diff --git a/lib/failbot.js b/lib/failbot.js
index 0189ff27a9df..46ed67babdac 100644
--- a/lib/failbot.js
+++ b/lib/failbot.js
@@ -33,9 +33,11 @@ async function retryingGot(url, args) {
   )
 }
 
-export async function report(error, metadata) {
+export function report(error, metadata) {
   // If there's no HAYSTACK_URL set, bail early
-  if (!process.env.HAYSTACK_URL) return
+  if (!process.env.HAYSTACK_URL) {
+    return
+  }
 
   const backends = [
     new HTTPBackend({
@@ -47,6 +49,7 @@ export async function report(error, metadata) {
     app: HAYSTACK_APP,
     backends,
   })
+
   return failbot.report(error, metadata)
 }
 
diff --git a/lib/handle-exceptions.js b/lib/handle-exceptions.js
index a6ce0adc57e7..dda3894c9a21 100644
--- a/lib/handle-exceptions.js
+++ b/lib/handle-exceptions.js
@@ -10,7 +10,7 @@ process.on('uncaughtException', async (err) => {
 
   console.error(err)
   try {
-    await FailBot.report(err)
+    FailBot.report(err)
   } catch (failBotError) {
     console.warn('Even sending the uncaughtException error to FailBot failed!')
     console.error(failBotError)
@@ -20,7 +20,7 @@ process.on('uncaughtException', async (err) => {
 process.on('unhandledRejection', async (err) => {
   console.error(err)
   try {
-    await FailBot.report(err)
+    FailBot.report(err)
   } catch (failBotError) {
     console.warn('Even sending the unhandledRejection error to FailBot failed!')
     console.error(failBotError)
diff --git a/middleware/render-page.js b/middleware/render-page.js
index 6f219eaf2408..8f4a1e054254 100644
--- a/middleware/render-page.js
+++ b/middleware/render-page.js
@@ -1,5 +1,6 @@
 import { get } from 'lodash-es'
 
+import FailBot from '../lib/failbot.js'
 import patterns from '../lib/patterns.js'
 import getMiniTocItems from '../lib/get-mini-toc-items.js'
 import Page from '../lib/page.js'
@@ -40,6 +41,13 @@ async function buildMiniTocItems(req) {
 
 export default async function renderPage(req, res, next) {
   const { context } = req
+
+  // This is a contextualizing the request so that when this `req` is
+  // ultimately passed into the `Error.getInitialProps` function,
+  // which NextJS executes at runtime on errors, so that we can
+  // from there send the error to Failbot.
+  req.FailBot = FailBot
+
   const { page } = context
   const path = req.pagePath || req.path
   browserCacheControl(res)
diff --git a/next.config.js b/next.config.js
index e427ea4c616b..bf3db7e25424 100644
--- a/next.config.js
+++ b/next.config.js
@@ -1,6 +1,8 @@
 import fs from 'fs'
-import frontmatter from 'gray-matter'
 import path from 'path'
+
+import frontmatter from 'gray-matter'
+
 const homepage = path.posix.join(process.cwd(), 'content/index.md')
 const { data } = frontmatter(fs.readFileSync(homepage, 'utf8'))
 const productIds = data.children
diff --git a/pages/500.tsx b/pages/500.tsx
deleted file mode 100644
index 0b75f32263f4..000000000000
--- a/pages/500.tsx
+++ /dev/null
@@ -1,5 +0,0 @@
-import { GenericError } from 'components/GenericError'
-
-export default function Custom500() {
-  return <GenericError />
-}
diff --git a/pages/_error.tsx b/pages/_error.tsx
index 2f6fd315f8b3..11ab2864836f 100644
--- a/pages/_error.tsx
+++ b/pages/_error.tsx
@@ -1,10 +1,104 @@
-import { NextPage } from 'next'
-import { GenericError } from 'components/GenericError'
+import type { NextPageContext } from 'next'
 
-type Props = {}
+import { GenericError } from 'components/GenericError'
 
-const ErrorPage: NextPage<Props> = () => {
+function Error() {
   return <GenericError />
 }
 
-export default ErrorPage
+Error.getInitialProps = async (ctx: NextPageContext) => {
+  // If this getInitialProps() is called in client-side rendering,
+  // you won't have a `.res` object. It's only present when it's
+  // rendered Node (SSR). That's our clue to know that, we should
+  // send this error to Failbot.
+  // In client-side, it's undefined. In server, it's a ServerResponse object.
+  const { err, req, res } = ctx
+  let statusCode = 500
+  if (res?.statusCode) {
+    statusCode = res.statusCode
+  }
+
+  // 'err' will by falsy if it's a 404
+  // But note, at the time of writing this comment, we have a dedicated
+  // `pages/404.tsx` which takes care of 404 messages.
+  if (err && res && req) {
+    // This is a (necessary) hack!
+    // You can't import `../lib/failbot.js` here in this
+    // file because it gets imported by webpack to be used in the
+    // client-side JS bundle. It *could* be solved by overriding
+    // the webpack configuration in our `next.config.js` but this is prone
+    // to be fragile since ignoring code can be hard to get right
+    // and the more we override there, the harder it will become to
+    // upgrade NextJS in the future because of moving parts.
+    // So the solution is to essentially do what the contextualizers
+    // do which mutate the Express request object by attaching
+    // callables to it. This way it's only ever present in SSR executed
+    // code and doesn't need any custom webpack configuration.
+    const expressRequest = req as any
+    const FailBot = expressRequest.FailBot
+    if (FailBot) {
+      try {
+        // An inclusion-list of headers we're OK with sending because
+        // they don't contain an PII.
+        const OK_HEADER_KEYS = ['user-agent', 'referer', 'accept-encoding', 'accept-language']
+        const reported = FailBot.report(err, {
+          path: req.url,
+          request: JSON.stringify(
+            {
+              method: expressRequest.method,
+              query: expressRequest.query,
+              language: expressRequest.language,
+            },
+            undefined,
+            2
+          ),
+          headers: JSON.stringify(
+            Object.fromEntries(
+              Object.entries(req.headers).filter(([k]) => OK_HEADER_KEYS.includes(k))
+            ),
+            undefined,
+            2
+          ),
+        })
+
+        // Within FailBot.report() (which is our wrapper for Failbot in
+        // the `@github/failbot` package), it might exit only because
+        // it has no configured backends to send to. I.e. it returns undefined.
+        // Otherwise, it should return `Array<Promise<Response | void>>`.
+        if (!reported) {
+          console.warn(
+            'The FailBot.report() returned undefined which means the error was NOT sent to Failbot.'
+          )
+        } else if (
+          Array.isArray(reported) &&
+          reported.length &&
+          reported.every((thing) => thing instanceof Promise)
+        ) {
+          // Make sure we await the promises even though we don't care
+          // about the results. This makes the code cleaner rather than
+          // letting the eventloop take care of it which could result
+          // in cryptic error messages if the await does fail for some
+          // reason.
+          try {
+            await Promise.all(reported)
+          } catch (error) {
+            console.warn('Unable to await reported FailBot errors', error)
+          }
+        }
+      } catch (error) {
+        // This does not necessarily mean FailBot failed to send. It's
+        // most likely that we failed to *send to* FailBot before it
+        // even has a chance to use the network. This is because
+        // `FailBot.report` returns an array of Promises which themselves
+        // could go wrong, but that's a story for another try/catch.
+        // Basically, this catch it just to avoid other errors that
+        // might prevent the pretty error page to render at all.
+        console.warn('Failed to send error to FailBot.', error)
+      }
+    }
+  }
+
+  return { statusCode, message: err?.message }
+}
+
+export default Error