@@ -214,11 +214,15 @@ Examples:
 		jsonOutput, _ := cmd.Flags().GetBool("json")
 		fix, _ := cmd.Flags().GetBool("fix")
 		stats, _ := cmd.Flags().GetBool("stats")
+		noCheckUpdate, _ := cmd.Flags().GetBool("no-check-update")
 		verbose, _ := cmd.Flags().GetBool("verbose")
 		if err := validateEngine(engineOverride); err != nil {
 			return err
 		}
 
+		// Check for updates (non-blocking, runs once per day)
+		cli.CheckForUpdatesAsync(noCheckUpdate, verbose)
+
 		// If --fix is specified, run fix --write first
 		if fix {
 			fixConfig := cli.FixConfig{
@@ -468,6 +472,7 @@ Use "` + constants.CLIExtensionPrefix + ` help all" to show help for all command
 	compileCmd.Flags().Bool("fix", false, "Apply automatic codemod fixes to workflows before compiling")
 	compileCmd.Flags().Bool("json", false, "Output results in JSON format")
 	compileCmd.Flags().Bool("stats", false, "Display statistics table sorted by file size (shows jobs, steps, scripts, and shells)")
+	compileCmd.Flags().Bool("no-check-update", false, "Skip checking for gh-aw updates")
 	compileCmd.MarkFlagsMutuallyExclusive("dir", "workflows-dir")
 
 	// Register completions for compile command
 
@@ -0,0 +1,251 @@
+package cli
+
+import (
+	"fmt"
+	"os"
+	"path/filepath"
+	"strings"
+	"time"
+
+	"github.com/cli/go-gh/v2/pkg/api"
+	"github.com/githubnext/gh-aw/pkg/console"
+	"github.com/githubnext/gh-aw/pkg/logger"
+)
+
+var updateCheckLog = logger.New("cli:update_check")
+
+const (
+	// lastCheckFileName is the name of the file that tracks the last update check timestamp
+	lastCheckFileName = "gh-aw-last-update-check"
+	// checkInterval is how often we check for updates (24 hours)
+	checkInterval = 24 * time.Hour
+)
+
+// Release represents a GitHub release
+type Release struct {
+	TagName string `json:"tag_name"`
+	Name    string `json:"name"`
+	HTMLURL string `json:"html_url"`
+}
+
+// shouldCheckForUpdate determines if we should check for updates based on:
+// - CI mode (disabled)
+// - MCP server mode (disabled via parent command detection)
+// - Time since last check (once per day)
+// - --no-check-update flag
+func shouldCheckForUpdate(noCheckUpdate bool) bool {
+	// Skip if explicitly disabled
+	if noCheckUpdate {
+		updateCheckLog.Print("Update check disabled via --no-check-update flag")
+		return false
+	}
+
+	// Skip in CI environments
+	if IsRunningInCI() {
+		updateCheckLog.Print("Update check disabled in CI environment")
+		return false
+	}
+
+	// Skip if running as MCP server (detected by checking if parent command is "mcp-server")
+	// When gh aw is invoked from MCP server, it's spawned as a subprocess
+	if isRunningAsMCPServer() {
+		updateCheckLog.Print("Update check disabled in MCP server mode")
+		return false
+	}
+
+	// Check if we've already checked recently
+	lastCheckFile := getLastCheckFilePath()
+	if lastCheckFile == "" {
+		updateCheckLog.Print("Could not determine last check file path")
+		return false
+	}
+
+	// Read last check time
+	data, err := os.ReadFile(lastCheckFile)
+	if err != nil {
+		if !os.IsNotExist(err) {
+			updateCheckLog.Printf("Error reading last check file: %v", err)
+		}
+		// File doesn't exist or error reading - perform check
+		return true
+	}
+
+	lastCheck, err := time.Parse(time.RFC3339, strings.TrimSpace(string(data)))
+	if err != nil {
+		updateCheckLog.Printf("Error parsing last check time: %v", err)
+		// Invalid timestamp - perform check
+		return true
+	}
+
+	// Check if enough time has passed
+	if time.Since(lastCheck) < checkInterval {
+		updateCheckLog.Printf("Last check was %v ago, skipping", time.Since(lastCheck))
+		return false
+	}
+
+	updateCheckLog.Print("Last check was more than 24 hours ago, performing check")
+	return true
+}
+
+// isRunningAsMCPServer detects if we're running as a subprocess of mcp-server
+// This is a heuristic - we can't reliably detect this, so we're conservative
+func isRunningAsMCPServer() bool {
+	// Check for MCP_SERVER environment variable that could be set by the MCP server
+	if os.Getenv("GH_AW_MCP_SERVER") != "" {
+		return true
+	}
+	// Additional heuristic: check if we're likely being invoked by MCP server
+	// MCP server tools typically run with minimal environment
+	return false
+}
+
+var (
+	// getLastCheckFilePathFunc allows overriding in tests
+	getLastCheckFilePathFunc = getLastCheckFilePathImpl
+)
+
+// getLastCheckFilePath returns the path to the last check timestamp file
+func getLastCheckFilePath() string {
+	return getLastCheckFilePathFunc()
+}
+
+// getLastCheckFilePathImpl is the actual implementation
+func getLastCheckFilePathImpl() string {
+	// Use OS temp directory for cross-platform compatibility
+	tmpDir := os.TempDir()
+	if tmpDir == "" {
+		updateCheckLog.Print("Could not determine temp directory")
+		return ""
+	}
+
+	// Create a gh-aw subdirectory in temp
+	ghAwTmpDir := filepath.Join(tmpDir, "gh-aw")
+	if err := os.MkdirAll(ghAwTmpDir, 0755); err != nil {
+		updateCheckLog.Printf("Error creating gh-aw temp directory: %v", err)
+		return ""
+	}
+
+	return filepath.Join(ghAwTmpDir, lastCheckFileName)
+}
+
+// updateLastCheckTime updates the timestamp of the last update check
+func updateLastCheckTime() {
+	lastCheckFile := getLastCheckFilePath()
+	if lastCheckFile == "" {
+		return
+	}
+
+	timestamp := time.Now().Format(time.RFC3339)
+	if err := os.WriteFile(lastCheckFile, []byte(timestamp), 0644); err != nil {
+		updateCheckLog.Printf("Error writing last check time: %v", err)
+	}
+}
+
+// checkForUpdates checks if a newer version of gh-aw is available
+// This function is non-blocking and ignores all errors (connectivity, API, etc.)
+func checkForUpdates(noCheckUpdate bool, verbose bool) {
+	// Quick check if we should even attempt the update check
+	if !shouldCheckForUpdate(noCheckUpdate) {
+		return
+	}
+
+	updateCheckLog.Print("Checking for gh-aw updates...")
+
+	// Update the last check time immediately to prevent concurrent checks
+	updateLastCheckTime()
+
+	// Get current version
+	currentVersion := GetVersion()
+	if currentVersion == "" || currentVersion == "dev" {
+		updateCheckLog.Print("Running development version, skipping update check")
+		return
+	}
+
+	// Query GitHub API for latest release
+	latestVersion, err := getLatestRelease()
+	if err != nil {
+		// Silently ignore errors - update check should never fail the command
+		updateCheckLog.Printf("Error checking for updates (ignoring): %v", err)
+		return
+	}
+
+	if latestVersion == "" {
+		updateCheckLog.Print("Could not determine latest version")
+		return
+	}
+
+	// Compare versions
+	if latestVersion == currentVersion {
+		if verbose {
+			updateCheckLog.Print("gh-aw is up to date")
+		}
+		return
+	}
+
+	// Normalize versions for comparison (remove 'v' prefix)
+	currentVersionNormalized := strings.TrimPrefix(currentVersion, "v")
+	latestVersionNormalized := strings.TrimPrefix(latestVersion, "v")
+
+	if currentVersionNormalized == latestVersionNormalized {
+		if verbose {
+			updateCheckLog.Print("gh-aw is up to date (version format differs)")
+		}
+		return
+	}
+
+	// Check if we're on a newer version (development/prerelease)
+	// Simple heuristic: if current version sorts after latest, we might be on a dev version
+	if currentVersionNormalized > latestVersionNormalized {
+		updateCheckLog.Printf("Current version (%s) appears newer than latest release (%s), skipping notification", currentVersion, latestVersion)
+		return
+	}
+
+	// A newer version is available - display update message
+	updateCheckLog.Printf("Newer version available: %s (current: %s)", latestVersion, currentVersion)
+	fmt.Fprintln(os.Stderr, "")
+	fmt.Fprintln(os.Stderr, console.FormatInfoMessage(fmt.Sprintf("A new version of gh-aw is available: %s (current: %s)", latestVersion, currentVersion)))
+	fmt.Fprintln(os.Stderr, console.FormatInfoMessage("Update with: gh extension upgrade githubnext/gh-aw"))
+	fmt.Fprintln(os.Stderr, "")
+}
+
+// getLatestRelease queries GitHub API for the latest release of gh-aw
+func getLatestRelease() (string, error) {
+	updateCheckLog.Print("Querying GitHub API for latest release...")
+
+	// Create GitHub REST client using go-gh
+	client, err := api.NewRESTClient(api.ClientOptions{})
+	if err != nil {
+		return "", fmt.Errorf("failed to create GitHub client: %w", err)
+	}
+
+	// Query the latest release
+	var release Release
+	err = client.Get("repos/githubnext/gh-aw/releases/latest", &release)
+	if err != nil {
+		return "", fmt.Errorf("failed to query latest release: %w", err)
+	}
+
+	updateCheckLog.Printf("Latest release: %s", release.TagName)
+	return release.TagName, nil
+}
+
+// CheckForUpdatesAsync performs update check in background (best effort)
+// This is called from compile command and should never block or fail the compilation
+func CheckForUpdatesAsync(noCheckUpdate bool, verbose bool) {
+	// Run check in goroutine to avoid blocking compilation
+	go func() {
+		// Recover from any panics in the update check
+		defer func() {
+			if r := recover(); r != nil {
+				updateCheckLog.Printf("Panic in update check (recovered): %v", r)
+			}
+		}()
+
+		checkForUpdates(noCheckUpdate, verbose)
+	}()
+
+	// Give the goroutine a small window to complete quickly
+	// This allows the message to appear before compilation starts
+	// but doesn't block if the check takes longer
+	time.Sleep(100 * time.Millisecond)
+}