diff --git a/Gemfile b/Gemfile
index fa75df1..426de69 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,3 +1,6 @@
 source 'https://rubygems.org'
-
 gemspec
+
+gem 'pry'
+gem 'pry-nav'
+gem 'pry-stack_explorer'
diff --git a/app/jobs/cangaroo/job.rb b/app/jobs/cangaroo/job.rb
index d1bf58a..119f900 100644
--- a/app/jobs/cangaroo/job.rb
+++ b/app/jobs/cangaroo/job.rb
@@ -1,5 +1,6 @@
 module Cangaroo
   class Job < ActiveJob::Base
+    include Cangaroo::Log
     include Cangaroo::ClassConfiguration
 
     queue_as :cangaroo
@@ -10,6 +11,8 @@ class Job < ActiveJob::Base
     class_configuration :process_response, true
 
     def perform(*)
+      log.set_context(job: self)
+
       restart_flow(connection_request)
     end
 
@@ -21,11 +24,32 @@ def transform
       { type.singularize => payload }
     end
 
-    protected
+    def payload_state
+      other_translation = translation.related_translations.first
+
+      if other_translation.present?
+        :updated
+      else
+        :new
+      end
+    end
+
+    protected if !Rails.env.test?
 
     def connection_request
-      Cangaroo::Webhook::Client.new(destination_connection, path)
-        .post(transform, @job_id, parameters)
+      translation.save!
+
+      log.info 'attempting translation',
+        destination_connection: destination_connection.name,
+        path: path,
+        translation: translation
+
+      response = Cangaroo::Webhook::Client.new(destination_connection, path)
+        .post(transform, @job_id, parameters, translation)
+
+      translation.update_column :response, (response.blank?) ? {} : response
+
+      response
     end
 
     def restart_flow(response)
@@ -36,6 +60,11 @@ def restart_flow(response)
         return
       end
 
+      if response.blank?
+        log.info 'blank response; not processing'
+        return
+      end
+
       PerformFlow.call(
         source_connection: destination_connection,
         json_body: response.to_json,
@@ -58,5 +87,23 @@ def payload
     def destination_connection
       @connection ||= Cangaroo::Connection.find_by!(name: connection)
     end
+
+    def translation
+      # NOTE @job_id will remain consistent across retries
+      # TODO we should move this logic to the translation model
+
+      @translation ||= Cangaroo::Translation.where(job_id: @job_id).first_or_initialize(
+        # TODO use job in place of destination connection
+        # TODO use source job is place of source connection
+        #      ^ this will provide more detail to the user
+
+        source_connection: source_connection,
+        destination_connection: destination_connection,
+
+        object_type: self.type,
+
+        request: self.payload
+      )
+    end
   end
 end
diff --git a/app/models/cangaroo/attempt.rb b/app/models/cangaroo/attempt.rb
new file mode 100644
index 0000000..a2f6be9
--- /dev/null
+++ b/app/models/cangaroo/attempt.rb
@@ -0,0 +1,3 @@
+class Cangaroo::Attempt < ActiveRecord::Base
+  belongs_to :translation
+end
diff --git a/app/models/cangaroo/translation.rb b/app/models/cangaroo/translation.rb
new file mode 100644
index 0000000..224180c
--- /dev/null
+++ b/app/models/cangaroo/translation.rb
@@ -0,0 +1,63 @@
+module Cangaroo
+  class Translation < ActiveRecord::Base
+    include Cangaroo::Log
+
+    belongs_to :destination_connection, class_name: 'Cangaroo::Connection'
+    belongs_to :source_connection, class_name: 'Cangaroo::Connection'
+
+    has_many :attempts
+
+    def request=(payload)
+      super
+
+      self.object_id = nil
+      self.object_key = nil
+
+      determine_payload_identifier
+
+      self.request
+    end
+
+    def successful?
+      !!self.response
+    end
+
+    def related_translations
+      Cangaroo::Translation.where(
+        object_type: self.object_type,
+        object_key: self.object_key,
+        object_id: self.object_id,
+      )
+      .where.not(job_id: self.job_id)
+    end
+
+    def determine_object_key_from_payload
+      Rails.configuration.cangaroo.payload_keys.each do |payload_key|
+        if self.request[payload_key].present?
+          return payload_key
+        end
+      end
+
+      nil
+    end
+
+    def determine_payload_identifier
+      self.object_key = determine_object_key_from_payload
+
+      if self.object_key
+        self.object_id = self.request[self.object_key]
+      else
+        log.info 'unable to find primary key', translation: self
+      end
+    end
+
+    def retry
+      Cangaroo::PerformJobs.call(
+        # TODO this should be abstracted away into a interator that accepts json payloads
+        json_body: { self.object_type => [ self.request ] }.to_json,
+        source_connection: self.source_connection,
+        jobs: Rails.configuration.cangaroo.jobs
+      )
+    end
+  end
+end
diff --git a/cangaroo.gemspec b/cangaroo.gemspec
index 66eb502..69b8aa6 100644
--- a/cangaroo.gemspec
+++ b/cangaroo.gemspec
@@ -36,6 +36,7 @@ Gem::Specification.new do |s|
   s.add_development_dependency 'rubocop'
   s.add_development_dependency 'shoulda-matchers'
   s.add_development_dependency 'simplecov'
-  s.add_development_dependency 'sqlite3'
+  s.add_development_dependency 'pg'
   s.add_development_dependency 'webmock'
+  s.add_development_dependency 'faker'
 end
diff --git a/db/migrate/20160405214735_create_translations.rb b/db/migrate/20160405214735_create_translations.rb
new file mode 100644
index 0000000..33c8967
--- /dev/null
+++ b/db/migrate/20160405214735_create_translations.rb
@@ -0,0 +1,22 @@
+class CreateTranslations < ActiveRecord::Migration
+  def change
+    create_table :cangaroo_translations do |t|
+      t.references :source_connection, index: true
+      t.references :destination_connection, index: true
+
+      t.string :job_id
+
+      t.string :object_type
+      t.string :object_id
+      t.string :object_key
+
+      t.jsonb :request
+      t.jsonb :response
+
+      t.timestamps null: false
+    end
+
+    add_foreign_key :cangaroo_translations, :cangaroo_connections, column: :source_connection_id
+    add_foreign_key :cangaroo_translations, :cangaroo_connections, column: :destination_connection_id
+  end
+end
diff --git a/db/migrate/20160406003211_create_cangaroo_attempts.rb b/db/migrate/20160406003211_create_cangaroo_attempts.rb
new file mode 100644
index 0000000..418aa99
--- /dev/null
+++ b/db/migrate/20160406003211_create_cangaroo_attempts.rb
@@ -0,0 +1,13 @@
+class CreateCangarooAttempts < ActiveRecord::Migration
+  def change
+    create_table :cangaroo_attempts do |t|
+      t.references :translation, index: true
+      t.integer :response_code
+      t.jsonb :response
+
+      t.timestamps null: false
+    end
+
+    add_foreign_key :cangaroo_attempts, :cangaroo_translations, column: :translation_id
+  end
+end
diff --git a/lib/cangaroo/engine.rb b/lib/cangaroo/engine.rb
index 82da8dd..79fda7f 100644
--- a/lib/cangaroo/engine.rb
+++ b/lib/cangaroo/engine.rb
@@ -13,7 +13,9 @@ class Engine < ::Rails::Engine
       Rails.configuration.cangaroo = ActiveSupport::OrderedOptions.new
       Rails.configuration.cangaroo.jobs = []
       Rails.configuration.cangaroo.poll_jobs = []
+      Rails.configuration.cangaroo.process_response = true
       Rails.configuration.cangaroo.basic_auth = false
+      Rails.configuration.cangaroo.payload_keys = ['id']
     end
   end
 end
diff --git a/lib/cangaroo/webhook/client.rb b/lib/cangaroo/webhook/client.rb
index be03d3b..2fb74cc 100644
--- a/lib/cangaroo/webhook/client.rb
+++ b/lib/cangaroo/webhook/client.rb
@@ -12,7 +12,7 @@ def initialize(connection, path)
         @path = path
       end
 
-      def post(payload, request_id, parameters)
+      def post(payload, request_id, parameters, translation = nil)
         request_body = body(payload, request_id, parameters).to_json
 
         request_options = {
@@ -33,6 +33,14 @@ def post(payload, request_id, parameters)
 
         sanitized_response = sanitize_response(req)
 
+        if translation.present?
+          Cangaroo::Attempt.create!(
+            translation: translation,
+            response_code: req.response.code,
+            response: sanitized_response
+          )
+        end
+
         if %w(200 201 202 204).include?(req.response.code)
           sanitized_response
         else
diff --git a/spec/factories/cangaroo_connections.rb b/spec/factories/cangaroo_connections.rb
index 2b40786..b632840 100644
--- a/spec/factories/cangaroo_connections.rb
+++ b/spec/factories/cangaroo_connections.rb
@@ -3,7 +3,7 @@
     name :store
     url 'www.store.com'
     parameters { { first: 'first', second: 'second' } }
-    key '1e4e888ac66f8dd41e00c5a7ac36a32a9950d271'
-    token '8d49cddb4291562808bfca1bee8a9f7cf947a987'
+    key { SecureRandom.hex(13) }
+    token { SecureRandom.hex(13) }
   end
 end
diff --git a/spec/factories/translation_factory.rb b/spec/factories/translation_factory.rb
new file mode 100644
index 0000000..fa90a37
--- /dev/null
+++ b/spec/factories/translation_factory.rb
@@ -0,0 +1,17 @@
+FactoryGirl.define do
+  factory :translation, class: 'Cangaroo::Translation' do
+    source_connection { FactoryGirl.create(:cangaroo_connection, name: Faker::Company.name, url: Faker::Internet.domain_name) }
+    destination_connection { FactoryGirl.create(:cangaroo_connection, name: Faker::Company.name, url: Faker::Internet.domain_name) }
+
+    job_id { SecureRandom.uuid }
+    object_type 'customers'
+
+    request {
+      {
+        "id" => SecureRandom.random_number(1000),
+        "updated_at" => DateTime.now.iso8601,
+        "created_at" => DateTime.now.iso8601
+      }
+    }
+  end
+end
diff --git a/spec/interactors/cangaroo/perform_jobs_spec.rb b/spec/interactors/cangaroo/perform_jobs_spec.rb
index f4c7e43..b8ee467 100644
--- a/spec/interactors/cangaroo/perform_jobs_spec.rb
+++ b/spec/interactors/cangaroo/perform_jobs_spec.rb
@@ -18,8 +18,8 @@ class JobB < Cangaroo::Job; end
   end
 
   describe '.call' do
-    let(:job_a) { double('job_a', perform?: true, enqueue: nil) }
-    let(:job_b) { double('job_b', perform?: false, enqueue: nil) }
+    let(:job_a) { double('job_a', perform?: true, enqueue: nil, payload_state: :new) }
+    let(:job_b) { double('job_b', perform?: false, enqueue: nil, payload_state: :new) }
 
     context 'payload with objects' do
       let(:json_body) { load_fixture('json_payload_ok.json') }
diff --git a/spec/jobs/cangaroo/job_spec.rb b/spec/jobs/cangaroo/job_spec.rb
index 991bfdf..95a42e7 100644
--- a/spec/jobs/cangaroo/job_spec.rb
+++ b/spec/jobs/cangaroo/job_spec.rb
@@ -11,7 +11,7 @@ class FakeJob < Cangaroo::Job
     let(:job_class) { FakeJob }
     let(:destination_connection) { create(:cangaroo_connection) }
     let(:type) { 'orders' }
-    let(:payload) { { id: 'O123' } }
+    let(:payload) { { "id" => 'O123' } }
     let(:connection_response) { parse_fixture('json_payload_connection_response.json') }
 
     let(:options) do
@@ -43,11 +43,12 @@ class FakeJob < Cangaroo::Job
       it 'calls post on client' do
         job.perform
         expect(client).to have_received(:post)
-          .with(job.transform, job.job_id, email: 'info@nebulab.it')
+          .with(job.transform, job.job_id, { email: 'info@nebulab.it' }, an_instance_of(Cangaroo::Translation))
       end
 
       it 'restart the flow' do
         job.perform
+
         expect(Cangaroo::PerformFlow).to have_received(:call)
           .once
           .with(source_connection: destination_connection,
@@ -63,6 +64,31 @@ class FakeJob < Cangaroo::Job
         expect(Cangaroo::PerformFlow).to_not have_received(:call)
       end
 
+      it 'creates a translation record and stores the response' do
+        job.perform
+
+        translation = Cangaroo::Translation.find_by(job_id: job.job_id)
+
+        expect(translation).to_not be_nil
+        expect(translation.successful?).to eq(true)
+        expect(translation.destination_connection).to eq(destination_connection)
+        expect(translation.object_type).to eq('orders')
+        expect(translation.object_key).to eq('id')
+        expect(translation.object_id).to eq('O123')
+      end
+
+      context 'endpoint communication fails' do
+        it 'creates a unsuccessful translation model' do
+          client.stub(:post).and_raise('an error')
+
+          expect { job.perform }.to raise_error
+
+          translation = Cangaroo::Translation.find_by(job_id: job.job_id)
+          expect(translation).to_not be_nil
+          expect(translation.successful?).to eq(false)
+        end
+      end
+
       context 'endpoint provides a empty response' do
         it 'should not restart the flow' do
           allow(client).to receive(:post).and_return('')
@@ -81,5 +107,17 @@ class FakeJob < Cangaroo::Job
     describe '#transform' do
       it { expect(job_class.new(options).transform).to eq('order' => payload) }
     end
+
+    describe '#payload_state' do
+      let(:job) { job_class.new(options) }
+
+      it { expect(job.payload_state).to eq(:new) }
+
+      it 'returns updated when a previous matching payload exists' do
+        allow_any_instance_of(Cangaroo::Translation).to receive(:related_translations).and_return([OpenStruct.new()])
+
+        expect(job.payload_state).to eq(:updated)
+      end
+    end
   end
 end
diff --git a/spec/models/cangaroo/translation_spec.rb b/spec/models/cangaroo/translation_spec.rb
new file mode 100644
index 0000000..7c76618
--- /dev/null
+++ b/spec/models/cangaroo/translation_spec.rb
@@ -0,0 +1,51 @@
+require 'rails_helper'
+
+RSpec.describe Cangaroo::Translation, type: :model do
+  let(:translation) { FactoryGirl.build(:translation) }
+
+  before do
+    Rails.configuration.cangaroo.payload_keys = ['id', 'order_id']
+  end
+
+  describe '#related_translations' do
+    it 'returns other translation of this same object that have been sent through the pipeline' do
+      translation.save!
+
+      previous_translation = FactoryGirl.build(:translation)
+
+      previous_translation.object_type = translation.object_type
+      # copying the request will also copy the ID + key type on save
+      previous_translation.request = translation.request.deep_dup
+      previous_translation.request['another_field'] = Faker::Lorem.word
+      previous_translation.save!
+
+      expect(translation.related_translations).to_not be_empty
+      expect(translation.related_translations.first.id).to eq(previous_translation.id)
+    end
+
+    it 'returns an empty collection when on previous objects exist' do
+      expect(translation.related_translations).to be_empty
+    end
+  end
+
+  describe "#object_key" do
+    it "chooses the first primary key available" do
+      translation.request = {
+        "id" => nil,
+        "order_id" => 123
+      }
+
+      expect(translation.object_key).to eq("order_id")
+      expect(translation.object_id).to eq("123")
+    end
+
+    it 'returns nil when no key is available' do
+      translation.request = {
+        "order_id" => nil
+      }
+
+      expect(translation.object_key).to be_nil
+      expect(translation.object_id).to be_nil
+    end
+  end
+end
diff --git a/spec/rails_helper.rb b/spec/rails_helper.rb
index dc773c1..67bf980 100644
--- a/spec/rails_helper.rb
+++ b/spec/rails_helper.rb
@@ -1,6 +1,7 @@
 require 'simplecov'
 require 'codeclimate-test-reporter'
 require 'pry-byebug'
+require 'faker'
 
 SimpleCov.start 'rails' do
   add_group 'Commands', 'app/commands'
@@ -39,6 +40,7 @@
   # reset config before each spec
   config.before(:each) do
     Rails.configuration.cangaroo.basic_auth = false
+    Rails.configuration.cangaroo.process_response = true
     Rails.configuration.cangaroo.jobs = []
     Rails.configuration.cangaroo.poll_job = []
   end
diff --git a/spec/support/rails_app.rb b/spec/support/rails_app.rb
index d4e3be1..5139317 100644
--- a/spec/support/rails_app.rb
+++ b/spec/support/rails_app.rb
@@ -6,8 +6,7 @@
 
 require 'cangaroo'
 
-database_path = File.expand_path('../../../tmp/cangaroo_test.sqlite3', __FILE__)
-ENV['DATABASE_URL'] = "sqlite3://#{database_path}"
+ENV['DATABASE_URL'] = "postgres:///cangaroo_test"
 
 # Initialize our test app