interval: %s Name: %s, URI: %s",
 				custom.Interval, custom.Name, custom.URI)
 
 			custom.Interval.Duration = time.Minute
@@ -157,16 +172,17 @@ func (c *cmd) startWebsitePoller() {
 	})
 }
 
-func (c *cmd) PollUpCheck(ctx context.Context, input *common.ActionInput) {
+// PollUpCheck just tells the website the client is still up. It doesn't process the return payload.
+func (c *cmd) PollUpCheck(_ context.Context, input *common.ActionInput) {
 	_, err := c.GetData(&website.Request{
 		Route:      website.ClientRoute,
 		Event:      website.EventCheck,
-		Payload:    c.CIC.Info(ctx, true), // true avoids polling tautulli.
-		LogPayload: false,
+		Payload:    "up",
+		LogPayload: true,
 		ErrorsOnly: true,
 	})
 	if err != nil {
-		c.Errorf("[%s requested] Polling Notifiarr: %v", input.Type, err)
+		c.ErrorfNoShare("[%s requested] UpChecking Notifiarr: %v", input.Type, err)
 		return
 	}
 }
@@ -181,7 +197,7 @@ func (c *cmd) PollForReload(ctx context.Context, input *common.ActionInput) {
 		LogPayload: true,
 	})
 	if err != nil {
-		c.Errorf("[%s requested] Polling Notifiarr: %v", input.Type, err)
+		c.ErrorfNoShare("[%s requested] Polling Notifiarr: %v", input.Type, err)
 		return
 	}
 
@@ -192,7 +208,7 @@ func (c *cmd) PollForReload(ctx context.Context, input *common.ActionInput) {
 	}
 
 	if err = json.Unmarshal(body.Details.Response, &v); err != nil {
-		c.Errorf("[%s requested] Polling Notifiarr: %v", input.Type, err)
+		c.ErrorfNoShare("[%s requested] Polling Notifiarr: %v", input.Type, err)
 		return
 	}
 
diff --git a/pkg/triggers/triggers.go b/pkg/triggers/triggers.go
index 1474e1180..e126a3a1d 100644
--- a/pkg/triggers/triggers.go
+++ b/pkg/triggers/triggers.go
@@ -10,6 +10,7 @@ import (
 	"github.com/Notifiarr/notifiarr/pkg/apps"
 	"github.com/Notifiarr/notifiarr/pkg/logs"
 	"github.com/Notifiarr/notifiarr/pkg/snapshot"
+	"github.com/Notifiarr/notifiarr/pkg/triggers/autoupdate"
 	"github.com/Notifiarr/notifiarr/pkg/triggers/backups"
 	"github.com/Notifiarr/notifiarr/pkg/triggers/cfsync"
 	"github.com/Notifiarr/notifiarr/pkg/triggers/commands"
@@ -37,6 +38,9 @@ type Config struct {
 	LogFiles   []string
 	Commands   []*commands.Command
 	CIC        *clientinfo.Config
+	ConfigFile string
+	AutoUpdate string
+	UnstableCh bool
 	common.Services
 	*logs.Logger
 }
@@ -59,6 +63,7 @@ type Actions struct {
 	EmptyTrash *emptytrash.Action
 	MDbList    *mdblist.Action
 	FileUpload *fileupload.Action
+	AutoUpdate *autoupdate.Action
 }
 
 // New turns a populated Config into a pile of Actions.
@@ -88,6 +93,7 @@ func New(config *Config) *Actions {
 		MDbList:    mdblist.New(common),
 		FileUpload: fileupload.New(common),
 		Timers:     common,
+		AutoUpdate: autoupdate.New(common, config.AutoUpdate, config.ConfigFile, config.UnstableCh),
 	}
 }
 
@@ -95,8 +101,10 @@ func New(config *Config) *Actions {
 // They execute all Create(), Run() and Stop() procedures defined in our Actions.
 
 // Start creates all the triggers and runs the timers.
-func (a *Actions) Start(ctx context.Context, reloadCh chan os.Signal) {
+func (a *Actions) Start(ctx context.Context, reloadCh, stopCh chan os.Signal) {
 	a.Timers.SetReloadCh(reloadCh)
+	a.Timers.SetStopCh(stopCh)
+
 	defer a.Timers.Run(ctx)
 
 	actions := reflect.ValueOf(a).Elem()
diff --git a/pkg/ui/dlgs.go b/pkg/ui/dlgs.go
index 59e0a76f9..9c836753a 100644
--- a/pkg/ui/dlgs.go
+++ b/pkg/ui/dlgs.go
@@ -3,56 +3,63 @@
 package ui
 
 import (
+	"strings"
 	"time"
 
+	"github.com/Notifiarr/notifiarr/pkg/mnd"
 	"github.com/gen2brain/dlgs"
+	"golift.io/version"
 )
 
+func title(suffix ...string) string {
+	return mnd.Title + " " + version.Version + "-" + version.Revision + " " + strings.Join(suffix, " ")
+}
+
 func now() string {
 	return "\nNow: " + time.Now().Format("Mon Jan 2, 2006 @ 15:04:05 MST")
 }
 
 // Warning wraps dlgs.Warning.
-func Warning(title, msg string) (bool, error) {
+func Warning(msg string) (bool, error) {
 	if !HasGUI() {
 		return true, nil
 	}
 
-	return dlgs.Warning(title, msg+now()) //nolint:wrapcheck
+	return dlgs.Warning(title(), msg+now()) //nolint:wrapcheck
 }
 
 // Error wraps dlgs.Error.
-func Error(title, msg string) (bool, error) {
+func Error(msg string) (bool, error) {
 	if !HasGUI() {
 		return true, nil
 	}
 
-	return dlgs.Error(title, msg+now()) //nolint:wrapcheck
+	return dlgs.Error(title("ERROR"), msg+now()) //nolint:wrapcheck
 }
 
 // Info wraps dlgs.Info.
-func Info(title, msg string) (bool, error) {
+func Info(msg string) (bool, error) {
 	if !HasGUI() {
 		return true, nil
 	}
 
-	return dlgs.Info(title, msg+now()) //nolint:wrapcheck
+	return dlgs.Info(title(), msg+now()) //nolint:wrapcheck
 }
 
 // Entry wraps dlgs.Entry.
-func Entry(title, msg, val string) (string, bool, error) {
+func Entry(msg, val string) (string, bool, error) {
 	if !HasGUI() {
 		return val, true, nil
 	}
 
-	return dlgs.Entry(title, msg+now(), val) //nolint:wrapcheck
+	return dlgs.Entry(title(), msg+now(), val) //nolint:wrapcheck
 }
 
 // Question wraps dlgs.Question.
-func Question(title, text string, defaultCancel bool) (bool, error) {
+func Question(text string, defaultCancel bool) (bool, error) {
 	if !HasGUI() {
 		return true, nil
 	}
 
-	return dlgs.Question(title, text+now(), defaultCancel) //nolint:wrapcheck
+	return dlgs.Question(title(), text+now(), defaultCancel) //nolint:wrapcheck
 }
diff --git a/pkg/website/website.go b/pkg/website/website.go
index e1c751574..c3488d352 100644
--- a/pkg/website/website.go
+++ b/pkg/website/website.go
@@ -54,8 +54,7 @@ func unmarshalResponse(url string, code int, body io.ReadCloser) (*Response, err
 				ErrNon200, url, code, http.StatusText(code), err, buf.String()) //nolint:errorlint
 		}
 
-		return &resp, fmt.Errorf("%w: %s: %d %s",
-			ErrNon200, url, code, http.StatusText(code))
+		return &resp, fmt.Errorf("%w: %s: %d %s", ErrNon200, url, code, http.StatusText(code))
 	}
 
 	if err != nil {