How Checkbox works

Four sources of evidence, one legal catalog, and a rules engine that turns what we observed into findings you can act on — with the citation, the states affected, the evidence and the fix.

1. Collect evidence from four sources

  • Synthetic shopper

    A headless Chromium browser visits your checkout as a shopper in each state you sell in (with that state’s timezone and location, and through regional proxies where configured), on desktop and mobile. In Stripe test mode it runs a synthetic test subscription end to end: it subscribes with a test card, receives your emails at a Checkbox inbox, fast-forwards through trial end and renewal with test clocks, and tries to cancel online.

  • JavaScript snippet

    A small script on your own pages records what real visitors see — including A/B variants the shopper may never get. When the content of a checkout changes, Checkbox re-scans it.

  • Billing platform

    The Stripe, Shopify and Recharge connectors read plan, trial, customer-portal and checkout settings, and turn subscription webhooks (trial ending, upcoming renewal, price change) into lifecycle events.

  • Email

    You BCC your transactional emails to a per-site capture address, and every synthetic sign-up gets its own inbox, so acknowledgment and reminder emails are captured and classified.

2. Check every stage of the lifecycle

Sign-up disclosures and consent

Before taking payment details, the automatic-renewal terms must be clear and conspicuous, next to the purchase button, and the customer must agree to them.

What is checked

  • Renews automatically until canceled
  • Recurring price and billing frequency
  • Cancellation policy and how to cancel
  • Free-trial length and the charge after it
  • Placement before the button, size and contrast
  • Affirmative consent; no pre-checked boxes

How

A headless browser loads your checkout as a shopper in each state (local timezone and location; regional IP addresses where configured) on desktop and mobile, measures where the terms sit relative to the button, and reads their size and contrast.

Acknowledgment email

After sign-up, the customer must receive an acknowledgment they can keep, restating the terms and explaining how to cancel (and, for trials, how to cancel before being charged).

What is checked

  • Sent promptly after sign-up
  • Restates the renewal terms
  • Explains how to cancel
  • Trial cancellation instructions

How

Each synthetic sign-up uses its own inbox, and you can BCC your transactional emails to a per-site address, so we read exactly what customers receive.

Trial, renewal and price-change reminders

Several states require a notice before a free trial converts, before long-term plans renew, at least once a year, or before a price goes up — each with its own window.

What is checked

  • Trial-ending reminder in the window
  • Annual-plan renewal reminder
  • Annual terms notice
  • Advance notice of price changes
  • Charge notices where required

How

Billing-platform webhooks tell us when a trial ends or a renewal is due; captured emails show whether the notice went out, and when.

Online cancellation

Customers who signed up online must be able to cancel online, without a phone call, a chat or an obstacle course of retention offers, and get a confirmation.

What is checked

  • Cancel online without calling
  • Cancel link easy to find
  • Limited save offers and steps
  • Cancellation confirmed

How

With a test account, the shopper logs in and tries to cancel, counting clicks and retention offers and recording every screen.

3. Evaluate against the law that applies

The legal catalog maps each requirement — federal and per state — to the machine checks that test it, with its citation, source, effective date and the conditions under which it applies (free trial, term length, payment method). Requirements with a future effective date switch on by themselves on that date.

Each check runs once and is reported once, with every state whose law requires it and the strictest severity among them. Checks are deterministic first — text patterns, page geometry, contrast — and an optional language model helps read disclosure text. Without enough evidence a check says needs review; it never guesses a pass.

See the laws and states covered →

Score and insurable status

Each site gets a score from 0 to 100, weighted by severity across the checks that apply to it. A site is insurable when it has no open critical or high-severity failures and no unverified critical checks. That flag is what the coming compliance warranty keys on.

4. Fix, and prove it

Every finding comes with platform-specific steps (Stripe Checkout, Shopify, Recharge or a custom checkout) and suggested copy filled in with your price and billing period. New, regressed and resolved findings are sent to email, Slack or a signed webhook.

Screenshots, page HTML, emails and platform settings go into a content-addressed, hash-chained evidence vault (write-once S3 Object Lock in production). You can verify the chain at any time and export a report for counsel.

What Checkbox is not

  • Not a law firm and not legal advice. The catalog is drafted from primary sources and pending attorney review.
  • Not a guarantee that a regulator or court will agree with an automated assessment.
  • Not a replacement for reviewing your terms of service and cancellation policy with counsel.

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