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Why Oscar Health (OSCR) Stock Is Trading Up Today

By: StockStory
October 21, 2025 at 11:16 AM EDT

OSCR Cover Image

What Happened?

Shares of health insurance company Oscar Health (NYSE: OSCR) jumped 3% in the morning session after the company announced it was expanding its health insurance coverage and introducing new AI-powered tools and specialized health plans for the 2026 open enrollment period. The company revealed its health plans would become available in 573 counties across 20 states, with new expansions into Alabama and Mississippi. To improve the customer experience, Oscar launched a personal AI agent named Oswell, powered by OpenAI, to provide members with on-demand support. The company also introduced several new offerings, including what it described as the first-ever menopause-focused plan in the individual market, called HelloMeno. The plan offered benefits such as $0 primary doctor visits and the potential for members to save up to $900 a year. A new digital rewards program, Oscar Unlocks, was also introduced to promote healthy actions.

After the initial pop the shares cooled down to $21.14, up 4.7% from previous close.

Is now the time to buy Oscar Health? Access our full analysis report here.

What Is The Market Telling Us

Oscar Health’s shares are extremely volatile and have had 67 moves greater than 5% over the last year. In that context, today’s move indicates the market considers this news meaningful but not something that would fundamentally change its perception of the business.

The previous big move we wrote about was 11 days ago when the stock dropped 6.5% as worries over worsening trade relations with China were triggered by critical comments from President Donald Trump. The president's tone and the suggestion of canceling a meeting with President Xi caused a rapid sell-off in the market. The trade dispute flared up after China imposed export controls on rare earth minerals, which are critical components for high-tech manufacturing. The escalation of the trade war raises concerns about supply chain disruptions and increased costs for technology companies, which are heavily reliant on global trade, leading to a broad sell-off in the sector.

Oscar Health is up 56% since the beginning of the year, and at $21.14 per share, it is trading close to its 52-week high of $22.47 from October 2025. Investors who bought $1,000 worth of Oscar Health’s shares at the IPO in March 2021 would now be looking at an investment worth $607.37.

Today’s young investors won’t have read the timeless lessons in Gorilla Game: Picking Winners In High Technology because it was written more than 20 years ago when Microsoft and Apple were first establishing their supremacy. But if we apply the same principles, then enterprise software stocks leveraging their own generative AI capabilities may well be the Gorillas of the future. So, in that spirit, we are excited to present our Special Free Report on a profitable, fast-growing enterprise software stock that is already riding the automation wave and looking to catch the generative AI next.

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