diff --git a/test/error_lifecycle.rb b/test/error_lifecycle.rb
new file mode 100644
index 0000000..db89cd5
--- /dev/null
+++ b/test/error_lifecycle.rb
@@ -0,0 +1,49 @@
+class MyStandardError < StandardError; end
+class MyException< Exception; end
+
+class ErrorLifeCycleTester
+  attr_reader :inner_attempted, :inner_else, :inner_rescue, :inner_ensure, :inner_ensure_has_time_to_finish,
+              :outer_rescue, :outer_else, :outer_ensure, :outer_ensure_has_time_to_finish
+
+  def subject(error_to_raise, error_to_rescue)
+    @inner_attempted = false
+    @inner_else = false
+    @inner_rescue = false
+    @inner_ensure = false
+    @inner_ensure_has_time_to_finish = false
+
+    @outer_rescue = false
+    @outer_else = false
+    @outer_ensure = false
+    @outer_ensure_has_time_to_finish = false
+
+    begin
+      Timeout.timeout(0.001, error_to_raise) do
+        @inner_attempted = true
+        nil while true
+      rescue error_to_rescue
+        @inner_rescue = true
+      else
+        @inner_else = true
+      ensure
+        @inner_ensure = true
+        t = Time.now; nil while Time.now < t+1
+        @inner_ensure_has_time_to_finish = true
+      end
+    rescue Exception
+      @outer_rescue = true
+    else
+      @outer_else = true
+    ensure
+      @outer_ensure = true
+      t = Time.now; nil while Time.now < t+1
+      @outer_ensure_has_time_to_finish = true
+    end
+
+    # this is here to avoid cluttering the "UNDESIRED?" section of each test,
+    # can be flatted into the main tests
+    unless @outer_else ^ @outer_rescue
+      raise "something strange happened with the outer_rescue variables"
+    end
+  end
+end
diff --git a/test/test_error_lifecycle.rb b/test/test_error_lifecycle.rb
new file mode 100644
index 0000000..87aaa42
--- /dev/null
+++ b/test/test_error_lifecycle.rb
@@ -0,0 +1,93 @@
+require 'test/unit'
+require 'timeout'
+require 'thread'
+
+class TestErrorLifecycle < Test::Unit::TestCase
+
+  # Behavior marked "UNDESIRED?" is done so as John's opinion, these can/should be removed before the PR is merged
+
+  require_relative 'error_lifecycle.rb'
+
+  def core_assertions(s)
+    assert s.inner_attempted
+    assert !s.inner_else
+    assert s.inner_ensure
+    assert s.outer_ensure
+
+    # This can result in user's expectation of total possible time
+    # being very wrong
+    # t = Time.now; Timeout.timeout(0.1){begin; sleep 1; ensure; sleep 2; end} rescue puts Time.now-t
+    # => 2.106306
+    assert s.inner_ensure_has_time_to_finish
+    assert s.outer_ensure_has_time_to_finish
+  end
+
+  # when an exception to raise is not specified and the inner code does not catch Exception
+  def test_1
+    s = ErrorLifeCycleTester.new
+    s.subject(nil, StandardError)
+    core_assertions(s)
+
+    assert !s.inner_rescue
+    assert s.outer_rescue
+  end
+
+  # when an exception to raise is not specified and the inner code does catch Exception
+  def test_2
+    s = ErrorLifeCycleTester.new
+    s.subject(nil, Exception)
+    core_assertions(s)
+
+    assert s.inner_rescue # true in 1.9, false in gem 0.2.0, true in gem 0.4.0
+
+    # UNDESIRED?
+    assert !s.outer_rescue # false in 1.9 stdlib, true in gem 0.2.0, false in gem 0.4.0
+  end
+
+  # when an exception to raise is StandardError and the inner code does not catch Exception
+  def test_3
+    s = ErrorLifeCycleTester.new
+    s.subject(MyStandardError, StandardError)
+    core_assertions(s)
+
+    assert s.inner_rescue
+
+    # UNDESIRED?
+    assert !s.outer_rescue
+  end
+
+  # when an exception to raise is StandardError and the inner code does catch Exception
+  def test_4
+    s = ErrorLifeCycleTester.new
+    s.subject(MyStandardError, Exception)
+    core_assertions(s)
+
+    assert s.inner_rescue
+
+    # UNDESIRED?
+    assert !s.outer_rescue
+  end
+
+  # when an exception to raise is Exception and the inner code does not catch Exception
+  def test_5
+    s = ErrorLifeCycleTester.new
+    s.subject(MyException, StandardError)
+    core_assertions(s)
+
+    assert !s.inner_rescue
+    assert s.outer_rescue
+  end
+
+  # when an exception to raise is Exception and the inner code does catch Exception
+  def test_6
+    s = ErrorLifeCycleTester.new
+    s.subject(MyException, Exception)
+    core_assertions(s)
+  
+    assert s.inner_rescue
+
+    # UNDESIRED?
+    assert !s.outer_rescue
+  end
+
+end