diff --git a/app/assets/javascripts/discourse/tests/acceptance/admin-watched-words-test.js b/app/assets/javascripts/discourse/tests/acceptance/admin-watched-words-test.js
index 532e79904b7..ae17562d630 100644
--- a/app/assets/javascripts/discourse/tests/acceptance/admin-watched-words-test.js
+++ b/app/assets/javascripts/discourse/tests/acceptance/admin-watched-words-test.js
@@ -138,6 +138,33 @@ acceptance("Admin - Watched Words", function (needs) {
   });
 });
 
+acceptance("Admin - Watched Words - Emoji Replacement", function (needs) {
+  needs.user();
+  needs.site({
+    watched_words_replace: {
+      "(?:\\W|^)(betis)(?=\\W|$)": {
+        replacement: ":poop:",
+        case_sensitive: false,
+      },
+    },
+  });
+
+  test("emoji renders successfully after replacement", async function (assert) {
+    await visit("/t/internationalization-localization/280");
+    await click("button.reply-to-post");
+    await fillIn(".d-editor-input", "betis betis betis");
+    const cooked = query(".d-editor-preview p");
+    const cookedChildren = Array.from(cooked.children);
+    const emojis = cookedChildren.filter((child) => child.nodeName === "IMG");
+    assert.strictEqual(emojis.length, 3, "three emojis have been rendered");
+    assert.strictEqual(
+      emojis.every((emoji) => emoji.title === ":poop:"),
+      true,
+      "all emojis are :poop:"
+    );
+  });
+});
+
 acceptance("Admin - Watched Words - Bad regular expressions", function (needs) {
   needs.user();
   needs.pretender((server, helper) => {
diff --git a/app/assets/javascripts/pretty-text/engines/discourse-markdown/emoji.js b/app/assets/javascripts/pretty-text/engines/discourse-markdown/emoji.js
index df735a5fd1c..ce7f619e94b 100644
--- a/app/assets/javascripts/pretty-text/engines/discourse-markdown/emoji.js
+++ b/app/assets/javascripts/pretty-text/engines/discourse-markdown/emoji.js
@@ -195,7 +195,8 @@ function applyEmoji(
   emojiUnicodeReplacer,
   enableShortcuts,
   inlineEmoji,
-  customEmojiTranslation
+  customEmojiTranslation,
+  watchedWordsReplacer
 ) {
   let result = null;
   let start = 0;
@@ -204,6 +205,25 @@ function applyEmoji(
     content = emojiUnicodeReplacer(content);
   }
 
+  if (watchedWordsReplacer) {
+    const watchedWordRegex = Object.keys(watchedWordsReplacer);
+
+    watchedWordRegex.forEach((watchedWord) => {
+      if (content?.match(watchedWord)) {
+        const regex = new RegExp(watchedWord, "g");
+        const matches = content.match(regex);
+        const replacement = watchedWordsReplacer[watchedWord].replacement;
+
+        matches.forEach(() => {
+          const matchingRegex = regex.exec(content);
+          if (matchingRegex) {
+            content = content.replace(matchingRegex[1], replacement);
+          }
+        });
+      }
+    });
+  }
+
   let end = content.length;
 
   for (let i = 0; i < content.length - 1; i++) {
@@ -337,7 +357,8 @@ export function setup(helper) {
           md.options.discourse.emojiUnicodeReplacer,
           md.options.discourse.features.emojiShortcuts,
           md.options.discourse.features.inlineEmoji,
-          md.options.discourse.customEmojiTranslation
+          md.options.discourse.customEmojiTranslation,
+          md.options.discourse.watchedWordsReplace
         )
       )
     );