Palo Alto Networks CEO Nikesh Arora held acquisition talks with Okta and later explored a potential deal for Datadog before the company moved ahead with its CyberArk and Chronosphere purchases, according to a report by The Information on Wednesday.

Throughout the final months of 2024 and into early 2025, Arora met multiple times with Todd McKinnon, Okta’s chief executive, to discuss possible product integration between the two companies. The talks ultimately broke down after the parties could not agree on valuation.

At the start of 2024, Okta’s market value was about $13.5 billion. Since then, the company’s stock has risen roughly 30%, bringing its market capitalization to nearly $23 billion.

In spring 2025, Arora also contacted Datadog CEO Olivier Pomel to explore a possible acquisition. Datadog’s public market valuation at the time was above $40 billion. Pomel was not interested in pursuing the proposal, and Palo Alto Networks never made a formal offer.

Datadog’s valuation has since roughly doubled to more than $80 billion, making a future transaction appear increasingly unlikely.

The sequence of talks shows how Palo Alto Networks has been weighing software assets across identity, observability, and cybersecurity as it expands beyond its core security platform. After the talks with Okta and Datadog did not lead to deals, Palo Alto Networks shifted to other acquisitions. The company announced a $25 billion agreement to buy CyberArk in July 2025, followed by a $3.35 billion acquisition of Chronosphere in January 2026. Chronosphere provides log data and observability tools and competes directly with Datadog.

Together, the CyberArk and Chronosphere deals contributed $338 million to the $3 billion in quarterly revenue Palo Alto Networks reported in April.

On Wednesday, Palo Alto Networks shares fell 0.38% to close at $338.60. Datadog shares rose 2.95% after the report, while Okta shares declined 1.12%.

When asked for comment, a Palo Alto Networks spokesperson said the company does not respond to “rumors or speculation.” Representatives for Datadog and Okta also declined to comment.

Arora’s acquisition strategy appears to remain active. According to recent reports, he is now evaluating companies that could complement Chronosphere’s capabilities. Potential targets include Cribl, a data management platform company valued at $3.5 billion, and ClickHouse, a database technology company that raised funding at a $15 billion valuation in January 2026.

Arora is also reportedly looking at possible deals in artificial intelligence security, a category that has drawn more attention as enterprise customers look for tools that can keep pace with changing attack methods and real-time monitoring needs. Shares of Chronosphere, which trades under the CHRN ticker, fell 4.64% on Wednesday.