diff --git a/app/jobs/update_bill_items.rb b/app/jobs/update_bill_items.rb
index 6867f64466..00dfd333db 100644
--- a/app/jobs/update_bill_items.rb
+++ b/app/jobs/update_bill_items.rb
@@ -5,11 +5,11 @@ UpdateBillItems = Struct.new(:lala) do
     start_date = (Time.now - 1.day).beginning_of_month
     end_date = Time.now.beginning_of_day
 
-    enterprises = Enterprise.select([:id, :name, :owner_id, :sells, :shop_trial_start_date])
+    enterprises = Enterprise.select([:id, :name, :owner_id, :sells, :shop_trial_start_date, :created_at])
 
-    # Cycle through users
+    # Cycle through enterprises
     enterprises.each do |enterprise|
-      # Cycle through owned_enterprises
+      # Cycle through previous versions of this enterprise
       versions = enterprise.versions.where('created_at >= (?)', start_date)
       bill_items = []
 
@@ -17,7 +17,7 @@ UpdateBillItems = Struct.new(:lala) do
       trial_expiry = enterprise.shop_trial_expiry
 
       versions.each do |version|
-        begins_at = bill_items.last.andand.ends_at || start_date
+        begins_at = bill_items.last.andand.ends_at || [start_date, enterprise.created_at].max
         ends_at = version.created_at
 
         split_for_trial(version.reify, begins_at, ends_at, trial_start, trial_expiry).each do |bill_item|
@@ -26,7 +26,7 @@ UpdateBillItems = Struct.new(:lala) do
       end
 
       # Update / create bill_item for current start
-      begins_at = bill_items.last.andand.ends_at || start_date
+      begins_at = bill_items.last.andand.ends_at || [start_date, enterprise.created_at].max
       ends_at = end_date
 
       split_for_trial(enterprise, begins_at, ends_at, trial_start, trial_expiry).each do |bill_item|
diff --git a/spec/jobs/update_bill_items_spec.rb b/spec/jobs/update_bill_items_spec.rb
index bc20108654..6d94999f22 100644
--- a/spec/jobs/update_bill_items_spec.rb
+++ b/spec/jobs/update_bill_items_spec.rb
@@ -5,18 +5,22 @@ describe UpdateBillItems do
     # Chose july to test with because June has 30 days and so is easy to calculate end date for shop trial
     let!(:start_of_july) { Time.now.beginning_of_year + 6.months }
 
+    let!(:enterprise) { create(:supplier_enterprise, sells: 'any') }
+
+    let!(:order1) { create(:order, completed_at: start_of_july + 5.days, distributor: enterprise) }
+    let!(:order2) { create(:order, completed_at: start_of_july + 15.days, distributor: enterprise) }
+    let!(:order3) { create(:order, completed_at: start_of_july + 25.days, distributor: enterprise) }
+
+    before do
+      order1.line_items = [ create(:line_item, price: 12.56, order: order1) ]
+      order2.line_items = [ create(:line_item, price: 87.44, order: order2) ]
+      order3.line_items = [ create(:line_item, price: 50.00, order: order3) ]
+      [order1, order2, order3].each(&:update!)
+    end
+
     context "where the enterprise existed at the beginning of the current billing period", versioning: true do
-      let!(:enterprise) { create(:supplier_enterprise, created_at: start_of_july - 2.months, sells: 'any') }
-
-      let!(:order1) { create(:order, completed_at: start_of_july + 5.days, distributor: enterprise) }
-      let!(:order2) { create(:order, completed_at: start_of_july + 15.days, distributor: enterprise) }
-      let!(:order3) { create(:order, completed_at: start_of_july + 25.days, distributor: enterprise) }
-
       before do
-        order1.line_items = [ create(:line_item, price: 12.56, order: order1) ]
-        order2.line_items = [ create(:line_item, price: 87.44, order: order2) ]
-        order3.line_items = [ create(:line_item, price: 50.00, order: order3) ]
-        [order1, order2, order3].each(&:update!)
+        enterprise.update_attribute(:created_at, start_of_july - 2.months)
       end
 
       context "where the sells property of the enterprise has not been altered within the current billing period" do
@@ -88,7 +92,7 @@ describe UpdateBillItems do
 
       context "where the sells property of the enterprise has been altered within the current billing period" do
         before do
-          Timecop.travel(start_of_july + 10.days) do
+          Timecop.freeze(start_of_july + 10.days) do
             # NOTE: Sells is changed between when order1 and order2 are placed
             enterprise.update_attribute(:sells, 'own')
           end
@@ -110,6 +114,7 @@ describe UpdateBillItems do
           it "splits the billing period into a separate item for each sells value" do
             expect(bill_items.count).to eq 2
             expect(bill_items.map(&:sells)).to eq ['any', 'own']
+            expect(bill_items.map(&:trial)).to eq [false, false]
           end
 
           it "splits the turnover for the month to date" do
@@ -121,10 +126,6 @@ describe UpdateBillItems do
         context "where a trial ended during the current billing period, after sells was changed" do
           before do
             enterprise.update_attribute(:shop_trial_start_date, start_of_july - 10.days)
-            Timecop.travel(start_of_july + 10.days) do
-              # NOTE: Sells is changed between when order1 and order2 are placed
-              enterprise.update_attribute(:sells, 'own')
-            end
             UpdateBillItems.new('lala').perform
           end
 
@@ -208,10 +209,212 @@ describe UpdateBillItems do
       end
     end
 
-    context "where the enterprise was created after the beginning of the current billing period" do
+    context "where the enterprise was created after the beginning of the current billing period", versioning: true do
+      before do
+        enterprise.update_attribute(:created_at, start_of_july + 7.days)
+      end
 
+      context "where the sells property of the enterprise has not been altered within the current billing period" do
+        before do
+          Timecop.travel(start_of_july + 28.days)
+        end
+
+        after do
+          Timecop.return
+        end
+
+        context "where no trial information has been set" do
+          before do
+            UpdateBillItems.new('lala').perform
+          end
+
+          let(:bill_items) { BillItem.order(:id) }
+
+          it "creates a single bill item" do
+            expect(bill_items.count).to eq 1
+            expect(bill_items.map(&:sells)).to eq ['any']
+            expect(bill_items.map(&:trial)).to eq [false]
+            expect(bill_items.map(&:begins_at)).to eq [start_of_july + 7.days]
+            expect(bill_items.map(&:ends_at)).to eq [start_of_july + 28.days]
+          end
+
+          it "ignores orders completed before the enterprise was created" do
+            expect(bill_items.first.turnover).to eq (order2.total + order3.total)
+          end
+        end
+
+        context "where a trial ended during the current billing period" do
+          before do
+            enterprise.update_attribute(:shop_trial_start_date, start_of_july - 10.days)
+            UpdateBillItems.new('lala').perform
+          end
+
+          let(:bill_items) { BillItem.order(:id) }
+
+          it "splits out the trial period into a separate bill item" do
+            expect(bill_items.count).to eq 2
+            expect(bill_items.map(&:sells)).to eq ['any', 'any']
+            expect(bill_items.map(&:trial)).to eq [true, false]
+            expect(bill_items.map(&:begins_at)).to eq [start_of_july + 7.days, start_of_july + 20.days]
+            expect(bill_items.map(&:ends_at)).to eq [start_of_july + 20.days, start_of_july + 28.days]
+          end
+
+          it "splits out the trial period into a separate bill item" do
+            expect(bill_items.first.turnover).to eq order2.total
+            expect(bill_items.last.turnover).to eq order3.total
+          end
+        end
+
+        context "where the trial began part-way through the current billing period" do
+          before do
+            enterprise.update_attribute(:shop_trial_start_date, start_of_july + 10.days)
+            UpdateBillItems.new('lala').perform
+          end
+
+          let(:bill_items) { BillItem.order(:id) }
+
+          it "splits out the trial period into a separate bill item" do
+            expect(bill_items.count).to eq 2
+            expect(bill_items.map(&:sells)).to eq ['any', 'any']
+            expect(bill_items.map(&:trial)).to eq [false, true]
+            expect(bill_items.map(&:begins_at)).to eq [start_of_july + 7.days, start_of_july + 10.days]
+            expect(bill_items.map(&:ends_at)).to eq [start_of_july + 10.days, start_of_july + 28.days]
+          end
+
+          it "splits the turnover for the month to date" do
+            expect(bill_items.first.turnover).to eq 0
+            expect(bill_items.last.turnover).to eq order2.total + order3.total
+          end
+        end
+      end
+
+      context "where the sells property of the enterprise has been altered within the current billing period" do
+        before do
+          Timecop.freeze(start_of_july + 10.days) do
+            # NOTE: Sells is changed between when order1 and order2 are placed
+            enterprise.update_attribute(:sells, 'own')
+          end
+
+          Timecop.travel(start_of_july + 28.days)
+        end
+
+        after do
+          Timecop.return
+        end
+
+        context "where no trial information has been set" do
+          before do
+            UpdateBillItems.new('lala').perform
+          end
+
+          let(:bill_items) { BillItem.order(:id) }
+
+          it "splits the billing period into a separate item for each sells value" do
+            expect(bill_items.count).to eq 2
+            expect(bill_items.map(&:sells)).to eq ['any', 'own']
+            expect(bill_items.map(&:trial)).to eq [false, false]
+            expect(bill_items.map(&:begins_at)).to eq [start_of_july + 7.days, start_of_july + 10.days]
+            expect(bill_items.map(&:ends_at)).to eq [start_of_july + 10.days, start_of_july + 28.days]
+          end
+
+          it "splits the turnover for the month to date" do
+            expect(bill_items.first.turnover).to eq 0
+            expect(bill_items.last.turnover).to eq order2.total + order3.total
+          end
+        end
+
+        context "where a trial ended during the current billing period, after sells was changed" do
+          before do
+            enterprise.update_attribute(:shop_trial_start_date, start_of_july - 10.days)
+            UpdateBillItems.new('lala').perform
+          end
+
+          let(:bill_items) { BillItem.order(:id) }
+
+          it "splits out the distinct sells periods and trial period into separate bill items" do
+            expect(bill_items.count).to eq 3
+            expect(bill_items.map(&:sells)).to eq ['any', 'own', 'own']
+            expect(bill_items.map(&:trial)).to eq [true, true, false]
+            expect(bill_items.map(&:begins_at)).to eq [start_of_july + 7.days, start_of_july + 10.days, start_of_july + 20.days]
+            expect(bill_items.map(&:ends_at)).to eq [start_of_july + 10.days, start_of_july + 20.days, start_of_july + 28.days]
+          end
+
+          it "splits out the trial period into a separate bill item" do
+            expect(bill_items.first.turnover).to eq 0
+            expect(bill_items.second.turnover).to eq order2.total
+            expect(bill_items.last.turnover).to eq order3.total
+          end
+        end
+
+        context "where a trial ended during the current billing period, before sells was changed" do
+          before do
+            enterprise.update_attribute(:shop_trial_start_date, start_of_july - 22.days)
+            UpdateBillItems.new('lala').perform
+          end
+
+          let(:bill_items) { BillItem.order(:id) }
+
+          it "splits out the distinct sells periods and trial period into separate bill items" do
+            expect(bill_items.count).to eq 3
+            expect(bill_items.map(&:sells)).to eq ['any', 'any', 'own']
+            expect(bill_items.map(&:trial)).to eq [true, false, false]
+            expect(bill_items.map(&:begins_at)).to eq [start_of_july + 7.days, start_of_july + 8.days, start_of_july + 10.days]
+            expect(bill_items.map(&:ends_at)).to eq [start_of_july + 8.days, start_of_july + 10.days, start_of_july + 28.days]
+          end
+
+          it "splits out the trial period into a separate bill item" do
+            expect(bill_items.first.turnover).to eq 0
+            expect(bill_items.second.turnover).to eq 0
+            expect(bill_items.last.turnover).to eq (order2.total + order3.total)
+          end
+        end
+
+        context "where the trial began part-way through the current billing period, after sells was changed" do
+          before do
+            enterprise.update_attribute(:shop_trial_start_date, start_of_july + 18.days)
+            UpdateBillItems.new('lala').perform
+          end
+
+          let(:bill_items) { BillItem.order(:id) }
+
+          it "splits out the distinct sells periods and trial period into separate bill items" do
+            expect(bill_items.count).to eq 3
+            expect(bill_items.map(&:sells)).to eq ['any', 'own', 'own']
+            expect(bill_items.map(&:trial)).to eq [false, false, true]
+            expect(bill_items.map(&:begins_at)).to eq [start_of_july + 7.days, start_of_july + 10.days, start_of_july + 18.days]
+            expect(bill_items.map(&:ends_at)).to eq [start_of_july + 10.days, start_of_july + 18.days, start_of_july + 28.days]
+          end
+
+          it "splits out the trial period into a separate bill item" do
+            expect(bill_items.first.turnover).to eq 0
+            expect(bill_items.second.turnover).to eq order2.total
+            expect(bill_items.last.turnover).to eq order3.total
+          end
+        end
+
+        context "where the trial began part-way through the current billing period, before sells was changed" do
+          before do
+            enterprise.update_attribute(:shop_trial_start_date, start_of_july + 8.days)
+            UpdateBillItems.new('lala').perform
+          end
+
+          let(:bill_items) { BillItem.order(:id) }
+
+          it "splits out the distinct sells periods and trial period into separate bill items" do
+            expect(bill_items.count).to eq 3
+            expect(bill_items.map(&:sells)).to eq ['any', 'any', 'own']
+            expect(bill_items.map(&:trial)).to eq [false, true, true]
+            expect(bill_items.map(&:begins_at)).to eq [start_of_july + 7.days, start_of_july + 8.days, start_of_july + 10.days]
+            expect(bill_items.map(&:ends_at)).to eq [start_of_july + 8.days, start_of_july + 10.days, start_of_july + 28.days]
+          end
+
+          it "splits out the trial period into a separate bill item" do
+            expect(bill_items.first.turnover).to eq 0
+            expect(bill_items.second.turnover).to eq 0
+            expect(bill_items.last.turnover).to eq (order2.total + order3.total)
+          end
+        end
+      end
     end
   end
-
-
 end