diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index a524e1b3e9d..8115ac0727e 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -46,17 +46,14 @@ module WebMock::API
   end
 end
 
+Dir[Rails.root.join("spec/support/**/*.rb")].each { |f| require f }
+
 # nuke the db (say, if `rake db:migrate RAILS_ENV=test` created records),
 # and then ensure people aren't creating records outside the rspec
 # lifecycle, e.g. inside a describe/context block rather than a
 # let/before/example
-require_relative 'support/blank_slate_protection'
 BlankSlateProtection.install!
 
-require_relative 'support/discourage_slow_specs'
-
-Dir[Rails.root.join("spec/support/**/*.rb")].each { |f| require f }
-
 ActionView::TestCase::TestController.view_paths = ApplicationController.view_paths
 
 # this makes sure that a broken transaction becomes functional again
diff --git a/spec/support/debuggable_timeout.rb b/spec/support/debuggable_timeout.rb
new file mode 100644
index 00000000000..f2e98f14dc8
--- /dev/null
+++ b/spec/support/debuggable_timeout.rb
@@ -0,0 +1,20 @@
+# disable timeouts (in particular the spec one) once we start a pry session
+#
+# note: there's not really a great way to detect when the session is done,
+# and making this only disable the spec timeout would be a lot more code.
+# so once you start up pry, all timeouts are disabled, but ¯\_(ツ)_/¯
+
+Timeout.singleton_class.prepend(Module.new {
+  def sleep(*)
+    result = super
+    in_debugger_land = defined?(Pry) && Pry::InputLock.input_locks.any?
+
+    if in_debugger_land
+      # abort the timeout thread, otherwise it will raise in the main
+      # thread once sleep returns
+      Thread.current.kill
+    end
+
+    result
+  end
+})