diff --git a/app/assets/javascripts/pretty-text/censored-words.js.es6 b/app/assets/javascripts/pretty-text/censored-words.js.es6
index fc5254f58d..9eac5ad68d 100644
--- a/app/assets/javascripts/pretty-text/censored-words.js.es6
+++ b/app/assets/javascripts/pretty-text/censored-words.js.es6
@@ -36,13 +36,14 @@ export function censorFn(censoredWords, censoredPattern, replacementLetter, watc
 
           try {
             let m = censorRegexp.exec(text);
+            const fourCharReplacement = new Array(5).join(replacementLetter);
 
             while (m && m[0]) {
               if (m[0].length > original.length) { return original; } // regex is dangerous
-              const replacement = new Array(m[0].length+1).join(replacementLetter);
               if (watchedWordsRegularExpressions) {
-                text = text.replace(new RegExp(`(${escapeRegexp(m[0])})(?![^\\(]*\\))`, "ig"), replacement);
+                text = text.replace(censorRegexp, fourCharReplacement);
               } else {
+                const replacement = new Array(m[0].length+1).join(replacementLetter);
                 text = text.replace(new RegExp(`(\\b${escapeRegexp(m[0])}\\b)(?![^\\(]*\\))`, "ig"), replacement);
               }
               m = censorRegexp.exec(text);
diff --git a/test/javascripts/lib/pretty-text-test.js.es6 b/test/javascripts/lib/pretty-text-test.js.es6
index 0fd5bf8616..df81da1cfc 100644
--- a/test/javascripts/lib/pretty-text-test.js.es6
+++ b/test/javascripts/lib/pretty-text-test.js.es6
@@ -617,7 +617,18 @@ QUnit.test("censoring", assert => {
       },
       censoredWords: 'xyz*|plee+ase'
     },
-    "<p>Pleased to meet you, but ■■■■■■■■■ call me later, ■■■123</p>",
+    "<p>Pleased to meet you, but ■■■■ call me later, ■■■■123</p>",
+    "supports words as regular expressions");
+
+  assert.cookedOptions(
+    "Meet downtown in your town at the townhouse on Main St.",
+    { siteSettings: {
+        watched_words_regular_expressions: true,
+        censored_pattern: null
+      },
+      censoredWords: '\\btown\\b'
+    },
+    "<p>Meet downtown in your ■■■■ at the townhouse on Main St.</p>",
     "supports words as regular expressions");
 });