The Prestwood Ping Server automates the monitoring of web sites and ftp sites by issuing ping or HTTP requests on regular intervals. It is an ideal application for server farms, large web sites spanning multiple domains, online game servers, download file servers, or any enterprise that spans multiple internet addresses. The user can dictate how often a site is pinged, and in the event of a timeout or DNS error, the delay interval prior to a ping retry attempt. The user can also dictate how many retries to issue before determining the site to be down. The Ping Server is designed to send automated email messages whenever a site is determined to be down. The user can designate one or more email recipients to send the messages to, allowing users to send to inboxes, text messaging pagers and/or cell phones simultaneously.