This chapter studies the vicarious liability of the supervising attorney with respect to the digital mistakes committed by their trainees, further emphasizing the importance of the legal profession – where even minor errors can lead to a missed opportunity. The overseeing attorney undoubtedly bears heavy risks and should, therefore carefully monitor and guide the work of their trainees to correct any mistake, especially those that are of a digital nature, to prevent adverse outcomes. The study will establish the role and qualifications of the supervising attorney in which eligibility to train legal interns will be established. It will also elucidate the rights, responsibilities, and duties of the trainee within the le-gal training framework regarding their position. This chpater studies each form of vicarious liability that would be borne by a supervising attorney in the event of digital errors done by their trainees and classifies such liabilities under two heads: tortious and contractual. By thoroughly exploring these elements, the study attempts to provide detailed knowledge of the legal implications for both solicitors and trainees and to give an insight into proper allocation and management of responsibility in the context of legal training.