So I just rewrote this and threw it at the beginning of the test. Evidently this module injection isn't properly coded for the upgrade.
Winning Answer
class MyMassiveObjectTest < ActiveSupport::TestCase
def self.when_reminder_sent(n, &blk)
context "when reminder #{n} was sent" do
setup { subject.free_trial_notice_sent = n }
blk.bind(self).call
end
end
def self.when_payment_was_received(&blk)
context 'when payment has been received' do
setup { subject.last_payment_received_at = 1.day.ago }
blk.bind(self).call
end
end