diff --git a/app/assets/javascripts/admin/enterprises/directives/terms_and_conditions_warning.js.coffee b/app/assets/javascripts/admin/enterprises/directives/terms_and_conditions_warning.js.coffee
new file mode 100644
index 0000000000..d8aafe113d
--- /dev/null
+++ b/app/assets/javascripts/admin/enterprises/directives/terms_and_conditions_warning.js.coffee
@@ -0,0 +1,30 @@
+angular.module("admin.enterprises").directive 'termsAndConditionsWarning', ($compile, $templateCache, DialogDefaults, $timeout) ->
+  restrict: 'A'
+  scope: true
+
+  link: (scope, element, attr) ->
+    # This file input click handler will hold the browser file input dialog and show a warning modal
+    scope.hold_file_input_and_show_warning_modal = (event) ->
+      event.preventDefault()
+      scope.template = $compile($templateCache.get('admin/modals/terms_and_conditions_warning.html'))(scope)
+      if scope.template.dialog
+        scope.template.dialog(DialogDefaults)
+        scope.template.dialog('open')
+      scope.$apply()
+
+    element.bind 'click', scope.hold_file_input_and_show_warning_modal
+
+    # When the user presses continue in the warning modal, we open the browser file input dialog
+    scope.continue = ->
+      scope.template.dialog('close')
+
+      # unbind warning modal handler and click file input again to open the browser file input dialog
+      element.unbind('click').trigger('click')
+      # afterwards, bind warning modal handler again so that the warning is shown the next time
+      $timeout ->
+        element.bind 'click', scope.hold_file_input_and_show_warning_modal
+      return
+
+    scope.close = ->
+      scope.template.dialog('close')
+      return
diff --git a/app/assets/javascripts/darkswarm/services/checkout.js.coffee b/app/assets/javascripts/darkswarm/services/checkout.js.coffee
index 69c484ccb4..ef865012c2 100644
--- a/app/assets/javascripts/darkswarm/services/checkout.js.coffee
+++ b/app/assets/javascripts/darkswarm/services/checkout.js.coffee
@@ -95,6 +95,10 @@ Darkswarm.factory 'Checkout', ($injector, CurrentOrder, ShippingMethods, StripeE
               last_name: @order.bill_address.lastname
               save_requested_by_customer: @secrets.save_requested_by_customer
           }
+
+      if @terms_and_conditions_accepted()
+        munged_order["terms_and_conditions_accepted"] = true
+
       munged_order
 
     shippingMethod: ->
@@ -114,3 +118,7 @@ Darkswarm.factory 'Checkout', ($injector, CurrentOrder, ShippingMethods, StripeE
 
     cartTotal: ->
       @order.display_total + @shippingPrice() + @paymentPrice()
+
+    terms_and_conditions_accepted: ->
+      terms_and_conditions_checkbox = angular.element("#accept_terms")[0]
+      terms_and_conditions_checkbox? && terms_and_conditions_checkbox.checked
diff --git a/app/assets/javascripts/templates/admin/modals/terms_and_conditions_info.html.haml b/app/assets/javascripts/templates/admin/modals/terms_and_conditions_info.html.haml
new file mode 100644
index 0000000000..5a3568085e
--- /dev/null
+++ b/app/assets/javascripts/templates/admin/modals/terms_and_conditions_info.html.haml
@@ -0,0 +1,13 @@
+%div
+  .margin-bottom-30.text-center
+    .text-big
+      {{ 'js.admin.modals.terms_and_conditions_info.title' | t }}
+  .margin-bottom-30
+    %p
+      {{ 'js.admin.modals.terms_and_conditions_info.message_1' | t }}
+  .margin-bottom-30
+    %p
+      {{ 'js.admin.modals.terms_and_conditions_info.message_2' | t }}
+
+  .text-center
+    %input.button.red.icon-plus{ type: 'button', value: t('js.admin.modals.got_it'), ng: { click: 'close()' } }
diff --git a/app/assets/javascripts/templates/admin/modals/terms_and_conditions_warning.html.haml b/app/assets/javascripts/templates/admin/modals/terms_and_conditions_warning.html.haml
new file mode 100644
index 0000000000..13eed6fe85
--- /dev/null
+++ b/app/assets/javascripts/templates/admin/modals/terms_and_conditions_warning.html.haml
@@ -0,0 +1,14 @@
+%div
+  .margin-bottom-30.text-center
+    .text-big
+      {{ 'js.admin.modals.terms_and_conditions_warning.title' | t }}
+  .margin-bottom-30
+    %p
+      {{ 'js.admin.modals.terms_and_conditions_warning.message_1' | t }}
+  .margin-bottom-30
+    %p
+      {{ 'js.admin.modals.terms_and_conditions_warning.message_2' | t }}
+
+  .text-center
+    %input.button.red{ type: 'button', value: t('js.admin.modals.close'), ng: { click: 'close()' } }
+    %input.button.red{ type: 'button', value: t('js.admin.modals.continue'), ng: { click: 'continue()' } }
diff --git a/app/helpers/terms_and_conditions_helper.rb b/app/helpers/terms_and_conditions_helper.rb
new file mode 100644
index 0000000000..ef50459edb
--- /dev/null
+++ b/app/helpers/terms_and_conditions_helper.rb
@@ -0,0 +1,16 @@
+# frozen_string_literal: true
+
+module TermsAndConditionsHelper
+  def terms_and_conditions_activated?
+    current_order.distributor.terms_and_conditions.file?
+  end
+
+  def terms_and_conditions_already_accepted?
+    customer_terms_and_conditions_accepted_at = spree_current_user&.
+      customer_of(current_order.distributor)&.terms_and_conditions_accepted_at
+
+    customer_terms_and_conditions_accepted_at.present? &&
+      (customer_terms_and_conditions_accepted_at >
+        current_order.distributor.terms_and_conditions_updated_at)
+  end
+end
diff --git a/app/serializers/api/admin/enterprise_serializer.rb b/app/serializers/api/admin/enterprise_serializer.rb
index 2385d996d6..399284d132 100644
--- a/app/serializers/api/admin/enterprise_serializer.rb
+++ b/app/serializers/api/admin/enterprise_serializer.rb
@@ -6,7 +6,8 @@ class Api::Admin::EnterpriseSerializer < ActiveModel::Serializer
              :preferred_product_selection_from_inventory_only,
              :preferred_show_customer_names_to_suppliers, :owner, :contact, :users, :tag_groups,
              :default_tag_group, :require_login, :allow_guest_orders, :allow_order_changes,
-             :logo, :promo_image, :terms_and_conditions, :terms_and_conditions_file_name
+             :logo, :promo_image, :terms_and_conditions,
+             :terms_and_conditions_file_name, :terms_and_conditions_updated_at
 
   has_one :owner, serializer: Api::Admin::UserSerializer
   has_many :users, serializer: Api::Admin::UserSerializer
@@ -21,9 +22,13 @@ class Api::Admin::EnterpriseSerializer < ActiveModel::Serializer
   end
 
   def terms_and_conditions
-    return unless @object.terms_and_conditions.file?
+    return unless object.terms_and_conditions.file?
 
-    @object.terms_and_conditions.url
+    object.terms_and_conditions.url
+  end
+
+  def terms_and_conditions_updated_at
+    object.terms_and_conditions_updated_at&.to_s
   end
 
   def tag_groups
diff --git a/app/services/checkout/post_checkout_actions.rb b/app/services/checkout/post_checkout_actions.rb
index f595ab0537..c9defcc9ca 100644
--- a/app/services/checkout/post_checkout_actions.rb
+++ b/app/services/checkout/post_checkout_actions.rb
@@ -8,6 +8,7 @@ module Checkout
     end
 
     def success(controller, params, current_user)
+      set_customer_terms_and_conditions_accepted_at(params)
       save_order_addresses_as_user_default(params, current_user)
       OrderCompletionReset.new(controller, @order).call
     end
@@ -26,5 +27,11 @@ module Checkout
       user_default_address_setter.set_default_bill_address if params[:order][:default_bill_address]
       user_default_address_setter.set_default_ship_address if params[:order][:default_ship_address]
     end
+
+    def set_customer_terms_and_conditions_accepted_at(params)
+      return unless params[:order]
+
+      @order.customer.update(terms_and_conditions_accepted_at: Time.zone.now) if params[:order][:terms_and_conditions_accepted]
+    end
   end
 end
diff --git a/app/views/admin/enterprises/form/_business_details.html.haml b/app/views/admin/enterprises/form/_business_details.html.haml
index d15e3803c0..1bade5b580 100644
--- a/app/views/admin/enterprises/form/_business_details.html.haml
+++ b/app/views/admin/enterprises/form/_business_details.html.haml
@@ -35,12 +35,15 @@
 .row
   .alpha.three.columns
     = f.label :terms_and_conditions, t('.terms_and_conditions')
+    %i.text-big.icon-question-sign.help-modal{ template: 'admin/modals/terms_and_conditions_info.html' }
 
   .omega.eight.columns
-    %a{ href: '{{ Enterprise.terms_and_conditions }}', ng: { if: 'Enterprise.terms_and_conditions' } }
+    %a{ href: '{{ Enterprise.terms_and_conditions }}', target: '_blank', ng: { if: 'Enterprise.terms_and_conditions' } }
       = '{{ Enterprise.terms_and_conditions_file_name }}'
+      = t('.uploaded_on')
+      = '{{ Enterprise.terms_and_conditions_updated_at }}'
     .pad-top
-      = f.file_field :terms_and_conditions
+      = f.file_field :terms_and_conditions, accept: 'application/pdf', 'terms-and-conditions-warning' => 'true'
     .pad-top
       %a.button.red{ href: '', ng: {click: 'removeTermsAndConditions()', if: 'Enterprise.terms_and_conditions'} }
         = t('.remove_terms_and_conditions')
diff --git a/app/views/checkout/_form.html.haml b/app/views/checkout/_form.html.haml
index f341a666d9..e755af01e4 100644
--- a/app/views/checkout/_form.html.haml
+++ b/app/views/checkout/_form.html.haml
@@ -16,6 +16,6 @@
   = render "checkout/already_ordered", f: f if show_bought_items?
   = render "checkout/terms_and_conditions", f: f
   %p
-    %button.button.primary{type: :submit}
+    %button.button.primary{ type: :submit, ng: { disabled: "terms_and_conditions_activated && !terms_and_conditions_accepted" } }
       = t :checkout_send
     / {{ checkout.$valid }}
diff --git a/app/views/checkout/_terms_and_conditions.html.haml b/app/views/checkout/_terms_and_conditions.html.haml
index a99cf44785..05e0122ae7 100644
--- a/app/views/checkout/_terms_and_conditions.html.haml
+++ b/app/views/checkout/_terms_and_conditions.html.haml
@@ -1,2 +1,4 @@
-%p.small
-  = t('.message_html', terms_and_conditions_link: link_to( t( '.link_text' ), current_order.distributor.terms_and_conditions.url, target: '_blank')) if current_order.distributor.terms_and_conditions.file?
+- if terms_and_conditions_activated?
+  %p
+    %input{ type: 'checkbox', id: 'accept_terms', ng: { model: "terms_and_conditions_accepted", init: "terms_and_conditions_activated=#{terms_and_conditions_activated?}; terms_and_conditions_accepted=#{terms_and_conditions_already_accepted?}" } }
+      %label.small{for: "accept_terms"}= t('.message_html', terms_and_conditions_link: link_to( t( '.link_text' ), current_order.distributor.terms_and_conditions.url, target: '_blank'))
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 8b9786f1e9..ed2261fcf4 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -705,6 +705,7 @@ en:
           invoice_text: Add customized text at the end of invoices
           terms_and_conditions: "Terms and Conditions"
           remove_terms_and_conditions: "Remove File"
+          uploaded_on: "uploaded on"
         contact:
           name: Name
           name_placeholder: eg. Gustav Plum
@@ -1235,8 +1236,8 @@ en:
       cart: "cart"
       message_html: "You have an order for this order cycle already. Check the %{cart} to see the items you ordered before. You can also cancel items as long as the order cycle is open."
     terms_and_conditions:
-      message_html: "By placing this order you agree to the %{terms_and_conditions_link}."
-      link_text: "Terms of Service"
+      message_html: "I agree to the seller's %{terms_and_conditions_link}."
+      link_text: "Terms and Conditions"
     failed: "The checkout failed. Please let us know so that we can process your order."
   shops:
     hubs:
@@ -2517,8 +2518,9 @@ See the %{link} to find out more about %{sitename}'s features and to start using
     admin:
       enterprise_limit_reached: "You have reached the standard limit of enterprises per account. Write to %{contact_email} if you need to increase it."
       modals:
-        got_it: Got it
+        got_it: "Got it"
         close: "Close"
+        continue: "Continue"
         invite: "Invite"
         invite_title: "Invite an unregistered user"
         tag_rule_help:
@@ -2537,6 +2539,14 @@ See the %{link} to find out more about %{sitename}'s features and to start using
           customer_tagged_rules_text: >
             By creating rules related to a specific customer tag, you can override the default
             behaviour (whether it be to show or to hide items) for customers with the specified tag.
+        terms_and_conditions_info:
+          title: "Uploading Terms and Conditions"
+          message_1: "Terms and Conditions are the contract between you, the seller, and the shopper. If you upload a file here shoppers must accept your Terms and Conditions in order to complete checkout. For the shopper this will appear as a checkbox at checkout that must be checked in order to proceed with checkout. We highly recommend you upload Terms and Conditions in alignment with national legislation."
+          message_2: "Shoppers will only be required to accept Terms and Conditions once. However if you change you Terms and Conditions shoppers will again be required to accept them before they can checkout."
+        terms_and_conditions_warning:
+          title: "Uploading Terms and Conditions"
+          message_1: "All your buyers will have to agree to them once at checkout. If you update the file, all your buyers will have to agree to them again at checkout."
+          message_2: "For buyers with subscriptions, you need to email them the Terms and Conditions (or the changes to them) for now, nothing will notify them about these new Terms and Conditions."
       panels:
         save: SAVE
         saved: SAVED
diff --git a/db/migrate/20200907140555_add_customer_terms_and_conditions_accepted.rb b/db/migrate/20200907140555_add_customer_terms_and_conditions_accepted.rb
new file mode 100644
index 0000000000..c48b1c19f2
--- /dev/null
+++ b/db/migrate/20200907140555_add_customer_terms_and_conditions_accepted.rb
@@ -0,0 +1,5 @@
+class AddCustomerTermsAndConditionsAccepted < ActiveRecord::Migration
+  def change
+    add_column :customers, :terms_and_conditions_accepted_at, :datetime
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 5f982a1216..30247daf3a 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -47,16 +47,17 @@ ActiveRecord::Schema.define(version: 20200912190210) do
   add_index "coordinator_fees", ["order_cycle_id"], name: "index_coordinator_fees_on_order_cycle_id", using: :btree
 
   create_table "customers", force: true do |t|
-    t.string   "email",                           null: false
-    t.integer  "enterprise_id",                   null: false
+    t.string   "email",                                            null: false
+    t.integer  "enterprise_id",                                    null: false
     t.string   "code"
     t.integer  "user_id"
-    t.datetime "created_at",                      null: false
-    t.datetime "updated_at",                      null: false
+    t.datetime "created_at",                                       null: false
+    t.datetime "updated_at",                                       null: false
     t.integer  "bill_address_id"
     t.integer  "ship_address_id"
     t.string   "name"
-    t.boolean  "allow_charges",   default: false, null: false
+    t.boolean  "allow_charges",                    default: false, null: false
+    t.datetime "terms_and_conditions_accepted_at"
   end
 
   add_index "customers", ["bill_address_id"], name: "index_customers_on_bill_address_id", using: :btree
diff --git a/lib/tasks/sample_data/order_factory.rb b/lib/tasks/sample_data/order_factory.rb
index 9614f685a0..cdb2dfcc4e 100644
--- a/lib/tasks/sample_data/order_factory.rb
+++ b/lib/tasks/sample_data/order_factory.rb
@@ -57,7 +57,7 @@ class OrderFactory
       bill_address: order_address,
       ship_address: order_address
     )
-    order.line_items.create( variant_id: first_variant.id, quantity: 5 )
+    order.line_items.create(variant_id: first_variant.id, quantity: 5)
     order.payments.create(payment_method_id: first_payment_method_id)
     order
   end
diff --git a/spec/features/admin/enterprises/terms_and_conditions_spec.rb b/spec/features/admin/enterprises/terms_and_conditions_spec.rb
index ced7c5deea..476ea6eaad 100644
--- a/spec/features/admin/enterprises/terms_and_conditions_spec.rb
+++ b/spec/features/admin/enterprises/terms_and_conditions_spec.rb
@@ -16,7 +16,7 @@ feature "Uploading Terms and Conditions PDF" do
       visit edit_admin_enterprise_path(distributor)
     end
 
-    describe "images for an enterprise" do
+    describe "with terms and conditions to upload" do
       def go_to_business_details
         within(".side_menu") do
           click_link "Business Details"
@@ -43,21 +43,27 @@ feature "Uploading Terms and Conditions PDF" do
 
         # Add PDF
         attach_file "enterprise[terms_and_conditions]", white_pdf_file_name
-        click_button "Update"
+
+        Timecop.freeze(run_time = Time.zone.local(2002, 4, 13, 0, 0, 0)) do
+          click_button "Update"
+          expect(distributor.reload.terms_and_conditions_updated_at).to eq run_time
+        end
         expect(page).
-          to have_content("Enterprise \"#{distributor.name}\" has been successfully updated!")
+          to have_content "Enterprise \"#{distributor.name}\" has been successfully updated!"
 
         go_to_business_details
-        expect(page).to have_selector("a[href*='logo-white.pdf']")
+        expect(page).to have_selector "a[href*='logo-white.pdf'][target=\"_blank\"]"
+        expect(page).to have_content "2002-04-13 00:00:00 +1000"
 
         # Replace PDF
         attach_file "enterprise[terms_and_conditions]", black_pdf_file_name
         click_button "Update"
         expect(page).
-          to have_content("Enterprise \"#{distributor.name}\" has been successfully updated!")
+          to have_content "Enterprise \"#{distributor.name}\" has been successfully updated!"
+        expect(distributor.reload.terms_and_conditions_updated_at).to_not eq run_time
 
         go_to_business_details
-        expect(page).to have_selector("a[href*='logo-black.pdf']")
+        expect(page).to have_selector "a[href*='logo-black.pdf']"
       end
     end
   end
diff --git a/spec/features/consumer/shopping/checkout_spec.rb b/spec/features/consumer/shopping/checkout_spec.rb
index 26be7c62a5..bedabaa2c3 100644
--- a/spec/features/consumer/shopping/checkout_spec.rb
+++ b/spec/features/consumer/shopping/checkout_spec.rb
@@ -122,11 +122,11 @@ feature "As a consumer I want to check out my cart", js: true do
       end
 
       it "doesn't show link to terms and conditions" do
-        expect(page).to have_no_link("Terms of Service")
+        expect(page).to have_no_link("Terms and Conditions")
       end
     end
 
-    context "when distributor has terms and conditions" do
+    context "when distributor has T&Cs" do
       let(:fake_terms_and_conditions_path) { Rails.root.join("app/assets/images/logo-white.png") }
       let(:terms_and_conditions_file) { Rack::Test::UploadedFile.new(fake_terms_and_conditions_path, "application/pdf") }
 
@@ -135,9 +135,37 @@ feature "As a consumer I want to check out my cart", js: true do
         order.distributor.save
       end
 
-      it "shows a link to the terms and conditions" do
-        visit checkout_path
-        expect(page).to have_link("Terms of Service", href: order.distributor.terms_and_conditions.url)
+      describe "when customer has not accepted T&Cs before" do
+        it "shows a link to the T&Cs and disables checkout button until terms are accepted" do
+          visit checkout_path
+          expect(page).to have_link("Terms and Conditions", href: order.distributor.terms_and_conditions.url)
+
+          expect(page).to have_button("Place order now", disabled: true)
+
+          check "accept_terms"
+          expect(page).to have_button("Place order now", disabled: false)
+        end
+      end
+
+      describe "when customer has already accepted T&Cs before" do
+        before do
+          customer = create(:customer, enterprise: order.distributor, user: user)
+          customer.update terms_and_conditions_accepted_at: Time.zone.now
+        end
+
+        it "enables checkout button (because T&Cs are accepted by default)" do
+          visit checkout_path
+          expect(page).to have_button("Place order now", disabled: false)
+        end
+
+        describe "but afterwards the enterprise has uploaded a new T&Cs file" do
+          before { order.distributor.update terms_and_conditions_updated_at: Time.zone.now }
+
+          it "disables checkout button until terms are accepted" do
+            visit checkout_path
+            expect(page).to have_button("Place order now", disabled: true)
+          end
+        end
       end
     end
 
diff --git a/spec/javascripts/unit/admin/enterprises/directives/terms_and_conditions_warning_spec.js.coffee b/spec/javascripts/unit/admin/enterprises/directives/terms_and_conditions_warning_spec.js.coffee
new file mode 100644
index 0000000000..b7647024e2
--- /dev/null
+++ b/spec/javascripts/unit/admin/enterprises/directives/terms_and_conditions_warning_spec.js.coffee
@@ -0,0 +1,18 @@
+describe "termsAndConditionsWarning", ->
+  element = null
+  templatecache = null
+
+  beforeEach ->
+    module('admin.enterprises')
+
+    inject ($rootScope, $compile, $templateCache) ->
+      templatecache = $templateCache
+      el = angular.element("<input terms-and-conditions-warning=\"true\"></input>")
+      element = $compile(el)($rootScope)
+      $rootScope.$digest()
+
+  describe "terms and conditions warning", ->
+    it "should load template", ->
+      spyOn(templatecache, 'get')
+      element.triggerHandler('click');
+      expect(templatecache.get).toHaveBeenCalledWith('admin/modals/terms_and_conditions_warning.html')
diff --git a/spec/javascripts/unit/darkswarm/services/checkout_spec.js.coffee b/spec/javascripts/unit/darkswarm/services/checkout_spec.js.coffee
index 8caacdc531..8c5d49633b 100644
--- a/spec/javascripts/unit/darkswarm/services/checkout_spec.js.coffee
+++ b/spec/javascripts/unit/darkswarm/services/checkout_spec.js.coffee
@@ -65,6 +65,7 @@ describe 'Checkout service', ->
     inject ($injector, _$httpBackend_, $rootScope)->
       $httpBackend = _$httpBackend_
       Checkout = $injector.get("Checkout")
+      spyOn(Checkout, "terms_and_conditions_accepted")
       scope = $rootScope.$new()
       scope.Checkout = Checkout
       Navigation = $injector.get("Navigation")
diff --git a/spec/services/checkout/post_checkout_actions_spec.rb b/spec/services/checkout/post_checkout_actions_spec.rb
index 916cff69fb..4c5ee6a1c2 100644
--- a/spec/services/checkout/post_checkout_actions_spec.rb
+++ b/spec/services/checkout/post_checkout_actions_spec.rb
@@ -23,6 +23,21 @@ describe Checkout::PostCheckoutActions do
       postCheckoutActions.success(controller, params, current_user)
     end
 
+    describe "setting customer terms_and_conditions_accepted_at" do
+      before { order.customer = build(:customer) }
+
+      it "does not set customer's terms_and_conditions to the current time if terms have not been accepted" do
+        postCheckoutActions.success(controller, params, current_user)
+        expect(order.customer.terms_and_conditions_accepted_at).to be_nil
+      end
+
+      it "sets customer's terms_and_conditions to the current time if terms have been accepted" do
+        params = { order: { terms_and_conditions_accepted: true } }
+        postCheckoutActions.success(controller, params, current_user)
+        expect(order.customer.terms_and_conditions_accepted_at).to_not be_nil
+      end
+    end
+
     describe "setting the user default address" do
       let(:user_default_address_setter) { instance_double(UserDefaultAddressSetter) }