NEW YORK, October 21, 2026 – 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 applying their rules. Matter History, a record of who or what makes every change on a legal matter, builds deeper trust across teammates, workflows, AI agents, and integrations. Legal knows who owns what and can show the business where work is waiting.
Having launched an intake product in 2019 and its AI legal front door in 2023, Checkbox is at the forefront as the biggest names in legal AI arrive. Several providers recently launched legal front doors for in-house teams in rapid succession. AI agents capture, clarify and act on requests alongside lawyers, workflows and connected tools, but accountability hasn’t always kept pace with the AI. 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.
As agents take on more work, in-house teams need two things after intake: rules that decide what AI can do and see, and a record of who or what changed each matter and when. Checkbox’s AI works on requests inside workflows that legal builds and controls to determine where each request goes and who signs off. Matter History records the actions of Checkbox’s AI agent and deterministic workflows in the same place as the work done by people.
“Anyone can build a legal front door, but what matters is what happens behind it,” said Evan Wong, co-founder and CEO of Checkbox. “Legal always needs to know who did what, and especially now that AI agents are taking on more work, that its own rules decide the outcome. Putting every change on the record is the level of transparency that lets legal teams use more AI.”
Checkbox’s new product updates include:
- Matter History: A History tab on every matter 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.
- 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.
