Ride-hailing services will be legalized on August 22, 2027. The government has recently submitted a document to the Legislative Council outlining regulatory details for ride-hailing services. These include requirements such as drivers must be at least 21 years old, hold a Hong Kong Permanent Identity Card, possess a driving license for more than one year, have no serious traffic convictions within the past five years, and pass designated assessments and pre-service training courses. It is proposed that, in the initial phase, the number of ride-hailing vehicle licenses be capped at 10,000. In addition, applicant vehicles must be less than 12 years old, must carry third-party liability insurance covering ride-hailing use, and private cars must be registered under an individual’s name (i.e., “fixed driver–vehicle pairing”). These proposals have sparked widespread discussions across various sectors of society. As a stakeholder in Hong Kong’s motor insurance industry, we explore, from different angles, issues affecting private car owners considering entering the ride-hailing industry, including insurance terms, coverage, and premiums.