diff --git a/inc/checkout/class-checkout.php b/inc/checkout/class-checkout.php
index e47eb9e30..f6aa55c96 100644
--- a/inc/checkout/class-checkout.php
+++ b/inc/checkout/class-checkout.php
@@ -989,7 +989,11 @@ public function process_order() {
 		 * let's check if the user is logged in,
 		 * and if not, let's do that.
 		 */
-		$this->login_customer_after_checkout();
+		$login_result = $this->login_customer_after_checkout();
+
+		if (is_wp_error($login_result)) {
+			return $login_result;
+		}
 
 		/*
 		 * Action time.
@@ -2402,7 +2406,7 @@ protected function form_has_auto_generate_password(): bool {
 	 * just created in this very request and the credential is not available.
 	 *
 	 * @since 2.6.0
-	 * @return void
+	 * @return \WP_Error|null
 	 */
 	protected function login_customer_after_checkout() {
 
@@ -2426,7 +2430,24 @@ protected function login_customer_after_checkout() {
 			);
 
 			// Sign in the user as if they used the login form.
-			wp_signon($user_credentials, is_ssl());
+			$signed_in_user = wp_signon($user_credentials, is_ssl());
+
+			if (is_wp_error($signed_in_user)) {
+				$login_error_message = wp_strip_all_tags($signed_in_user->get_error_message());
+
+				if (empty($login_error_message)) {
+					$login_error_message = __('Unknown login error.', 'ultimate-multisite');
+				}
+
+				return new \WP_Error(
+					'checkout_login_failed',
+					sprintf(
+						/* translators: %s is the login failure message returned by WordPress or another plugin. */
+						__('We could not log you in automatically during checkout. Please try again or contact support before continuing. Login error: %s', 'ultimate-multisite'),
+						$login_error_message
+					)
+				);
+			}
 
 			return;
 		}
diff --git a/tests/WP_Ultimo/Checkout/Checkout_Test.php b/tests/WP_Ultimo/Checkout/Checkout_Test.php
index 155c99963..e3f7ca921 100644
--- a/tests/WP_Ultimo/Checkout/Checkout_Test.php
+++ b/tests/WP_Ultimo/Checkout/Checkout_Test.php
@@ -5010,7 +5010,7 @@ public function test_login_customer_after_checkout_noop_when_logged_in(): void {
 		$method     = $this->get_login_method($reflection);
 
 		$login_fired = false;
-		add_action('wp_login', function() use (&$login_fired) {
+		add_action('wp_login', function () use (&$login_fired) {
 			$login_fired = true;
 		});
 
@@ -5128,7 +5128,7 @@ public function test_login_customer_after_checkout_with_password_fires_wp_login(
 		$_REQUEST['password'] = $password;
 
 		$login_fired = false;
-		add_action('wp_login', function() use (&$login_fired) {
+		add_action('wp_login', function () use (&$login_fired) {
 			$login_fired = true;
 		});
 
@@ -5147,6 +5147,69 @@ public function test_login_customer_after_checkout_with_password_fires_wp_login(
 		wp_delete_user($user_id);
 	}
 
+	/**
+	 * Test login_customer_after_checkout returns a visible error when wp_signon fails.
+	 *
+	 * Security plugins can hook into the normal WordPress authentication flow and
+	 * reject the credential round-trip. Checkout must stop instead of silently
+	 * handing the customer to a payment gateway while logged out.
+	 */
+	public function test_login_customer_after_checkout_with_password_returns_error_when_signon_fails(): void {
+
+		$unique   = uniqid('badpw_', true);
+		$password = 'TestP@ssw0rd!';
+		$user_id  = self::factory()->user->create([
+			'user_login' => $unique,
+			'user_pass'  => $password,
+			'user_email' => $unique . '@example.com',
+		]);
+
+		wp_set_current_user(0);
+		wp_clear_auth_cookie();
+
+		$customer = wu_create_customer([
+			'user_id'  => $user_id,
+			'username' => $unique,
+			'email'    => $unique . '@example.com',
+		]);
+
+		if (is_wp_error($customer)) {
+			require_once ABSPATH . 'wp-admin/includes/user.php';
+			wp_delete_user($user_id);
+			$this->markTestSkipped('Customer creation failed: ' . $customer->get_error_message());
+		}
+
+		$checkout   = Checkout::get_instance();
+		$reflection = new \ReflectionClass($checkout);
+
+		$this->inject_customer($checkout, $reflection, $customer);
+		$this->ensure_session($checkout);
+
+		$_REQUEST['password'] = 'WrongP@ssw0rd!';
+
+		$login_fired = false;
+		add_action('wp_login', function () use (&$login_fired) {
+			$login_fired = true;
+		});
+
+		$method = $this->get_login_method($reflection);
+		$result = $method->invoke($checkout);
+
+		remove_all_actions('wp_login');
+		unset($_REQUEST['password']);
+
+		$this->assertWPError($result);
+		$this->assertSame('checkout_login_failed', $result->get_error_code());
+		$this->assertStringContainsString('Login error:', $result->get_error_message());
+		$this->assertFalse($login_fired, 'wp_login must not fire when wp_signon returns an error');
+
+		// Cleanup.
+		wp_set_current_user(0);
+		$customer->delete();
+		require_once ABSPATH . 'wp-admin/includes/user.php';
+		wp_delete_user($user_id);
+	}
+
 	/**
 	 * Test login_customer_after_checkout handles a customer with user_id = 0 gracefully.
 	 *