diff --git a/.markdownlint.json b/.markdownlint.json
index a476fe58fb98e0f..f8e478075dffb9f 100644
--- a/.markdownlint.json
+++ b/.markdownlint.json
@@ -102,5 +102,44 @@
     "style": "asterisk"
   },
   "MD051": false,
-  "MD052": false
+  "MD052": false,
+  "search-replace": {
+    "rules": [
+      {
+        "name": "curly-double-quotes",
+        "message": "Don't use curly double quotes",
+        "searchPattern": "/“|”/g",
+        "replace": "\"",
+        "skipCode": true
+      },
+      {
+        "name": "curly-single-quotes",
+        "message": "Don't use curly single quotes",
+        "searchPattern": "/‘|’/g",
+        "replace": "'",
+        "skipCode": true
+      },
+      {
+        "name": "m-dash",
+        "message": "Don't use '--'. Use m-dash — instead",
+        "search": " -- ",
+        "replace": " — ",
+        "skipCode": true
+      },
+      {
+        "name": "relative-link",
+        "message": "Internal links should start with '/'",
+        "search": "(en-US/docs",
+        "replace": "(/en-US/docs",
+        "skipCode": true
+      },
+      {
+        "name": "trailing-spaces",
+        "message": "Avoid trailing spaces",
+        "searchPattern": "/  +$/gm",
+        "replace": "",
+        "skipCode": false
+      }
+    ]
+  }
 }
diff --git a/package.json b/package.json
index 0a3e92ece585385..99b3de8a05a4e20 100644
--- a/package.json
+++ b/package.json
@@ -14,7 +14,7 @@
     "fix:md": "npm run lint:md -- --fix",
     "fix:yml": "prettier -w \"**/*.yml\"",
     "lint:json": "prettier -c \"**/*.json\"",
-    "lint:md": "markdownlint \"**/*.md\" -i node_modules",
+    "lint:md": "markdownlint \"**/*.md\" -i node_modules -r markdownlint-rule-search-replace",
     "lint:yml": "prettier -c \"**/*.yml\"",
     "start": "yarn up-to-date-check && env-cmd --silent cross-env CONTENT_ROOT=files REACT_APP_DISABLE_AUTH=true BUILD_OUT_ROOT=build yari-server",
     "up-to-date-check": "node scripts/up-to-date-check.js"
@@ -24,6 +24,7 @@
     "cross-env": "7.0.3",
     "env-cmd": "10.1.0",
     "markdownlint-cli": "0.32.2",
+    "markdownlint-rule-search-replace": "1.0.5",
     "prettier": "2.7.1"
   }
 }
diff --git a/yarn.lock b/yarn.lock
index 2fd27ac3db1273b..3894e08b4f7d61d 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -3070,6 +3070,13 @@ markdownlint-rule-helpers@~0.17.2:
   resolved "https://registry.yarnpkg.com/markdownlint-rule-helpers/-/markdownlint-rule-helpers-0.17.2.tgz#64d6e8c66e497e631b0e40cf1cef7ca622a0b654"
   integrity sha512-XaeoW2NYSlWxMCZM2B3H7YTG6nlaLfkEZWMBhr4hSPlq9MuY2sy83+Xr89jXOqZMZYjvi5nBCGoFh7hHoPKZmA==
 
+markdownlint-rule-search-replace@1.0.5:
+  version "1.0.5"
+  resolved "https://registry.yarnpkg.com/markdownlint-rule-search-replace/-/markdownlint-rule-search-replace-1.0.5.tgz#20cc1681e3c162dd43d19614e3d1515e75cf0299"
+  integrity sha512-PXpHZuZrqaPA0kpkPSsTPVndxtoM+wgG95V9vzL5sZl+SQUp8hJIHSqOnNJOwd85ykgjbnripZYf0IN40ADkdw==
+  dependencies:
+    markdownlint-rule-helpers "~0.17.2"
+
 markdownlint@~0.26.2:
   version "0.26.2"
   resolved "https://registry.yarnpkg.com/markdownlint/-/markdownlint-0.26.2.tgz#11d3d03e7f0dd3c2e239753ee8fd064a861d9237"