diff --git a/lib/webhooks/README.md b/lib/webhooks/README.md
new file mode 100644
index 0000000000..07693be0d8
--- /dev/null
+++ b/lib/webhooks/README.md
@@ -0,0 +1,44 @@
+# Webhooks
+
+## About this directory
+
+* `lib/webhooks/index.js` is human-editable.
+* `lib/rest/static/**/*.payload.json` are manually edited and copied. When a new GHES release is created, the static webhook files from the previous version's directory are copied to a new version directory.
+
+## Editable files
+
+* `lib/webhooks/index.js` consumes the static JSON files in `lib/webhooks/static` and exports the data used by the REST middleware contextualizer.
+
+## Static files
+
+Generated by `script/rest/update-files.js`:
+
+* `lib/rest/static/dereferenced` - dereferenced OpenAPI schema file for each version of GitHub
+* `lib/rest/static/decorated` - files generated from the dereferenced OpenAPI schema with the Markdown descriptions rendered in HTML
+
+## Rendering docs
+
+When the server starts, `middleware/contextualizers/webhooks.js` accesses the data exported from the static webhook JSON files, fetches the data for the current version and requested path, and adds it to the `context` object. The added property is:
+
+* `req.context.webhookPayloadsForCurrentVersion` - all webhook payloads with a version matching the current version
+
+Markdown files in `content/developers/webhooks-and-events/webhooks/webhook-events-and-payloads.md` use Liquid to display the webhook payloads in `req.context.webhookPayloadsForCurrentVersion`. For example `{{ webhookPayloadsForCurrentVersion.user.created }}` references the payload file `user.created.payload.json` for the version being viewed.
+
+**Note** Payload files either contain the webhook action type or no action type at all. For example, `user.created.payload.json` is the webhook `user` with the action type of `created`. Not all webhooks have action types. If a file exists with no action type (e.g., `user.payload.json`) and the action types (e.g., `user.created.payload.json` and `user.deleted.payload.json`), the entry in the context for the file with no action type will be `default`. For example, for the three static file mentioned, the object would be:
+
+```
+{
+  user: {
+    default: "STRING VALUE",
+    created: "STRING VALUE",
+    deleted: "STRING VALUE"
+  }
+}
+```
+
+If no action types exist, and only `user.payload.json` exists, the object would be:
+
+```
+{
+  user: "STRING VALUE"
+}
diff --git a/lib/webhooks/index.js b/lib/webhooks/index.js
index f5a24bdc96..58f27065ac 100644
--- a/lib/webhooks/index.js
+++ b/lib/webhooks/index.js
@@ -19,7 +19,12 @@ versions.forEach((version) => {
   walk(versionSubdir, { includeBasePath: true }).forEach((payloadFile) => {
     // payload file: /path/to/check_run.completed.payload.json
     // payload path: check_run.completed
-    const payloadPath = path.basename(payloadFile).replace('.payload.json', '')
+    let payloadPath = path.basename(payloadFile).replace('.payload.json', '')
+    if (!payloadPath.includes('.') && payloadsPerVersion[payloadPath]) {
+      // append the key `default` to the payload path to
+      // prevent overwriting existing object
+      payloadPath = `${payloadPath}.default`
+    }
     set(
       payloadsPerVersion,
       payloadPath,
diff --git a/tests/rendering/webhooks.js b/tests/rendering/webhooks.js
new file mode 100644
index 0000000000..af6fff4a9e
--- /dev/null
+++ b/tests/rendering/webhooks.js
@@ -0,0 +1,32 @@
+import { jest } from '@jest/globals'
+import { getDOM } from '../helpers/supertest.js'
+import { allVersions } from '../../lib/all-versions.js'
+
+describe('webhooks events and payloads', () => {
+  jest.setTimeout(300 * 1000)
+
+  describe('rendering', () => {
+    test('every webhook event has at least one payload example', async () => {
+      const versions = Object.values(allVersions).map((value) => value.version)
+
+      // For all versions, check that the webhook events and payloads page
+      // has at least one payload example for each event. Payload examples
+      // start with the id `webhook-payload-example` and have a sibling div
+      // with the class `height-constrained-code-block`. The sibling is
+      // usually but not always the next sibling element, which is why
+      // `nextUntil` is used.
+      for (const version of versions) {
+        const page = `/${version}/developers/webhooks-and-events/webhooks/webhook-events-and-payloads`
+        const $ = await getDOM(page)
+        const payloadExampleElem = $('[id^=webhook-payload-example]')
+
+        payloadExampleElem.each((i, elem) => {
+          const siblings = $(elem)
+            .nextUntil('[id^=webhook-payload-example]')
+            .filter((i, elem) => $(elem).hasClass('height-constrained-code-block'))
+          expect(siblings.length).toBeGreaterThan(0)
+        })
+      }
+    })
+  })
+})