diff --git a/includes/class-logger.php b/includes/class-logger.php
index 4bf48a977f..6a31567744 100644
--- a/includes/class-logger.php
+++ b/includes/class-logger.php
@@ -76,4 +76,41 @@ private static function get_pid() {
 	public static function error( $payload, $header = 'NEWSPACK' ) {
 		return self::log( $payload, $header, 'error' );
 	}
+
+	/**
+	 * A logger for newspack manager logging.
+	 *
+	 * @param string $code      The log code (i.e. newspack_google_login).
+	 * @param string $message   The message to log.
+	 * @param array  $data      The data to log.
+	 *      Optional. Additional parameters.
+	 *      @type string $user_email The current users email address.
+	 *      @type file   $file       The name of the file to write the local log to.
+	 * @param string $type      The type of log. Defaults to 'error'.
+	 * @param string $log_level The Log level.
+	 */
+	public static function newspack_log( $code, $message, $data, $type = 'error', $log_level = 2 ) {
+		$email = '';
+		if ( isset( $data['user_email'] ) ) {
+			$email = $data['user_email'];
+			unset( $data['user_email'] );
+		}
+		$file = $code;
+		if ( isset( $data['file'] ) ) {
+			$file = $data['file'];
+			unset( $data['file'] );
+		}
+		do_action(
+			'newspack_log',
+			$code,
+			$message,
+			[
+				'type'       => $type,
+				'data'       => $data,
+				'user_email' => $email,
+				'file'       => $file,
+				'log_level'  => $log_level,
+			]
+		);
+	}
 }
diff --git a/includes/class-newspack.php b/includes/class-newspack.php
index 0be50a7634..8f844d245c 100644
--- a/includes/class-newspack.php
+++ b/includes/class-newspack.php
@@ -155,6 +155,7 @@ private function includes() {
 		include_once NEWSPACK_ABSPATH . 'includes/plugins/class-jetpack.php';
 		include_once NEWSPACK_ABSPATH . 'includes/plugins/class-gravityforms.php';
 		include_once NEWSPACK_ABSPATH . 'includes/plugins/google-site-kit/class-googlesitekit.php';
+		include_once NEWSPACK_ABSPATH . 'includes/plugins/google-site-kit/class-googlesitekit-logger.php';
 		include_once NEWSPACK_ABSPATH . 'includes/plugins/class-mailchimp-for-woocommerce.php';
 		include_once NEWSPACK_ABSPATH . 'includes/plugins/class-onesignal.php';
 		include_once NEWSPACK_ABSPATH . 'includes/plugins/class-organic-profile-block.php';
diff --git a/includes/plugins/google-site-kit/class-googlesitekit-logger.php b/includes/plugins/google-site-kit/class-googlesitekit-logger.php
new file mode 100644
index 0000000000..4c421f4868
--- /dev/null
+++ b/includes/plugins/google-site-kit/class-googlesitekit-logger.php
@@ -0,0 +1,141 @@
+<?php
+/**
+ * Google Site Kit Logger class.
+ *
+ * @package Newspack
+ */
+
+namespace Newspack;
+
+use Google\Site_Kit\Core\Authentication\Has_Connected_Admins;
+use Google\Site_Kit\Core\Authentication\Disconnected_Reason;
+
+defined( 'ABSPATH' ) || exit;
+
+/**
+ * Main class.
+ */
+class GoogleSiteKit_Logger {
+	/**
+	 * The hook name for site kit disconnection logger cron job.
+	 */
+	const CRON_HOOK = 'newspack_googlesitekit_disconnection_logger';
+
+	/**
+	 * The log code for disconnections.
+	 */
+	const LOG_CODE_DISCONNECTED = 'newspack_googlesitekit_disconnected';
+
+	/**
+	 * Initialize hooks and filters.
+	 */
+	public static function init() {
+		if ( GoogleSiteKit::is_active() ) {
+			add_action( 'admin_init', [ __CLASS__, 'cron_init' ] );
+			add_action( 'delete_option_' . self::get_sitekit_ga4_has_connected_admin_option_name(), [ __CLASS__, 'log_disconnected_admins' ] );
+			add_filter( 'update_user_metadata', [ __CLASS__, 'maybe_log_disconnected_reason' ], 10, 5 );
+			add_action( self::CRON_HOOK, [ __CLASS__, 'handle_cron_event' ] );
+		}
+	}
+
+	/**
+	 * Schedule cron job to check for site kit connection. If the connection is lost we log it.
+	 */
+	public static function cron_init() {
+		register_deactivation_hook( NEWSPACK_PLUGIN_FILE, [ __CLASS__, 'cron_deactivate' ] );
+
+		if ( defined( 'NEWSPACK_CRON_DISABLE' ) && is_array( NEWSPACK_CRON_DISABLE ) && in_array( self::CRON_HOOK, NEWSPACK_CRON_DISABLE, true ) ) {
+			self::cron_deactivate();
+		} elseif ( ! wp_next_scheduled( self::CRON_HOOK ) ) {
+			wp_schedule_event( time(), 'daily', self::CRON_HOOK );
+		}
+	}
+
+	/**
+	 * Deactivate the cron job.
+	 */
+	public static function cron_deactivate() {
+		wp_clear_scheduled_hook( self::CRON_HOOK );
+	}
+
+
+	/**
+	 * Get the name of the option under which Site Kit's GA4 has connected admin flag is stored.
+	 */
+	private static function get_sitekit_ga4_has_connected_admin_option_name() {
+		if ( class_exists( 'Google\Site_Kit\Core\Authentication\Has_Connected_Admins' ) ) {
+			return Has_Connected_Admins::OPTION;
+		}
+		return 'googlesitekit_has_connected_admins';
+	}
+
+	/**
+	 * Get the name of the option under which Site Kit's disconnected reason is stored.
+	 */
+	private static function get_sitekit_ga4_disconnected_reason_option_name() {
+		if ( class_exists( 'Google\Site_Kit\Core\Authentication\Disconnected_Reason' ) ) {
+			return Disconnected_Reason::OPTION;
+		}
+		return 'googlesitekit_disconnected_reason';
+	}
+
+	/**
+	 * Logs disconnect reason when user meta update is triggered.
+	 *
+	 * @param bool   $check      Whether to update metadata.
+	 * @param int    $object_id  Object ID.
+	 * @param string $meta_key   Meta key.
+	 * @param mixed  $meta_value Meta value.
+	 * @param mixed  $prev_value Previous meta value.
+	 */
+	public static function maybe_log_disconnected_reason( $check, $object_id, $meta_key, $meta_value, $prev_value ) {
+		if (
+			// The meta key will have the database prefixed so we need to use str_contains.
+			str_contains( $meta_key, self::get_sitekit_ga4_disconnected_reason_option_name() ) &&
+			$meta_value !== $prev_value
+		) {
+			self::log(
+				self::LOG_CODE_DISCONNECTED,
+				'Google Site Kit has been disconnected with reason ' . $meta_value
+			);
+		}
+		return $check;
+	}
+
+	/**
+	 * Logs when cron event runs and all admins are disconnected.
+	 */
+	public static function handle_cron_event() {
+		if ( ! get_option( self::get_sitekit_ga4_has_connected_admin_option_name(), false ) ) {
+			self::log( self::LOG_CODE_DISCONNECTED, 'No active Google Site Kit connections found', false, 3 );
+		}
+	}
+
+	/**
+	 * Log when all admins are disconnected.
+	 */
+	public static function log_disconnected_admins() {
+		self::log( self::LOG_CODE_DISCONNECTED, 'Google Site Kit has been disconnected for all admins' );
+	}
+
+	/**
+	 * Main site kit logger.
+	 *
+	 * @param string $code      The code for the log.
+	 * @param string $message   The message to log. Optional.
+	 * @param bool   $backtrace Whether to include a backtrace.
+	 * @param int    $log_level The log level.
+	 */
+	private static function log( $code, $message, $backtrace = true, $log_level = 2 ) {
+		$data = [
+			'file'       => $code,
+			'user_email' => wp_get_current_user()->user_email,
+		];
+		if ( $backtrace ) {
+			$e                 = new \Exception();
+			$data['backtrace'] = $e->getTraceAsString();
+		}
+		Logger::newspack_log( $code, $message, $data, 'error', $log_level );
+	}
+}
+GoogleSiteKit_Logger::init();
diff --git a/includes/plugins/google-site-kit/class-googlesitekit.php b/includes/plugins/google-site-kit/class-googlesitekit.php
index 704740aec2..e6a25e50c2 100644
--- a/includes/plugins/google-site-kit/class-googlesitekit.php
+++ b/includes/plugins/google-site-kit/class-googlesitekit.php
@@ -70,6 +70,15 @@ public static function insert_ga4_analytics() {
 		<?php
 	}
 
+	/**
+	 * Get whether Site Kit is active.
+	 *
+	 * @return bool Whether Site Kit is active.
+	 */
+	public static function is_active() {
+		return class_exists( 'Google\Site_Kit\Core\Modules\Module' );
+	}
+
 	/**
 	 * Get whether the current user is connected.
 	 *
@@ -111,7 +120,7 @@ private static function get_sitekit_ga4_settings() {
 	 * Fetch data for the GA account data and set up GA4.
 	 */
 	public static function setup_sitekit_ga4() {
-		if ( ! class_exists( 'Google\Site_Kit\Core\Modules\Module' ) ) {
+		if ( ! self::is_active() ) {
 			return;
 		}
 		require_once NEWSPACK_ABSPATH . 'includes/plugins/google-site-kit/class-googlesitekitanalytics.php';