diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5f67077..df6961e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,10 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+### Fixed
+
+- Gateway status probes (Site Health test, status REST route, settings connection test, `wp pinch status`) fall back to OpenClaw 2.0's `/v1/status` when the legacy `/api/v1/status` path returns 404. OpenClaw 2.0 removed the `/api` route prefix, which made every probe report the gateway unreachable while chat kept working.
+
 ## [3.1.2] - 2026-03-28
 
 Why this matters: Dependabot security and maintenance bumps (wp-env, PHPStan, XML stack) land in one release, and local PHPUnit runs without hand-wiring polyfill paths.
diff --git a/includes/CLI/Status_Command.php b/includes/CLI/Status_Command.php
index 90910ff..2ac65a2 100644
--- a/includes/CLI/Status_Command.php
+++ b/includes/CLI/Status_Command.php
@@ -53,8 +53,8 @@ public static function run( array $args, array $assoc_args ): void {
 		$error_msg = '';
 
 		if ( ! empty( $gateway_url ) && ! empty( $api_token ) ) {
-			$response = wp_remote_get(
-				trailingslashit( $gateway_url ) . 'api/v1/status',
+			$response = \WP_Pinch\Rest\Helpers::gateway_status_request(
+				$gateway_url,
 				array(
 					'timeout' => 10,
 					'headers' => array(
diff --git a/includes/Rest/Helpers.php b/includes/Rest/Helpers.php
index 497f412..045db4c 100644
--- a/includes/Rest/Helpers.php
+++ b/includes/Rest/Helpers.php
@@ -392,4 +392,29 @@ public static function process_sse_buffer( string $buffer ): array {
 		$out = implode( "\n", $output );
 		return array( '' !== $out ? $out . "\n" : '', $carry ?? '' );
 	}
+
+	/**
+	 * GET the gateway status endpoint, tolerating both path generations.
+	 *
+	 * OpenClaw 1.x serves the status probe at /api/v1/status; OpenClaw 2.0
+	 * removed the /api route prefix and serves /v1/status. Probe the legacy
+	 * path first (no behavior change for 1.x gateways) and retry the 2.0
+	 * path only on a 404.
+	 *
+	 * @param string $gateway_url Gateway base URL.
+	 * @param array  $args        Request args (timeout, auth header).
+	 * @param bool   $safe        Use wp_safe_remote_get() (SSRF-hardened) instead
+	 *                            of wp_remote_get(); matches each caller's
+	 *                            previous transport.
+	 * @return array|\WP_Error HTTP response array or WP_Error.
+	 */
+	public static function gateway_status_request( string $gateway_url, array $args, bool $safe = false ) {
+		$base     = trailingslashit( $gateway_url );
+		$get      = $safe ? 'wp_safe_remote_get' : 'wp_remote_get';
+		$response = $get( $base . 'api/v1/status', $args );
+		if ( ! is_wp_error( $response ) && 404 === (int) wp_remote_retrieve_response_code( $response ) ) {
+			$response = $get( $base . 'v1/status', $args );
+		}
+		return $response;
+	}
 }
diff --git a/includes/Rest/Status.php b/includes/Rest/Status.php
index 0961b04..581c906 100644
--- a/includes/Rest/Status.php
+++ b/includes/Rest/Status.php
@@ -68,12 +68,13 @@ public static function handle_status( \WP_REST_Request $request ): \WP_REST_Resp
 		if ( $result['configured'] ) {
 			$status_url = trailingslashit( $gateway_url ) . 'api/v1/status';
 			if ( wp_http_validate_url( $status_url ) ) {
-				$response = wp_safe_remote_get(
-					$status_url,
+				$response = Helpers::gateway_status_request(
+					$gateway_url,
 					array(
 						'timeout' => 5,
 						'headers' => array( 'Authorization' => 'Bearer ' . $api_token ),
-					)
+					),
+					true
 				);
 			} else {
 				$response = new \WP_Error( 'invalid_gateway', __( 'Gateway URL failed security validation.', 'wp-pinch' ) );
diff --git a/includes/Settings/Settings_Admin_Pages_Trait.php b/includes/Settings/Settings_Admin_Pages_Trait.php
index 5a462a4..4f4c79d 100644
--- a/includes/Settings/Settings_Admin_Pages_Trait.php
+++ b/includes/Settings/Settings_Admin_Pages_Trait.php
@@ -138,14 +138,15 @@ public static function ajax_test_connection(): void {
 			wp_send_json_error( __( 'Gateway URL failed security validation. Use a public HTTP or HTTPS URL.', 'wp-pinch' ) );
 		}
 
-		$response = wp_safe_remote_get(
-			$status_url,
+		$response = Rest\Helpers::gateway_status_request(
+			$url,
 			array(
 				'timeout' => 10,
 				'headers' => array(
 					'Authorization' => 'Bearer ' . $token,
 				),
-			)
+			),
+			true
 		);
 
 		if ( is_wp_error( $response ) ) {
diff --git a/includes/class-site-health.php b/includes/class-site-health.php
index 51c2589..f8a4c97 100644
--- a/includes/class-site-health.php
+++ b/includes/class-site-health.php
@@ -217,8 +217,8 @@ public static function test_gateway_connectivity(): array {
 			return $result;
 		}
 
-		$response = wp_remote_get(
-			trailingslashit( $gateway_url ) . 'api/v1/status',
+		$response = Rest\Helpers::gateway_status_request(
+			$gateway_url,
 			array(
 				'timeout' => 10,
 				'headers' => array(