diff --git a/app/assets/javascripts/discourse-common/addon/utils/watched-words.js b/app/assets/javascripts/discourse-common/addon/utils/watched-words.js
index 8ff622ce550..3641be2ad79 100644
--- a/app/assets/javascripts/discourse-common/addon/utils/watched-words.js
+++ b/app/assets/javascripts/discourse-common/addon/utils/watched-words.js
@@ -5,5 +5,5 @@ export function createWatchedWordRegExp(word) {
 
 export function toWatchedWord(regexp) {
   const [[regexpString, options]] = Object.entries(regexp);
-  return { regexp: regexpString, ...options };
+  return { ...options, regexp: regexpString };
 }
diff --git a/app/assets/javascripts/discourse-markdown-it/src/features/watched-words.js b/app/assets/javascripts/discourse-markdown-it/src/features/watched-words.js
index 5e0fc48a1b2..00f9d91fe1b 100644
--- a/app/assets/javascripts/discourse-markdown-it/src/features/watched-words.js
+++ b/app/assets/javascripts/discourse-markdown-it/src/features/watched-words.js
@@ -61,7 +61,7 @@ export function setup(helper) {
           const word = toWatchedWord({ [regexpString]: options });
 
           matchers.push({
-            word: new RegExp(options.word, options.case_sensitive ? "" : "i"),
+            word: new RegExp(options.regexp, options.case_sensitive ? "" : "i"),
             pattern: createWatchedWordRegExp(word),
             replacement: options.replacement,
             link: false,
@@ -76,7 +76,7 @@ export function setup(helper) {
           const word = toWatchedWord({ [regexpString]: options });
 
           matchers.push({
-            word: new RegExp(options.word, options.case_sensitive ? "" : "i"),
+            word: new RegExp(options.regexp, options.case_sensitive ? "" : "i"),
             pattern: createWatchedWordRegExp(word),
             replacement: options.replacement,
             link: true,
diff --git a/app/services/word_watcher.rb b/app/services/word_watcher.rb
index 442c7fca29c..4b5760de8a3 100644
--- a/app/services/word_watcher.rb
+++ b/app/services/word_watcher.rb
@@ -32,7 +32,12 @@ class WordWatcher
       .limit(WatchedWord::MAX_WORDS_PER_ACTION)
       .order(:id)
       .pluck(:word, :replacement, :case_sensitive)
-      .to_h { |w, r, c| [w, { word: w, replacement: r, case_sensitive: c }.compact] }
+      .to_h do |w, r, c|
+        [
+          word_to_regexp(w, match_word: false),
+          { word: w, replacement: r, case_sensitive: c }.compact,
+        ]
+      end
   end
 
   def self.words_for_action_exist?(action)
@@ -50,8 +55,8 @@ class WordWatcher
   end
 
   def self.regexps_for_action(action, engine: :ruby)
-    cached_words_for_action(action)&.to_h do |word, attrs|
-      [word_to_regexp(word, engine: engine), attrs]
+    cached_words_for_action(action)&.to_h do |_, attrs|
+      [word_to_regexp(attrs[:word], engine: engine), attrs]
     end
   end
 
diff --git a/lib/topic_creator.rb b/lib/topic_creator.rb
index 3a685b1d452..c184486de53 100644
--- a/lib/topic_creator.rb
+++ b/lib/topic_creator.rb
@@ -191,8 +191,8 @@ class TopicCreator
     if watched_words.present?
       word_watcher = WordWatcher.new("#{@opts[:title]} #{@opts[:raw]}")
       word_watcher_tags = topic.tags.map(&:name)
-      watched_words.each do |word, opts|
-        if word_watcher.word_matches?(word, case_sensitive: opts[:case_sensitive])
+      watched_words.each do |_, opts|
+        if word_watcher.word_matches?(opts[:word], case_sensitive: opts[:case_sensitive])
           word_watcher_tags += opts[:replacement].split(",")
         end
       end
diff --git a/spec/lib/pretty_text_spec.rb b/spec/lib/pretty_text_spec.rb
index 19def8b7df0..5997d439051 100644
--- a/spec/lib/pretty_text_spec.rb
+++ b/spec/lib/pretty_text_spec.rb
@@ -1981,6 +1981,19 @@ HTML
       HTML
     end
 
+    it "replaces words with wildcards" do
+      Fabricate(
+        :watched_word,
+        action: WatchedWord.actions[:replace],
+        word: "*dolor*",
+        replacement: "something else",
+      )
+
+      expect(PrettyText.cook("Lorem ipsum xdolorx sit amet")).to match_html(<<~HTML)
+        <p>Lorem ipsum something else sit amet</p>
+      HTML
+    end
+
     it "replaces words with links" do
       Fabricate(
         :watched_word,