The article is devoted to the study of topical issues of legislative regulation of the concept of "transportation period" in Russian insurance law. The provisions of federal legislation regulating the start and end of the transportation period, as well as judicial practice, are analyzed. Controversial issues of legal regulation are identified. The specific features of the regulation of compensation for harm to the life and health of a passenger during transportation by off-road transport are considered. It is noted that due to the termination of the operation of monorail transport in Russia, the relevance of the legal regulation of carrier liability insurance has been lost. Specific proposals are being formulated to improve legislation aimed at increasing the level of legal certainty for participants in the transport process and insurers.