Datadog Considers $4 Billion Acquisition of Upwind

Datadog is considering the acquisition of cloud security startup Upwind in a deal valued at $4 billion. If completed, the transaction would be the largest acquisition in Datadog's history and the second-largest pure-play cybersecurity deal of 2026.

The potential purchase aims to broaden Datadog's capabilities in attack path analysis, container security, dynamic application security testing, and AI and data security posture management. The two companies previously entered advanced acquisition talks in July 2025 for a deal valued at approximately $1 billion, but those negotiations failed to result in a sale.

Upwind is currently evaluating the Datadog offer against a competing $300 million cash infusion from Bessemer Venture Partners. That investment would value the startup at $3.8 billion. Upwind CEO Amiram Shachar has previously expressed ambitions to build a market-leading cloud-native application protection platform, stating that the company capable of building the best such platform in the market is a "$100 billion company."