diff --git a/projects/packages/connection/src/class-manager.php b/projects/packages/connection/src/class-manager.php
index c2f8c751c11f0..b6676644b6a62 100644
--- a/projects/packages/connection/src/class-manager.php
+++ b/projects/packages/connection/src/class-manager.php
@@ -147,8 +147,17 @@ public static function configure() {
 		add_action( 'deleted_user', array( $manager, 'disconnect_user_force' ), 9, 1 );
 		add_action( 'remove_user_from_blog', array( $manager, 'disconnect_user_force' ), 9, 1 );
 
+		// Force is_connected() to recompute after important actions.
 		add_action( 'jetpack_site_registered', array( $manager, 'reset_connection_status' ) );
 		add_action( 'jetpack_site_disconnected', array( $manager, 'reset_connection_status' ) );
+		add_action( 'jetpack_sync_register_user', array( $manager, 'reset_connection_status' ) );
+		add_action( 'pre_update_jetpack_option_id', array( $manager, 'reset_connection_status' ) );
+		add_action( 'pre_update_jetpack_blog_token', array( $manager, 'reset_connection_status' ) );
+		add_action( 'pre_update_jetpack_user_token', array( $manager, 'reset_connection_status' ) );
+		add_action( 'pre_update_jetpack_user_tokens', array( $manager, 'reset_connection_status' ) );
+		add_action( 'update_option', array( $manager, 'maybe_reset_connection_status' ), 10, 1 );
+		add_action( 'add_option', array( $manager, 'maybe_reset_connection_status' ), 10, 1 );
+		add_action( 'delete_option', array( $manager, 'maybe_reset_connection_status' ), 10, 1 );
 
 		// Set up package version hook.
 		add_filter( 'jetpack_package_versions', __NAMESPACE__ . '\Package_Version::send_package_version_to_tracker' );
@@ -629,6 +638,22 @@ public function reset_connection_status() {
 		self::$is_connected = null;
 	}
 
+	/**
+	 * Resets the memoized connection status if jetpack_private_options is updated.
+	 *
+	 * Ideally, we would only do this on certain "sub" options stored inside
+	 * jetpack_private_options, but delete_option() -> delete_grouped_option()
+	 * provides us no hook to detect which options are being deleted.
+	 *
+	 * @param string $option The option name.
+	 */
+	public function maybe_reset_connection_status( $option ) {
+		$reset_options = array( 'jetpack_private_options' );
+		if ( in_array( $option, $reset_options, true ) ) {
+			self::$is_connected = null;
+		}
+	}
+
 	/**
 	 * Returns true if the site has at least one connected administrator.
 	 *