Telepsychiatry is a cost-effective alternative to in-person psychiatric consultations. The COVID-19 pandemic brought about a sharp spike in the utilization of telepsychiatry due to ongoing restrictions on gatherings and traveling. In recognition of the importance of telemedicine in general, and telepsychiatry specifically, telemedicine practice guidelines and telepsychiatry operational guidelines have been released. Due to the rising trend in telemedicine, the Insurance Regulatory and Development Authority of India (IRDIA) incorporated teleconsultation health insurance coverage at a level on par with regular in-person consultations. In contrast, in the United States of America, private insurance coverage for telepsychiatry has been in vogue for some time. In this paper we draw comparisons between India and the United States on telepsychiatry and health insurance. We compare the evolving regulatory policies of these two countries in relation to existing insurances plans that are available, the challenges in implementation of new regulations and the possible ways to overcome the challenges to make telepsychiatry affordable to all.