Telementoring is the remote guidance of a mentee by an expert mentor specialist through a procedure or surgery. Advances in technology and telecommunications have enabled live interactions connecting people across the world over the same surgical operating field. While galvanized by COVID-era restrictions on travel and increasing reliance on virtual interfaces, there are also many other drivers for interest in this modality. Rural, isolated, or underserved locations stand to gain from prompt access to specialists, and there is potential for this technology to be resource-efficient and cost-effective. This review describes some of the telementoring forays in the fields of endoscopy, laparoscopy, and robotic surgery. This is a rapidly evolving field as it is highly technology dependent. Some challenges lie ahead before it can enjoy broader adoption, but telementoring shows promise as an approach that can help address unmet needs in unique clinical settings.