Square Rolls Out Squaremates Agent to U.S. Merchants, Opens MCP and CLI

Payments company Square announced on 2026-11-12 that Squaremates, its merchant-facing AI agent, is now generally available (GA) in the United States and has become the primary entry point to Square Dashboard. Evolved from Managerbot, the tool runs in a separate, secure workspace and can execute multi-step tasks across the business—for example, identifying churning customers and generating targeted marketing campaigns, bulk-updating product catalogs, scheduling staff based on labor costs and sales trends, and producing chart-based sales reports and branded email content.

Square also launched an upgraded Square MCP and a brand-new Square CLI. According to its press release, Square MCP lets merchants connect their accounts to third-party AI assistants and authorize those tools to call Square's capabilities to perform actions; Square CLI opens command-line API access to developers for writing scripted workflows and building custom applications. Merchants can also use Squaremates Apps to build and host applications connected to their business, such as allocating cash tips by hours worked or monitoring schedules across locations.

Square is simultaneously extending agent capabilities beyond its own platform: a restocking feature in testing can identify low inventory and generate supplier orders pending merchant approval, and the company plans to add authorization-based email access for daily briefings. The move continues parent company Block's strategy of advancing AI on both the consumer and merchant sides; on the November earnings call, CEO Jack Dorsey mentioned a voice ordering terminal and plans for a procurement agent that manages inventory and places orders with suppliers.

For the agentic payments ecosystem, merchants authorizing third-party AI assistants to operate their accounts pushes the authorization-boundary question of "who is allowed to do what" down to the operational layer: MCP-style permission grants need to specify per-transaction limits, the scope of callable capabilities and an audit trail of actions before they can support subsequent money-related actions.

Source: https://www.pymnts.com/news/artificial-intelligence/2026/square-expands-agentic-ai-tools-give-sellers-more-control-over-business-operations/