Introduction
Tesla's Full Self-Driving (FSD) technology recently attracted attention with a groundbreaking insurance offer from Shai Wininger, the co-founder and president of Lemonade. Wininger proposed a plan to insure Tesla vehicles utilizing the FSD feature for "almost free," a proposal that could significantly alter the landscape of vehicle insurance for Tesla owners.
Traditionally, insuring a Tesla has been perceived as a costly endeavor, attributable to the vehicles' advanced technology and expensive repair costs. However, the emergence of FSD technology has prompted tech entrepreneurs like Wininger to argue that these vehicles should be insured at lower rates, citing data that suggests Teslas operating on FSD are safer than those driven by humans.
The Promise of Full Self-Driving
The safety claims surrounding Tesla's FSD technology are bolstered by the company's own reports. In its Q2 2025 vehicle safety report, Tesla asserts that driving with FSD is nearly ten times safer than conventional driving. This assertion has sparked interest and debate among industry experts, consumers, and insurance providers.
Wininger, who heads Lemonade—an innovative insurance company boasting nearly two million customers—recently took to X to announce a new integration with Tesla vehicles. This integration is designed to enhance the insurance process for Tesla drivers, making it seamless and cost-effective.
Integration with Tesla Vehicles
According to Wininger, the direct integration with Tesla would eliminate the need for a usage-based insurance (UBI) device in their Pay Per Mile product. This innovation not only streamlines the activation process for Lemonade Car on Teslas but also reduces hardware and shipping costs, ultimately leading to lower insurance prices for Tesla drivers.
Wininger emphasized that the Tesla API provides richer and more accurate driving behavior data compared to traditional UBI devices, allowing for more precise risk assessment and pricing.
A Game-Changing Insurance Proposal
In his announcement, Wininger proposed a bold idea to Tesla's CEO, Elon Musk, suggesting that Lemonade would be "happy to explore insuring Tesla FSD miles for (almost) free." This proposition not only speaks to the potential for lower insurance costs but also incentivizes Tesla owners to make full use of the FSD suite.
Such an offer could transform the financial dynamics of owning a Tesla, making the experience more accessible and appealing for new buyers, especially in states where Tesla's in-house insurance is not available.
Lemonade’s Expansion Plans
Currently, Tesla Insurance is offered in twelve states, with plans to expand into Florida, although there have been no expansions in new states for the last three years. Wininger’s proposal could pave the way for Lemonade to fill the gap in states without Tesla's insurance, providing a much-needed alternative.
The potential of Lemonade insuring FSD miles for minimal costs presents an attractive prospect for Tesla owners looking to reduce their overall expenses. This innovative approach could broaden the appeal of Tesla vehicles, making them even more economical to own and operate.
The Broader Impact on the Insurance Industry
This development raises significant questions about how the traditional insurance industry may adapt in response to the evolving landscape of automotive technology. As FSD technology becomes more prevalent, insurance providers may need to reassess their models to remain competitive and relevant.
With the advent of safer driving technologies, the rationale for high insurance premiums could diminish, leading to a potential paradigm shift in how vehicle insurance is structured.
Conclusion
The proposal from Wininger to insure Tesla FSD miles for almost free stands as a testament to the changing dynamics within the automotive and insurance industries. As technology continues to advance, the way we approach vehicle insurance is likely to evolve, offering consumers new opportunities for savings and enhanced safety.
As this story develops, it will be essential to monitor how Tesla and Lemonade navigate this innovative insurance proposal and its implications for the broader market. The intersection of technology, safety, and affordability could redefine the future of vehicle ownership.