A monitoring station system and method for monitoring multiple dial-up points in a communications network, such as an Internet or intranet site. A single monitoring station runs dial monitor processes that can concurrently establish connections to, and test multiple dial-up points of, the site. Test data regarding availability and response time of the dial-up points can be obtained. Additionally, a transaction monitor process may run as a parent process of the dial monitor processes. The transaction monitor process provides service-specific monitors that use the established connections to the dial-up points to test services offered by, or via, the site, such as DHCP, HTTP and others. A different service of the site can be tested via each different connection. Specific testing is performed based on a profile that is tailored to customer needs. The connections may be established via analog modems, DSL modems, or ISDN terminal adapters/modems.