Staying connected with family, friends, and colleagues is easy for most people who live with or close to others. For educators who need to communicate lessons and schedules with their students, or businesses who communicate with new and existing customers, staying connected can be hard, especially in times of crisis and isolation. Specifically, we wanted to make remote communication between educators and students easier. Communicating time-sensitive information and confirming that students received messages can be hard; scaling communication from tens to thousands of students can make the problem more complex, impacting educator and student productivity, time, and overall experience. To meet this challenge, We developed Callouts, a simple, consistent, and scalable solution for educators to communicate with students using Cloud calling and chatbot services (Amazon Connect and Amazon Lex). In crisis times, such as a quarantine, this solution helps educators use an automated bot that calls students to communicate important messages, such as schedule changes, general announcements, and attendance confirmation.