Checkbox, Legal's Front Door Since 2023, Puts Every AI Action on the Record

New Matter History records every change from intake to close, including those made by AI agents, to keep legal AI accountable

NEW YORK, Oct. 21, 2026 /PRNewswire/ -- Checkbox, the AI legal front door used by SAP, PepsiCo, and BILL, today launched new features that let in-house legal teams hand AI more work while maintaining command of the rules. Matter History is a record of every change on a legal matter and who or what made it, from a lawyer to an AI agent. Other new features include Tasks & Events for tracking deadlines on the matter, bulk editing across matters, and multi-document DocuSign envelopes.

Checkbox launched an intake product in 2019 and its AI legal front door in 2023, including contracts, conflicts of interest, privacy questions and employment matters. The biggest names in legal AI have since launched front doors for in-house teams in rapid succession. AI takes a first pass at the work, but accountability hasn't always kept pace. In a May 2026 survey of more than 1,000 U.S. corporate legal practitioners, only about 39% said they were confident they had real-time visibility into their AI agents' actions.

Checkbox's AI agent works on requests inside workflows that legal builds and controls, which determine where each request goes and who signs off. Matter History records the actions of the agent, deterministic workflows, and integrations in the same place as the work done by people, so legal can see who or what changed each matter and when.

"A legal front door should do more than take in requests. It should lead into a house where legal's rules decide the outcome," said Evan Wong, co-founder and CEO of Checkbox. "Legal always needs to know who did what, especially now that AI agents are taking on more work. Putting every change on the record is what lets legal teams use more AI without giving up control."

Checkbox's new product updates include:

• Matter History: A History tab on every matter, from contract reviews to conflict-of-interest disclosures, now lists changes newest first, including field updates with the before and after values, files, tasks and events, collaborators, and board moves. Each entry names who or what made the change, whether it's a person, a workflow, an AI agent, or an integration, giving legal an audit trail for every matter.
• Tasks & Events: Legal teams assign tasks with owners and due dates, add key dates such as an execution deadline, and see them in a calendar view inside the matter, so legal can see what's due and where work is waiting, instead of tracking them in spreadsheets and separate calendars.
• Board bulk editing: Status, assignee, requester, dates and most other matter fields can be edited directly on the board, and one change can apply across several matters at once.
• Multi-document DocuSign envelopes: A single signing step can send generated or uploaded documents together in one envelope, and each signed document returns to its own place on the matter.

Learn more at checkbox.ai.

About Checkbox

Checkbox is the AI front door that keeps in-house legal in command. Since 2019, Checkbox has helped legal structure how work enters, moves through, and gets resolved across the business. It captures requests from wherever the business already works, including Slack, Teams, email, Salesforce, Jira, and web forms. AI agents and no-code workflows handle the work under legal's own rules, from NDAs and DPAs to conflict of interest disclosures and contract approvals. More than 100 enterprise organizations use Checkbox, including SAP, PepsiCo, and BILL.

SOURCE Checkbox