diff --git a/clientupdate/clientupdate.go b/clientupdate/clientupdate.go
index 74942427e..76a849bf1 100644
--- a/clientupdate/clientupdate.go
+++ b/clientupdate/clientupdate.go
@@ -606,11 +606,11 @@ func (up *Updater) updateAlpineLike() (err error) {
 
 	out, err := exec.Command("apk", "update").CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("failed refresh apk repository indexes: %w, output: %q", err, out)
+		return fmt.Errorf("failed refresh apk repository indexes: %w, output:\n%s", err, out)
 	}
 	out, err = exec.Command("apk", "info", "tailscale").CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("failed checking apk for latest tailscale version: %w, output: %q", err, out)
+		return fmt.Errorf("failed checking apk for latest tailscale version: %w, output:\n%s", err, out)
 	}
 	ver, err := parseAlpinePackageVersion(out)
 	if err != nil {
@@ -658,7 +658,7 @@ func (up *Updater) updateMacAppStore() error {
 
 	out, err := exec.Command("open", "https://apps.apple.com/us/app/tailscale/id1475387142").CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("can't open the Tailscale page in App Store: %w, output: %q", err, string(out))
+		return fmt.Errorf("can't open the Tailscale page in App Store: %w, output:\n%s", err, string(out))
 	}
 	return nil
 }
@@ -925,23 +925,29 @@ func (up *Updater) updateFreeBSD() (err error) {
 
 	out, err := exec.Command("pkg", "update").CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("failed refresh pkg repository indexes: %w, output: %q", err, out)
+		return fmt.Errorf("failed refresh pkg repository indexes: %w, output:\n%s", err, out)
 	}
 	out, err = exec.Command("pkg", "rquery", "%v", "tailscale").CombinedOutput()
 	if err != nil {
-		return fmt.Errorf("failed checking pkg for latest tailscale version: %w, output: %q", err, out)
+		return fmt.Errorf("failed checking pkg for latest tailscale version: %w, output:\n%s", err, out)
 	}
 	ver := string(bytes.TrimSpace(out))
 	if !up.confirm(ver) {
 		return nil
 	}
 
-	cmd := exec.Command("pkg", "upgrade", "tailscale")
+	cmd := exec.Command("pkg", "upgrade", "-y", "tailscale")
 	cmd.Stdout = up.Stdout
 	cmd.Stderr = up.Stderr
 	if err := cmd.Run(); err != nil {
 		return fmt.Errorf("failed tailscale update using pkg: %w", err)
 	}
+
+	// pkg does not automatically restart services after upgrade.
+	out, err = exec.Command("service", "tailscaled", "restart").CombinedOutput()
+	if err != nil {
+		return fmt.Errorf("failed to restart tailscaled after update: %w, output:\n%s", err, out)
+	}
 	return nil
 }
 
diff --git a/ipn/ipnlocal/c2n.go b/ipn/ipnlocal/c2n.go
index 6b4aa094a..52184dc60 100644
--- a/ipn/ipnlocal/c2n.go
+++ b/ipn/ipnlocal/c2n.go
@@ -332,24 +332,33 @@ func findCmdTailscale() (string, error) {
 	if err != nil {
 		return "", err
 	}
+	var ts string
 	switch runtime.GOOS {
 	case "linux":
 		if self == "/usr/sbin/tailscaled" || self == "/usr/bin/tailscaled" {
-			return "/usr/bin/tailscale", nil
+			ts = "/usr/bin/tailscale"
 		}
 		if self == "/usr/local/sbin/tailscaled" || self == "/usr/local/bin/tailscaled" {
-			return "/usr/local/bin/tailscale", nil
+			ts = "/usr/local/bin/tailscale"
 		}
-		return "", errors.New("tailscale not found in expected place")
 	case "windows":
-		dir := filepath.Dir(self)
-		ts := filepath.Join(dir, "tailscale.exe")
-		if fi, err := os.Stat(ts); err == nil && fi.Mode().IsRegular() {
-			return ts, nil
+		ts = filepath.Join(filepath.Dir(self), "tailscale.exe")
+	case "freebsd":
+		if self == "/usr/local/bin/tailscaled" {
+			ts = "/usr/local/bin/tailscale"
 		}
-		return "", errors.New("tailscale.exe not found in expected place")
+	default:
+		return "", fmt.Errorf("unsupported OS %v", runtime.GOOS)
 	}
-	return "", fmt.Errorf("unsupported OS %v", runtime.GOOS)
+	if ts != "" && regularFileExists(ts) {
+		return ts, nil
+	}
+	return "", errors.New("tailscale executable not found in expected place")
+}
+
+func regularFileExists(path string) bool {
+	fi, err := os.Stat(path)
+	return err == nil && fi.Mode().IsRegular()
 }
 
 func (b *LocalBackend) handleC2NWoL(w http.ResponseWriter, r *http.Request) {