This will extend the user login session auth cookie (session_tokens row in wp_usermeta) when the user is an Administrator and checks the Remember Me checkbox on login. Needed this for admins only, and all posts out there I found only did it for all users, and current_user_can didn't work so used user_can with ID.

extend-wordpress-user-session.php

<?php
/**
 * Extend expiration length of the auth cookie for Administrators when hey check Remember Me
 *
 * @param int $expiration Cookie expiration passed by auth_cookie_expiration() hook
 * @return int 90 days in seconds
 */
function chuck_extend_admins_login_session( $expiration, $user_id, $remember ) {

	if ( $remember && user_can( $user_id, 'manage_options' ) ) {

		$expiration = 7776000; // 90 days in seconds

	}

	return $expiration;

}
add_filter( 'auth_cookie_expiration','chuck_extend_admins_login_session', 10, 3 );