Abstract: A software package is provided for monitoring data entered into a travel reservation booking software. Upon detection of a predetermined data entry sequence, the software package launches a routine to remind the agent to inquire as to whether the traveler wishes to purchase travel insurance. If travel insurance is desired, the software package provides an interface to a web server over the internet and pre-populates a data fields at the web server using previously monitored data. Once data entry is completed at the web server, the software package populates the booking software with data entered at the web server.