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On September 3, SentinelOne (NYSE:S) expanded its Wayfinder Frontier AI Services with new tools built on OpenAI's latest cyber-focused model, arriving just a week after the company posted a quarter that beat every number management had guided to. Pairing a fresh AI product push with accelerating growth is the kind of combination that gets a cybersecurity stock noticed. The real question is whether the technology upgrade and the financial upgrade are actually pulling in the same direction, or whether one is masking strain in the other.
The Wayfinder expansion adds OpenAI's GPT-5.6-Cyber through the Daybreak Defense Network, OpenAI's cyber defense initiative that SentinelOne has participated in as a longtime member. The update brings two new capability areas, AI-Powered Code Risk Analysis and AI-Enabled Compromise Assessment, both built to scan for exploitable weaknesses and validate findings with SentinelOne's own security analysts rather than just handing customers a longer list. SentinelLABS, the company's research arm, benchmarked GPT-5.6-Cyber as best-in-class at reverse engineering and analyzing military-grade malware such as fast16. Chief Customer Officer Steve Stone framed the move around a widening gap, noting that attackers are already using AI to find and exploit weaknesses faster and at greater scale.
That AI push follows a second-quarter fiscal 2027 report, released August 27, that gave the bulls plenty to work with. Revenue grew 21% year over year to $292 million, ahead of guidance, and annualized recurring revenue climbed 22% to $1.218 billion. Customers spending $100,000 or more annually grew 13% to 1,715, and management raised its full-year revenue and operating income outlook. Profitability moved in the same direction: non-GAAP operating margin jumped to 10% from 2% a year earlier, and non-GAAP diluted earnings per share doubled to $0.08 from $0.04.
The GAAP picture complicates that story. Net loss actually widened to $93.4 million in the quarter, from $72.0 million a year earlier, even with revenue up sharply. Gross margin moved the wrong way too, with the GAAP figure slipping to 72% from 75% and the non-GAAP figure down to 77% from 79%. Restructuring charges jumped to $24.4 million in the quarter from just $3.9 million a year prior, a cost that ate directly into the bottom line. GAAP operating margin remained deeply negative at (31)%, a reminder that the non-GAAP profitability gains still sit on top of a business that is not yet profitable by standard accounting.
The new Wayfinder capabilities carry their own uncertainty. They are rolling out in private preview, with broader availability still to come, so there is no revenue tied to them yet. And the centerpiece of the announcement, GPT-5.6-Cyber, is a partner's model rather than SentinelOne's own technology, which means the company's frontier AI edge depends partly on how OpenAI continues to prioritize and support the Daybreak Defense Network.
Hedge fund ownership rose to 41 funds in the most recent quarter from 37 in the prior one, a sign of accumulating conviction rather than funds heading for the exits. Short interest sits at 5.41% of the float, high enough to reflect a genuine bear camp rather than routine hedging. The stock trades at a forward P/E of 73.53, as of September 16, a multiple that assumes a lot of future earnings growth actually shows up. Put together, more funds are buying in even as a meaningful group of short sellers bets against the stock, all while the market prices in aggressive growth.
SentinelOne is trying to prove that AI-native security tools can drive both faster growth and better margins at the same time, and the second quarter showed real progress on the non-GAAP side even as GAAP losses grew. The Wayfinder expansion adds a genuine technical hook, backed by SentinelLabs' own benchmarking, but it remains unproven revenue until the private preview graduates to broad release.
While we acknowledge the potential of S as an investment, we believe certain AI stocks offer greater upside potential and carry less downside risk. If you're looking for an extremely undervalued AI stock that also stands to benefit significantly from Trump-era tariffs and the onshoring trend, see our free report on the best short-term AI stock.
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