diff --git a/projects/packages/connection/changelog/add-test_blog_token_health b/projects/packages/connection/changelog/add-test_blog_token_health
new file mode 100644
index 000000000000..17ebed61f344
--- /dev/null
+++ b/projects/packages/connection/changelog/add-test_blog_token_health
@@ -0,0 +1,4 @@
+Significance: minor
+Type: added
+
+Add new test for blog token health to support user-less sites
diff --git a/projects/packages/connection/src/class-tokens.php b/projects/packages/connection/src/class-tokens.php
index 730318ecd971..41a8f06364e4 100644
--- a/projects/packages/connection/src/class-tokens.php
+++ b/projects/packages/connection/src/class-tokens.php
@@ -70,6 +70,36 @@ public function validate( $user_id = null ) {
 		return $body ? $body : false;
 	}
 
+	/**
+	 * Perform the API request to validate only the blog.
+	 *
+	 * @return bool|WP_Error Boolean with the test result. WP_Error if test cannot be performed.
+	 */
+	public function validate_blog_token() {
+		$blog_id = Jetpack_Options::get_option( 'id' );
+		if ( ! $blog_id ) {
+			return new WP_Error( 'site_not_registered', 'Site not registered.' );
+		}
+		$url = sprintf(
+			'%s/%s/v%s/%s',
+			Constants::get_constant( 'JETPACK__WPCOM_JSON_API_BASE' ),
+			'wpcom',
+			'2',
+			'sites/' . $blog_id . '/jetpack-token-health/blog'
+		);
+
+		$method   = 'GET';
+		$response = Client::remote_request( compact( 'url', 'method' ) );
+
+		if ( is_wp_error( $response ) || ! wp_remote_retrieve_body( $response ) || 200 !== wp_remote_retrieve_response_code( $response ) ) {
+			return false;
+		}
+
+		$body = json_decode( wp_remote_retrieve_body( $response ), true );
+
+		return is_array( $body ) && isset( $body['is_healthy'] ) && true === $body['is_healthy'];
+	}
+
 	/**
 	 * Obtains the auth token.
 	 *
diff --git a/projects/plugins/jetpack/_inc/lib/debugger/class-jetpack-cxn-tests.php b/projects/plugins/jetpack/_inc/lib/debugger/class-jetpack-cxn-tests.php
index 26b1cc151a34..30ecc893fcaa 100644
--- a/projects/plugins/jetpack/_inc/lib/debugger/class-jetpack-cxn-tests.php
+++ b/projects/plugins/jetpack/_inc/lib/debugger/class-jetpack-cxn-tests.php
@@ -471,17 +471,70 @@ protected function test__identity_crisis() {
 	}
 
 	/**
-	 * Tests blog and current user's token against wp.com's check-token-health endpoint.
+	 * Tests the health of the Connection tokens.
+	 *
+	 * This will always check the blog token health. It will also check the user token health if
+	 * a user is logged in and connected, or if there's a connected owner.
 	 *
 	 * @since 9.0.0
+	 * @since 9.6.0 Checks only blog token if current user not connected or site does not have a connected owner.
 	 *
 	 * @return array Test results.
 	 */
 	protected function test__connection_token_health() {
-		$name = __FUNCTION__;
+		$name    = __FUNCTION__;
+		$m       = new Connection_Manager();
+		$user_id = get_current_user_id();
+
+		// Check if there's a connected logged in user.
+		if ( $user_id && ! $m->is_user_connected( $user_id ) ) {
+				$user_id = false;
+		}
+
+		// If no logged in user to check, let's see if there's a master_user set.
+		if ( ! $user_id ) {
+				$user_id = Jetpack_Options::get_option( 'master_user' );
+			if ( $user_id && ! $m->is_user_connected( $user_id ) ) {
+				return self::connection_failing_test( $name, __( 'Missing token for the connection owner.', 'jetpack' ) );
+			}
+		}
 
-		$m                = new Connection_Manager();
-		$user_id          = get_current_user_id() ? get_current_user_id() : $m->get_connection_owner_id();
+		if ( $user_id ) {
+			return $this->check_tokens_health( $user_id );
+		} else {
+			return $this->check_blog_token_health();
+		}
+	}
+
+	/**
+	 * Tests blog and user's token against wp.com's check-token-health endpoint.
+	 *
+	 * @since 9.6.0
+	 *
+	 * @return array Test results.
+	 */
+	protected function check_blog_token_health() {
+		$name  = 'test__connection_token_health';
+		$valid = ( new Tokens() )->validate_blog_token();
+
+		if ( ! $valid ) {
+			return self::connection_failing_test( $name, __( 'Blog token validation failed.', 'jetpack' ) );
+		} else {
+			return self::passing_test( array( 'name' => $name ) );
+		}
+	}
+
+	/**
+	 * Tests blog token against wp.com's check-token-health endpoint.
+	 *
+	 * @since 9.6.0
+	 *
+	 * @param int $user_id The user ID to check the tokens for.
+	 *
+	 * @return array Test results.
+	 */
+	protected function check_tokens_health( $user_id ) {
+		$name             = 'test__connection_token_health';
 		$validated_tokens = ( new Tokens() )->validate( $user_id );
 
 		if ( ! is_array( $validated_tokens ) || count( array_diff_key( array_flip( array( 'blog_token', 'user_token' ) ), $validated_tokens ) ) ) {
diff --git a/projects/plugins/jetpack/changelog/add-test_blog_token_health b/projects/plugins/jetpack/changelog/add-test_blog_token_health
new file mode 100644
index 000000000000..4260edd04317
--- /dev/null
+++ b/projects/plugins/jetpack/changelog/add-test_blog_token_health
@@ -0,0 +1,4 @@
+Significance: minor
+Type: compat
+
+Add new test for blog token health to support user-less sites