The purpose of this study is to describe an interactive web-based breastfeeding monitoring system (LACTOR), illustrate its components, explain the theoretical framework, and discuss its assessment as a model for an innovative breastfeeding support intervention. Based on the self-regulation model from Bandura Social Cognitive Theory, we have developed an interactive web-based breastfeeding monitoring system using a breastfeeding diary. The system has two main components: the Mothers' Portal, where mothers can enter their breastfeeding data and receive notifications, and the Lactation Consultants' Portal, where mothers' data can be monitored. The system is designed to send notifications to mothers in case of breastfeeding problems using triggers such as inability to latch, sleepy infant, jaundice, and maternal sore nipples. A prospective, descriptive, mixed methods study was conducted to examine the feasibility, usability, and acceptability of LACTOR among breastfeeding mothers. Eligible mothers were asked to enter their breastfeeding data into the system daily for 30 days and then submit an online system evaluation survey. Twenty-six mother/infant dyads completed the study. Feasibility of the system was established by the mothers' compliance in entering breastfeeding data. The system proved to be user-friendly. The mothers said that the monitoring was beneficial and gave them an opportunity to track their children's feeding patterns and detect any problems early. Mothers also appreciated the notifications and interventions received through the system. We concluded that the system is feasible and acceptable among breastfeeding mothers and a promising tool for maintaining communication between mothers and lactation consultants.