diff --git a/app/models/message/searchable.rb b/app/models/message/searchable.rb
index 58ea47f..b792cd0 100644
--- a/app/models/message/searchable.rb
+++ b/app/models/message/searchable.rb
@@ -6,7 +6,15 @@ module Message::Searchable
     after_update_commit  :update_in_index
     after_destroy_commit :remove_from_index
 
-    scope :search, ->(query) { joins("join message_search_index idx on messages.id = idx.rowid").where("idx.body match ?", query).ordered }
+    scope :search, ->(query) { joins("join message_search_index idx on messages.id = idx.rowid").where("idx.body match ?", match_terms(query)).ordered }
+  end
+
+  class_methods do
+    # Quotes each word, so that FTS5 searches for AND, OR, NOT and NEAR rather than
+    # parsing them as operators, which fails on a query like "AND" or "salt AND".
+    def match_terms(query)
+      query.split.map { |word| %("#{word.gsub('"', '""')}") }.join(" ")
+    end
   end
 
   private
diff --git a/test/controllers/searches_controller_test.rb b/test/controllers/searches_controller_test.rb
index 80abfb4..34ff01b 100644
--- a/test/controllers/searches_controller_test.rb
+++ b/test/controllers/searches_controller_test.rb
@@ -20,6 +20,24 @@ class SearchesControllerTest < ActionDispatch::IntegrationTest
     assert_select ".message", text: /Hello world!/
   end
 
+  test "operator words are searched for as words" do
+    rooms(:designers).messages.create! body: "Salt and pepper", client_message_id: "operators", creator: users(:david)
+
+    get searches_url, params: { q: "salt AND" }
+
+    assert_response :success
+    assert_select ".message", text: /Salt and pepper/
+  end
+
+  test "searching for an operator word alone doesn't fail" do
+    %w[ AND OR NOT ].each do |word|
+      get searches_url, params: { q: word }
+
+      assert_response :success
+      assert_select ".message", count: 0
+    end
+  end
+
   test "unreachable messages are not found" do
     memberships(:david_designers).destroy!
 
diff --git a/test/models/message_test.rb b/test/models/message_test.rb
index 5ffecea..e6add9a 100644
--- a/test/models/message_test.rb
+++ b/test/models/message_test.rb
@@ -65,6 +65,12 @@ class MessageTest < ActiveSupport::TestCase
     assert_equal room.messages.ordered.first(Message::Pagination::PAGE_SIZE).map(&:id), room.messages.first_page.map(&:id)
   end
 
+  test "search reads quotes and operator words in the query as text" do
+    message = rooms(:designers).messages.create!(body: "Say hi, NOT bye", client_message_id: "quoted", creator: users(:david))
+
+    assert_equal [ message ], Message.search(%(say "hi NOT)).to_a
+  end
+
   private
     def create_new_message_in(room)
       room.messages.create!(creator: users(:jason), body: "Hello", client_message_id: "123")