Objective: This thesis aided the 113 Suicide Prevention (113), the national suicide prevention center for The Netherlands, by investigating technical solutions for the helpline, implementing an e-learning prototype housing six suicidal personas within a conversational agent model, and evaluating and analyzing an experiment on its effect, which entailed interactions with one, two, and three simultaneous chats. Methods: The thesis conducted a participant observation with a total of seven triage-psychologists, organized three focus groups including triage-psychologists, managers, and training personnel with nearly forty participants, and administered an evaluation with thirty participants that included six triage-psychologist and twenty-four counselors regarding a prototype to assist in the training of 113's triage-psychologists. Prototype: The system specification provided a prototype with six personas where triage-psychologists can practice against one or many chatbots, or conversational agents, in different situations that pertain to training for 113. The conversational agents design was based upon the Rose of Leary interpersonal stance and the Beliefs, Desires, and Intentions (BDI) design paradigm. The system focused on how a conversational agent must react to triage-psychologists' inputs with respect to the subtleties in interpersonal communication and negotiation as it pertains to the 113 suicide helpline. Results: Evaluation results indicate that triage-psychologists found the learning environment motivational and the events in the environment as socially realistic. With the additional number of chats, counselors experienced an increase in three measurable areas: 1.) mental effort; 2.) situational awareness demand; and 3.) situational awareness supply; even so, counselors were positive about all learning aspects regarding the new software environment. Conclusion: This work identified the natural language processing, the BDI reasoning model plus natural language generation, and the usability and quality of the prototype as three areas of focus for 113 as they continue to improve their management of the helpline, its training, and research on suicide.