diff --git a/inc/class-sunrise.php b/inc/class-sunrise.php
index 919f4be52..1e98bb74d 100644
--- a/inc/class-sunrise.php
+++ b/inc/class-sunrise.php
@@ -335,7 +335,9 @@ public static function load(): void {
 			$security_mode = (bool) (int) wu_get_setting_early('security_mode');
 
 			if ($security_mode) {
-				if (wu_get_isset($_GET, 'wu_secure') === wu_get_security_mode_key()) { // phpcs:ignore WordPress.Security.NonceVerification
+				$provided_key = wu_get_isset($_GET, 'wu_secure'); // phpcs:ignore WordPress.Security.NonceVerification
+
+				if (is_string($provided_key) && hash_equals(wu_get_security_mode_key(false), $provided_key)) {
 					wu_save_setting_early('security_mode', false);
 				} else {
 					/**
diff --git a/inc/functions/sunrise.php b/inc/functions/sunrise.php
index d016695a2..08e3e3b3c 100644
--- a/inc/functions/sunrise.php
+++ b/inc/functions/sunrise.php
@@ -72,11 +72,50 @@ function wu_save_setting_early($key, $value) {
 }
 
 /**
- * Get the security mode key used to disable security mode
+ * Get the security mode key used to disable security mode.
+ *
+ * This key is exposed in an unauthenticated query string (?wu_secure=KEY) that
+ * turns the network-wide recovery "security mode" off, so it must be
+ * unpredictable. It used to be substr(md5(admin_email), 0, 6) — only ~24 bits
+ * and derived from a frequently public/guessable value, which an attacker could
+ * compute or brute-force. We now use a high-entropy random secret generated once
+ * and stored as a network option when the key is displayed to admins.
+ * random_bytes() is used (not wp_generate_password) because this runs from
+ * sunrise, before pluggable.php is loaded. Sunrise validation does not generate
+ * a new key while security mode is already active; if a random key has not been
+ * persisted yet, the legacy derived key remains valid until an admin loads the
+ * settings screen and sees the new random recovery URL.
  *
  * @since 2.0.20
+ *
+ * @param bool $generate Whether to generate and persist a random key when missing.
+ * @return string
+ */
+function wu_get_security_mode_key($generate = true): string {
+
+	$key = (string) get_network_option(null, 'wu_security_mode_key', '');
+
+	if ('' === $key) {
+		if (! $generate) {
+			return wu_get_legacy_security_mode_key();
+		}
+
+		$key = bin2hex(random_bytes(16));
+
+		update_network_option(null, 'wu_security_mode_key', $key);
+	}
+
+	return $key;
+}
+
+/**
+ * Get the legacy security mode key used before high-entropy keys were persisted.
+ *
+ * @since 2.0.20
+ *
+ * @return string
  */
-function wu_get_security_mode_key(): string {
+function wu_get_legacy_security_mode_key(): string {
 
 	$hash = md5((string) get_network_option(null, 'admin_email'));
 
diff --git a/tests/WP_Ultimo/Functions/Sunrise_Functions_Test.php b/tests/WP_Ultimo/Functions/Sunrise_Functions_Test.php
index f20f15121..573272972 100644
--- a/tests/WP_Ultimo/Functions/Sunrise_Functions_Test.php
+++ b/tests/WP_Ultimo/Functions/Sunrise_Functions_Test.php
@@ -101,14 +101,16 @@ public function test_save_setting_early_stores_value(): void {
 	}
 
 	/**
-	 * Test wu_get_security_mode_key returns a 6-character string.
+	 * Test wu_get_security_mode_key returns a high-entropy string.
 	 */
-	public function test_get_security_mode_key_returns_six_char_string(): void {
+	public function test_get_security_mode_key_returns_high_entropy_string(): void {
+
+		delete_network_option(null, 'wu_security_mode_key');
 
 		$key = wu_get_security_mode_key();
 
 		$this->assertIsString($key);
-		$this->assertSame(6, strlen($key));
+		$this->assertSame(32, strlen($key));
 	}
 
 	/**
@@ -116,15 +118,19 @@ public function test_get_security_mode_key_returns_six_char_string(): void {
 	 */
 	public function test_get_security_mode_key_returns_hex_characters(): void {
 
+		delete_network_option(null, 'wu_security_mode_key');
+
 		$key = wu_get_security_mode_key();
 
-		$this->assertMatchesRegularExpression('/^[0-9a-f]{6}$/', $key);
+		$this->assertMatchesRegularExpression('/^[0-9a-f]{32}$/', $key);
 	}
 
 	/**
-	 * Test wu_get_security_mode_key is deterministic for same admin email.
+	 * Test wu_get_security_mode_key is stable after generation.
 	 */
-	public function test_get_security_mode_key_is_deterministic(): void {
+	public function test_get_security_mode_key_is_stable_after_generation(): void {
+
+		delete_network_option(null, 'wu_security_mode_key');
 
 		$key1 = wu_get_security_mode_key();
 		$key2 = wu_get_security_mode_key();
@@ -132,6 +138,20 @@ public function test_get_security_mode_key_is_deterministic(): void {
 		$this->assertSame($key1, $key2);
 	}
 
+	/**
+	 * Test wu_get_security_mode_key can preserve the legacy key without rotating.
+	 */
+	public function test_get_security_mode_key_without_generation_returns_legacy_key(): void {
+
+		delete_network_option(null, 'wu_security_mode_key');
+
+		$expected = substr(md5((string) get_network_option(null, 'admin_email')), 0, 6);
+		$key      = wu_get_security_mode_key(false);
+
+		$this->assertSame($expected, $key);
+		$this->assertSame('', get_network_option(null, 'wu_security_mode_key', ''));
+	}
+
 	/**
 	 * Test wu_kses_data returns string.
 	 */