diff --git a/app/javascript/mastodon/selectors/index.js b/app/javascript/mastodon/selectors/index.js
index d0212c379..106198f74 100644
--- a/app/javascript/mastodon/selectors/index.js
+++ b/app/javascript/mastodon/selectors/index.js
@@ -47,7 +47,18 @@ export const regexFromFilters = filters => {
 
   return new RegExp(filters.map(filter => {
     let expr = escapeRegExp(filter.get('phrase'));
-    return filter.get('whole_word') ? `\\b${expr}\\b` : expr;
+
+    if (filter.get('whole_word')) {
+      if (/^[\w]/.test(expr)) {
+        expr = `\\b${expr}`;
+      }
+
+      if (/[\w]$/.test(expr)) {
+        expr = `${expr}\\b`;
+      }
+    }
+
+    return expr;
   }).join('|'), 'i');
 };
 
diff --git a/app/lib/feed_manager.rb b/app/lib/feed_manager.rb
index c247ab21d..14cba70dc 100644
--- a/app/lib/feed_manager.rb
+++ b/app/lib/feed_manager.rb
@@ -200,10 +200,11 @@ class FeedManager
     active_filters = Rails.cache.fetch("filters:#{receiver_id}") { CustomFilter.where(account_id: receiver_id).active_irreversible.to_a }.to_a
 
     active_filters.select! { |filter| filter.context.include?(context.to_s) && !filter.expired? }
+
     active_filters.map! do |filter|
       if filter.whole_word
         sb = filter.phrase =~ /\A[[:word:]]/ ? '\b' : ''
-        eb = filter.phrase =~ /[[:word:]]\Z/ ? '\b' : ''
+        eb = filter.phrase =~ /[[:word:]]\z/ ? '\b' : ''
 
         /(?mix:#{sb}#{Regexp.escape(filter.phrase)}#{eb})/
       else