diff --git a/middleware/index.js b/middleware/index.js
index 9eed341a14a3..60919f6bdb50 100644
--- a/middleware/index.js
+++ b/middleware/index.js
@@ -34,6 +34,7 @@ import helpToDocs from './redirects/help-to-docs.js'
 import languageCodeRedirects from './redirects/language-code-redirects.js'
 import handleRedirects from './redirects/handle-redirects.js'
 import findPage from './find-page.js'
+import spotContentFlaws from './spot-content-flaws.js'
 import blockRobots from './block-robots.js'
 import archivedEnterpriseVersionsAssets from './archived-enterprise-versions-assets.js'
 import events from './events.js'
@@ -173,6 +174,7 @@ export default function (app) {
 
   // *** Config and context for rendering ***
   app.use(asyncMiddleware(instrument(findPage, './find-page'))) // Must come before archived-enterprise-versions, breadcrumbs, featured-links, products, render-page
+  app.use(asyncMiddleware(instrument(spotContentFlaws, './spot-content-flaws'))) // Must come after findPage
   app.use(instrument(blockRobots, './block-robots'))
 
   // Check for a dropped connection before proceeding
diff --git a/middleware/spot-content-flaws.js b/middleware/spot-content-flaws.js
new file mode 100644
index 000000000000..d05ce4c1f6b8
--- /dev/null
+++ b/middleware/spot-content-flaws.js
@@ -0,0 +1,32 @@
+// This middleware, exclusively in 'development' tries to spot flaws in
+// the content you're actively viewing.
+// The hopeful assumption is that if you're actively viewing this
+// page on localhost, you're actively working on its content.
+
+import path from 'path'
+
+import kleur from 'kleur'
+
+export default async function spotContentFlaws(req, res, next) {
+  const { page } = req.context
+  if (process.env.NODE_ENV === 'development' && page) {
+    const trailingSlashRedirects = (page.redirect_from || []).filter(
+      (uri) => uri.endsWith('/') && uri.startsWith('/')
+    )
+    if (trailingSlashRedirects.length > 0) {
+      console.warn(
+        `The page ${kleur.bold(path.relative(process.cwd(), page.fullPath))} has ${
+          trailingSlashRedirects.length
+        } redirect_from entries that have a trailing slash\n  ${kleur.yellow(
+          trailingSlashRedirects.join('\n  ')
+        )}`
+      )
+      console.log(
+        "If you're actively working on this page, consider",
+        kleur.bold('deleting all trailing slashes in redirect_from.\n')
+      )
+    }
+  }
+
+  return next()
+}
diff --git a/package-lock.json b/package-lock.json
index 4c024ca009ca..2e8f3b9a759e 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -47,6 +47,7 @@
         "imurmurhash": "^0.1.4",
         "js-cookie": "^3.0.1",
         "js-yaml": "^4.1.0",
+        "kleur": "4.1.4",
         "liquidjs": "^9.22.1",
         "lodash": "^4.17.21",
         "lodash-es": "^4.17.21",
@@ -13371,10 +13372,9 @@
       }
     },
     "node_modules/kleur": {
-      "version": "3.0.3",
-      "resolved": "https://registry.npmjs.org/kleur/-/kleur-3.0.3.tgz",
-      "integrity": "sha512-eTIzlVOSUR+JxdDFepEYcBMtZ9Qqdef+rnzWdRZuMbOywu5tO2w2N7rqjoANZ5k9vywhL6Br1VRjUIgTQx4E8w==",
-      "devOptional": true,
+      "version": "4.1.4",
+      "resolved": "https://registry.npmjs.org/kleur/-/kleur-4.1.4.tgz",
+      "integrity": "sha512-8QADVssbrFjivHWQU7KkMgptGTl6WAcSdlbBPY4uNF+mWr6DGcKrvY2w4FQJoXch7+fKMjj0dRrL75vk3k23OA==",
       "engines": {
         "node": ">=6"
       }
@@ -17831,6 +17831,15 @@
         "node": ">= 6"
       }
     },
+    "node_modules/prompts/node_modules/kleur": {
+      "version": "3.0.3",
+      "resolved": "https://registry.npmjs.org/kleur/-/kleur-3.0.3.tgz",
+      "integrity": "sha512-eTIzlVOSUR+JxdDFepEYcBMtZ9Qqdef+rnzWdRZuMbOywu5tO2w2N7rqjoANZ5k9vywhL6Br1VRjUIgTQx4E8w==",
+      "devOptional": true,
+      "engines": {
+        "node": ">=6"
+      }
+    },
     "node_modules/prop-types": {
       "version": "15.7.2",
       "resolved": "https://registry.npmjs.org/prop-types/-/prop-types-15.7.2.tgz",
@@ -22247,14 +22256,6 @@
         "node": ">=8"
       }
     },
-    "node_modules/uvu/node_modules/kleur": {
-      "version": "4.1.4",
-      "resolved": "https://registry.npmjs.org/kleur/-/kleur-4.1.4.tgz",
-      "integrity": "sha512-8QADVssbrFjivHWQU7KkMgptGTl6WAcSdlbBPY4uNF+mWr6DGcKrvY2w4FQJoXch7+fKMjj0dRrL75vk3k23OA==",
-      "engines": {
-        "node": ">=6"
-      }
-    },
     "node_modules/v8-compile-cache": {
       "version": "2.3.0",
       "resolved": "https://registry.npmjs.org/v8-compile-cache/-/v8-compile-cache-2.3.0.tgz",
@@ -33493,10 +33494,9 @@
       "integrity": "sha512-dcS1ul+9tmeD95T+x28/ehLgd9mENa3LsvDTtzm3vyBEO7RPptvAD+t44WVXaUjTBRcrpFeFlC8WCruUR456hw=="
     },
     "kleur": {
-      "version": "3.0.3",
-      "resolved": "https://registry.npmjs.org/kleur/-/kleur-3.0.3.tgz",
-      "integrity": "sha512-eTIzlVOSUR+JxdDFepEYcBMtZ9Qqdef+rnzWdRZuMbOywu5tO2w2N7rqjoANZ5k9vywhL6Br1VRjUIgTQx4E8w==",
-      "devOptional": true
+      "version": "4.1.4",
+      "resolved": "https://registry.npmjs.org/kleur/-/kleur-4.1.4.tgz",
+      "integrity": "sha512-8QADVssbrFjivHWQU7KkMgptGTl6WAcSdlbBPY4uNF+mWr6DGcKrvY2w4FQJoXch7+fKMjj0dRrL75vk3k23OA=="
     },
     "language-subtag-registry": {
       "version": "0.3.21",
@@ -36869,6 +36869,14 @@
       "requires": {
         "kleur": "^3.0.3",
         "sisteransi": "^1.0.5"
+      },
+      "dependencies": {
+        "kleur": {
+          "version": "3.0.3",
+          "resolved": "https://registry.npmjs.org/kleur/-/kleur-3.0.3.tgz",
+          "integrity": "sha512-eTIzlVOSUR+JxdDFepEYcBMtZ9Qqdef+rnzWdRZuMbOywu5tO2w2N7rqjoANZ5k9vywhL6Br1VRjUIgTQx4E8w==",
+          "devOptional": true
+        }
       }
     },
     "prop-types": {
@@ -40276,13 +40284,6 @@
         "kleur": "^4.0.3",
         "sade": "^1.7.3",
         "totalist": "^2.0.0"
-      },
-      "dependencies": {
-        "kleur": {
-          "version": "4.1.4",
-          "resolved": "https://registry.npmjs.org/kleur/-/kleur-4.1.4.tgz",
-          "integrity": "sha512-8QADVssbrFjivHWQU7KkMgptGTl6WAcSdlbBPY4uNF+mWr6DGcKrvY2w4FQJoXch7+fKMjj0dRrL75vk3k23OA=="
-        }
       }
     },
     "v8-compile-cache": {
diff --git a/package.json b/package.json
index c9c70c070ef8..c1960a4dcfa7 100644
--- a/package.json
+++ b/package.json
@@ -49,6 +49,7 @@
     "imurmurhash": "^0.1.4",
     "js-cookie": "^3.0.1",
     "js-yaml": "^4.1.0",
+    "kleur": "4.1.4",
     "liquidjs": "^9.22.1",
     "lodash": "^4.17.21",
     "lodash-es": "^4.17.21",