diff --git a/lib/apartment/railtie.rb b/lib/apartment/railtie.rb
index 04af0c96..31097cf2 100644
--- a/lib/apartment/railtie.rb
+++ b/lib/apartment/railtie.rb
@@ -24,26 +24,34 @@ class Railtie < Rails::Railtie
       ActiveRecord::Migrator.migrations_paths = Rails.application.paths['db/migrate'].to_a
     end
 
-    #   Hook into ActionDispatch::Reloader to ensure Apartment is properly initialized
-    #   Note that this doens't entirely work as expected in Development, because this is called before classes are reloaded
-    #   See the middleware/console declarations below to help with this. Hope to fix that soon.
-    #
+    # Make sure Apartment is reconfigured when the code is reloaded
+
     config.to_prepare do
-      next if ARGV.any? { |arg| arg =~ /\Aassets:(?:precompile|clean)\z/ }
-      next if ARGV.any? { |arg| arg == 'webpacker:compile' }
+      ActiveRecord::Base.reinitialize_apartment
+    end
 
-      begin
-        Apartment.connection_class.connection_pool.with_connection do
-          Apartment::Tenant.init
-        end
-      rescue ::ActiveRecord::NoDatabaseError, PG::ConnectionBad
-        # Since `db:create` and other tasks invoke this block from Rails 5.2.0,
-        # we need to swallow the error to execute `db:create` properly.
-        Rails.logger.warn do
-          'Failed to initialize Apartment because a database connection could not be established.'
+    #
+    # Ensure that Apartment::Tenant.init is called when
+    # a new connection is requested.
+    #
+    module ApartmentInitializer
+      def connection
+        super.tap do
+          unless @apartment_already_initialized
+            # To avoid infinite loops in work init is doing,
+            # we need to set @apartment_already_initialized to true
+            # before init is called
+            @apartment_already_initialized = true
+            Apartment::Tenant.init
+          end
         end
       end
+
+      def reinitialize_apartment
+        @apartment_already_initialized = false
+      end
     end
+    ActiveRecord::Base.singleton_class.prepend ApartmentInitializer
 
     #
     #   Ensure rake tasks are loaded
diff --git a/spec/examples/generic_adapter_examples.rb b/spec/examples/generic_adapter_examples.rb
index bc0b1390..1a8b44d4 100644
--- a/spec/examples/generic_adapter_examples.rb
+++ b/spec/examples/generic_adapter_examples.rb
@@ -25,7 +25,7 @@
                                              .instance_variable_get(:@queue)
                                              .size
 
-        expect(num_available_connections).to eq(1)
+        expect(num_available_connections).to eq(0)
       end
     end
   end