diff --git a/actionpack/CHANGELOG.md b/actionpack/CHANGELOG.md
index bdccfb9805170..ab38408868e9f 100644
--- a/actionpack/CHANGELOG.md
+++ b/actionpack/CHANGELOG.md
@@ -1,3 +1,12 @@
+*   Fix `Rails.application.reload_routes!` from clearing almost all routes.
+
+    When calling `Rails.application.reload_routes!` inside a middleware of
+    a Rake task, it was possible under certain conditions that all routes would be cleared.
+    If ran inside a middleware, this would result in getting a 404 on most page you visit.
+    This issue was only happening in development.
+
+    *Edouard Chin*
+
 *   Add resource name to the `ArgumentError` that's raised when invalid `:only` or `:except` options are given to `#resource` or `#resources`
 
     This makes it easier to locate the source of the problem, especially for routes drawn by gems.
diff --git a/railties/lib/rails/application.rb b/railties/lib/rails/application.rb
index 1396613d52310..b79b41e844459 100644
--- a/railties/lib/rails/application.rb
+++ b/railties/lib/rails/application.rb
@@ -156,7 +156,7 @@ def run_load_hooks! # :nodoc:
 
     # Reload application routes regardless if they changed or not.
     def reload_routes!
-      routes_reloader.reload!
+      routes_reloader.execute_unless_loaded || routes_reloader.reload!
     end
 
     def reload_routes_unless_loaded # :nodoc:
diff --git a/railties/test/application/rake_test.rb b/railties/test/application/rake_test.rb
index 75e33bd274ce6..cecc04955473f 100644
--- a/railties/test/application/rake_test.rb
+++ b/railties/test/application/rake_test.rb
@@ -185,6 +185,26 @@ def test_code_statistics
       assert_match(/Code LOC: \d+\s+Test LOC: \d+\s+ Code to Test Ratio: 1:\w+/, rails("stats"))
     end
 
+    def test_reload_routes
+      add_to_config <<-RUBY
+        rake_tasks do
+          task do_something: :environment do
+            Rails.application.reload_routes!
+            puts Rails.application.routes.named_routes.to_h.keys.join(" ")
+          end
+        end
+      RUBY
+
+      app_file "config/routes.rb", <<-RUBY
+        Rails.application.routes.draw do
+          get "foo", to: "foo#bar", as: :my_great_route
+        end
+      RUBY
+
+      output = Dir.chdir(app_path) { `bin/rails do_something` }
+      assert_includes(output.lines.first, "my_great_route")
+    end
+
     def test_loading_specific_fixtures
       rails "generate", "model", "user", "username:string", "password:string"
       rails "generate", "model", "product", "name:string"