diff --git a/app/components/autocomplete_component.rb b/app/components/autocomplete_component.rb
index e7a75f665..d18b42864 100644
--- a/app/components/autocomplete_component.rb
+++ b/app/components/autocomplete_component.rb
@@ -56,7 +56,7 @@ class AutocompleteComponent < ApplicationComponent
   # highlight_matching_words("very_long_hair", "long_ha*") => "<span>very_</span><b>long</b><span>_</span><b>hair</b>"
   def highlight_matching_words(target, pattern)
     pattern_words = Tag.parse_query(pattern)
-    pattern_words.sort_by! { |word| [word.include?("*") ? 0 : 1, -word.size] }
+    pattern_words.sort_by! { |word| [word.include?("*") ? 1 : 0, -word.size] }
 
     target_words = Tag.split_words(target)
     target_words.map do |word|
diff --git a/test/functional/autocomplete_controller_test.rb b/test/functional/autocomplete_controller_test.rb
index 5acb481af..6c7a58cca 100644
--- a/test/functional/autocomplete_controller_test.rb
+++ b/test/functional/autocomplete_controller_test.rb
@@ -12,6 +12,17 @@ class AutocompleteControllerTest < ActionDispatch::IntegrationTest
     assert_equal(expected_value, autocomplete(query, type))
   end
 
+  def assert_autocomplete_highlights(expected_results, query, type = "tag_query")
+    get autocomplete_index_path(search: { query: query, type: type })
+    assert_response :success
+
+    results = response.parsed_body.css("li a").map do |html|
+      html.inner_html.strip.remove(/<\/?span>/).gsub(/<b>(.*?)<\/b>/) { $1.upcase }
+    end
+
+    assert_equal(results, expected_results)
+  end
+
   context "Autocomplete controller" do
     context "index action" do
       should "work for opensearch queries" do
@@ -34,6 +45,8 @@ class AutocompleteControllerTest < ActionDispatch::IntegrationTest
       end
 
       should "match tags containing the given words" do
+        create(:user, name: "foobar")
+        as(create(:user)) { create(:pool, name: "foobar") }
         create(:tag, name: "short_hair", post_count: 15_000)
         create(:tag, name: "long_hair", post_count: 10_000)
         create(:tag, name: "very_long_hair", post_count: 5_000)
@@ -42,32 +55,51 @@ class AutocompleteControllerTest < ActionDispatch::IntegrationTest
         create(:tag, name: "crying_with_eyes_open")
         create(:tag, name: "open_mouth")
         create(:tag, name: "black_hair")
+        create(:tag, name: "original")
         create(:tag_alias, antecedent_name: "dark_hair", consequent_name: "black_hair")
+        create(:tag_alias, antecedent_name: "oc", consequent_name: "original")
 
         assert_autocomplete_equals(%w[long_hair very_long_hair absurdly_long_hair], "long_hair")
         assert_autocomplete_equals(%w[souryuu_asuka_langley], "asuka")
         assert_autocomplete_equals(%w[crying_with_eyes_open], "open_eyes")
         assert_autocomplete_equals(%w[open_mouth], "mouth_open")
         assert_autocomplete_equals(%w[black_hair], "dark")
-      end
-
-      should "work for an aliased tag" do
-        create(:tag, name: "original")
-        create(:tag_alias, antecedent_name: "oc", consequent_name: "original")
-
-        assert_autocomplete_equals(["original"], "oc")
-      end
-
-      should "work for the user: metatag" do
-        create(:user, name: "foobar")
+        assert_autocomplete_equals(%w[original], "oc")
 
         assert_autocomplete_equals(["user:foobar"], "user:foo")
+        assert_autocomplete_equals(["pool:foobar"], "pool:foo")
       end
 
-      should "work for the pool: metatag" do
-        as(create(:user)) { create(:pool, name: "foobar") }
+      should "highlight matches correctly" do
+        create(:tag, name: "short_hair")
+        create(:tag, name: "very_long_hair")
+        create(:tag, name: "short_shorts")
+        create(:tag, name: "sleeves_rolled_up")
+        create(:tag, name: "jack-o'-lantern")
+        create(:tag, name: %q{don't_say_"lazy"})
 
-        assert_autocomplete_equals(["pool:foobar"], "pool:foo")
+        assert_autocomplete_highlights([%q{don't say "LAZY"}], "lazy")
+
+        assert_autocomplete_highlights(["VERY long hair"], "very")
+        assert_autocomplete_highlights(["very LONG hair"], "long")
+        assert_autocomplete_highlights(["short HAIR", "very long HAIR"], "hair")
+
+        assert_autocomplete_highlights(["SLEEVES ROLLED UP"], "sleeves_rolled_up")
+        assert_autocomplete_highlights(["SLEEVES ROLLED UP"], "rolled-up_sleeves")
+
+        assert_autocomplete_highlights(["JACK-O'-LANTERN"], "jack-o'-lantern")
+        assert_autocomplete_highlights(["JACK-O'-LANTERN"], "jack_o'_lantern")
+        assert_autocomplete_highlights(["JACK-O'-LANTERN"], "jack_o_lantern")
+
+        assert_autocomplete_highlights(["SHORT hair", "SHORT SHORTs"], "short")
+        assert_autocomplete_highlights(["SHORT SHOrts", "SHORT hair"], "short_sho")
+
+        assert_autocomplete_highlights(["VERY long hair"], "very*")
+        assert_autocomplete_highlights(["very LONG hair"], "*long*")
+        assert_autocomplete_highlights(["short HAIR", "very long HAIR"], "*hair")
+        assert_autocomplete_highlights(["VEry LOng HAir"], "*ve*lo*ha*")
+        assert_autocomplete_highlights(["vERy lONg hAIr"], "*er*on*ai*")
+        assert_autocomplete_highlights(["veRY loNG haIR"], "*ry*ng*ir*")
       end
 
       should "work for a missing type" do