diff --git a/spec/services/word_watcher_spec.rb b/spec/services/word_watcher_spec.rb
index 48ce215e43..5129253868 100644
--- a/spec/services/word_watcher_spec.rb
+++ b/spec/services/word_watcher_spec.rb
@@ -48,6 +48,18 @@ describe WordWatcher do
         expect(m[1]).to eq("acknowledge")
       end
 
+      context "word boundary" do
+        it "handles word boundary" do
+          Fabricate(:watched_word, word: "love", action: WatchedWord.actions[:require_approval])
+          expect(WordWatcher.new("I Love, bananas.").word_matches_for_action?(:require_approval)[1]).to eq("love")
+          expect(WordWatcher.new("I LOVE; apples.").word_matches_for_action?(:require_approval)[1]).to eq("love")
+          expect(WordWatcher.new("love: is a thing.").word_matches_for_action?(:require_approval)[1]).to eq("love")
+          expect(WordWatcher.new("I love. oranges").word_matches_for_action?(:require_approval)[1]).to eq("love")
+          expect(WordWatcher.new("I :love. pineapples").word_matches_for_action?(:require_approval)[1]).to eq("love")
+          expect(WordWatcher.new("peace ,love and understanding.").word_matches_for_action?(:require_approval)[1]).to eq("love")
+        end
+      end
+
       context "emojis" do
         it "handles emoji" do
           Fabricate(:watched_word, word: ":joy:", action: WatchedWord.actions[:require_approval])