diff --git a/app/assets/javascripts/darkswarm/controllers/cart_form_controller.js.coffee b/app/assets/javascripts/darkswarm/controllers/cart_form_controller.js.coffee
new file mode 100644
index 0000000000..73fe91793f
--- /dev/null
+++ b/app/assets/javascripts/darkswarm/controllers/cart_form_controller.js.coffee
@@ -0,0 +1,2 @@
+Darkswarm.controller "CartFormCtrl", ($scope) ->
+
diff --git a/app/assets/javascripts/darkswarm/directives/disable_dynamically.js.coffee b/app/assets/javascripts/darkswarm/directives/disable_dynamically.js.coffee
new file mode 100644
index 0000000000..7cff41f3f4
--- /dev/null
+++ b/app/assets/javascripts/darkswarm/directives/disable_dynamically.js.coffee
@@ -0,0 +1,12 @@
+# Allows disabling of link buttons via disabled attribute.
+# This is normally ignored, ie the link appears disabled but is still clickable.
+
+Darkswarm.directive "disableDynamically", ->
+  restrict: 'A'
+
+  link: (scope, element, attrs) ->
+    element.on 'click', (e) ->
+      if attrs.disabled
+        e.preventDefault()
+      return
+
diff --git a/app/assets/javascripts/darkswarm/directives/on_hand.js.coffee b/app/assets/javascripts/darkswarm/directives/on_hand.js.coffee
index 8ad5a8748a..66c20d86fb 100644
--- a/app/assets/javascripts/darkswarm/directives/on_hand.js.coffee
+++ b/app/assets/javascripts/darkswarm/directives/on_hand.js.coffee
@@ -1,4 +1,4 @@
-Darkswarm.directive "ofnOnHand", ->
+Darkswarm.directive "ofnOnHand", (StockQuantity) ->
   restrict: 'A'
   require: "ngModel"
   scope: true
@@ -24,6 +24,4 @@ Darkswarm.directive "ofnOnHand", ->
       viewValue
 
     scope.available_quantity = ->
-      on_hand = parseInt(attr.ofnOnHand)
-      finalized_quantity = parseInt(attr.finalizedquantity) || 0 # finalizedquantity is optional
-      on_hand + finalized_quantity
+      StockQuantity.available_quantity(attr.ofnOnHand, attr.finalizedquantity)
diff --git a/app/assets/javascripts/darkswarm/directives/validate_stock_quantity.js.coffee b/app/assets/javascripts/darkswarm/directives/validate_stock_quantity.js.coffee
new file mode 100644
index 0000000000..3ceee62a4d
--- /dev/null
+++ b/app/assets/javascripts/darkswarm/directives/validate_stock_quantity.js.coffee
@@ -0,0 +1,16 @@
+Darkswarm.directive "validateStockQuantity", (StockQuantity) ->
+  restrict: 'A'
+  require: "ngModel"
+  scope: true
+
+  link: (scope, element, attr, ngModel) ->
+    ngModel.$parsers.push (selectedQuantity) ->
+      valid_number = parseInt(selectedQuantity) != NaN
+      valid_quantity = parseInt(selectedQuantity) <= scope.available_quantity()
+
+      ngModel.$setValidity('stock', (valid_number && valid_quantity) );
+
+      selectedQuantity
+
+    scope.available_quantity = ->
+      StockQuantity.available_quantity(attr.ofnOnHand, attr.finalizedquantity)
diff --git a/app/assets/javascripts/darkswarm/services/stock_quantity.js.coffee b/app/assets/javascripts/darkswarm/services/stock_quantity.js.coffee
new file mode 100644
index 0000000000..efc6b67eb4
--- /dev/null
+++ b/app/assets/javascripts/darkswarm/services/stock_quantity.js.coffee
@@ -0,0 +1,7 @@
+Darkswarm.factory "StockQuantity", ->
+  new class StockQuantity
+    available_quantity: (on_hand, finalized_quantity) ->
+      on_hand = parseInt(on_hand)
+      finalized_quantity = parseInt(finalized_quantity) || 0 # finalized_quantity is optional
+
+      on_hand + finalized_quantity
diff --git a/app/assets/stylesheets/darkswarm/shopping-cart.css.scss b/app/assets/stylesheets/darkswarm/shopping-cart.css.scss
index bd4a5019c8..d00f3915e7 100644
--- a/app/assets/stylesheets/darkswarm/shopping-cart.css.scss
+++ b/app/assets/stylesheets/darkswarm/shopping-cart.css.scss
@@ -72,6 +72,12 @@
 }
 
 // Shopping cart
+#update-cart {
+  #errorExplanation {
+    display: none;
+  }
+}
+
 #cart-detail {
   .cart-item-delete, .bought-item-delete {
     a {
@@ -102,6 +108,12 @@
       float: right;
     }
   }
+
+  input {
+    &.ng-invalid-stock, &.ng-invalid-number {
+      border: 1px solid $clr-brick;
+    }
+  }
 }
 
 .item-thumb-image {
diff --git a/app/views/spree/orders/_line_item.html.haml b/app/views/spree/orders/_line_item.html.haml
index cfd4d4a500..918a520fdf 100644
--- a/app/views/spree/orders/_line_item.html.haml
+++ b/app/views/spree/orders/_line_item.html.haml
@@ -23,7 +23,11 @@
     = line_item.single_display_amount_with_adjustments.to_html
   %td.text-center.cart-item-quantity{"data-hook" => "cart_item_quantity"}
     - finalized_quantity = @order.completed? ? line_item.quantity : 0
-    = item_form.number_field :quantity, :min => 0, "ofn-on-hand" => "#{variant.on_demand && 9999 || variant.on_hand}", "finalizedquantity" => finalized_quantity, "ng-model" => "line_item_#{line_item.id}", :class => "line_item_quantity", :size => 5
+    = item_form.number_field :quantity,
+      :min => 0, "ofn-on-hand" => "#{variant.on_demand && 9999 || variant.on_hand}",
+      "finalizedquantity" => finalized_quantity, :class => "line_item_quantity", :size => 5,
+      "ng-model" => "line_item_#{line_item.id}",
+      "validate-stock-quantity" => true
   %td.cart-item-total.text-right{"data-hook" => "cart_item_total"}
     = line_item.display_amount_with_adjustments.to_html unless line_item.quantity.nil?
 
diff --git a/app/views/spree/orders/edit.html.haml b/app/views/spree/orders/edit.html.haml
index f654cfebb1..d9cdb977b3 100644
--- a/app/views/spree/orders/edit.html.haml
+++ b/app/views/spree/orders/edit.html.haml
@@ -33,7 +33,8 @@
 
     - else
       %div{"data-hook" => "outside_cart_form"}
-        = form_for @order, :url => main_app.update_cart_path, :html => {:id => 'update-cart'} do |order_form|
+        = form_for @order, :url => main_app.update_cart_path,
+          :html => {id: 'update-cart', name: "form", "ng-controller"=> 'CartFormCtrl'} do |order_form|
           %div{"data-hook" => "inside_cart_form"}
             %div{"data-hook" => "cart_items"}
               .row
diff --git a/app/views/spree/orders/form/_cart_actions_row.html.haml b/app/views/spree/orders/form/_cart_actions_row.html.haml
index ec3ce122ea..a7005a5eb6 100644
--- a/app/views/spree/orders/form/_cart_actions_row.html.haml
+++ b/app/views/spree/orders/form/_cart_actions_row.html.haml
@@ -1,7 +1,7 @@
 %tr
   %td{colspan:"2"}
   %td
-    = button_tag :class => 'secondary radius expand small', :id => 'update-button' do
+    %button#update-button.secondary.radius.expand.small{"ng-class" => "{ alert: form.$dirty && form.$valid }"}
       %i.ofn-i_023-refresh
       = t(:update)
   %td
diff --git a/app/views/spree/orders/form/_cart_links.html.haml b/app/views/spree/orders/form/_cart_links.html.haml
index 8da012cd78..798a428f7c 100644
--- a/app/views/spree/orders/form/_cart_links.html.haml
+++ b/app/views/spree/orders/form/_cart_links.html.haml
@@ -1,5 +1,5 @@
 .row.links{'data-hook' => "cart_buttons"}
-  %a.button.large.secondary{href: current_shop_products_path}
+  %a.continue-shopping.button.large.secondary{href: current_shop_products_path, "ng-disabled" => "#{@insufficient_stock_lines.any?}", "disable-dynamically" => true}
     = t :orders_edit_continue
-  %a#checkout-link.button.large.primary.right{href: main_app.checkout_path}
+  %a#checkout-link.button.large.primary.right{href: main_app.checkout_path, "ng-disabled" => "#{@insufficient_stock_lines.any?}", "disable-dynamically" => true}
     = t :orders_edit_checkout
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 601a916c02..1aee3bfa2c 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -3406,7 +3406,7 @@ See the %{link} to find out more about %{sitename}'s features and to start using
       format: ! '%Y-%m-%d'
       js_format: 'yy-mm-dd'
     orders:
-      error_flash_for_unavailable_items: "An item in your cart has become unavailable."
+      error_flash_for_unavailable_items: "An item in your cart has become unavailable. Please update the selected quantities."
       edit:
         login_to_view_order: "Please log in to view your order."
       bought:
diff --git a/spec/controllers/spree/orders_controller_spec.rb b/spec/controllers/spree/orders_controller_spec.rb
index c018a98873..783c868366 100644
--- a/spec/controllers/spree/orders_controller_spec.rb
+++ b/spec/controllers/spree/orders_controller_spec.rb
@@ -161,7 +161,7 @@ describe Spree::OrdersController, type: :controller do
         it "displays a flash message when we view the cart" do
           spree_get :edit
           expect(response.status).to eq 200
-          expect(flash[:error]).to eq("An item in your cart has become unavailable.")
+          expect(flash[:error]).to eq I18n.t('spree.orders.error_flash_for_unavailable_items')
         end
       end
 
@@ -173,7 +173,7 @@ describe Spree::OrdersController, type: :controller do
         it "displays a flash message when we view the cart" do
           spree_get :edit
           expect(response.status).to eq 200
-          expect(flash[:error]).to eq("An item in your cart has become unavailable.")
+          expect(flash[:error]).to eq I18n.t('spree.orders.error_flash_for_unavailable_items')
         end
       end
     end
diff --git a/spec/features/consumer/shopping/cart_spec.rb b/spec/features/consumer/shopping/cart_spec.rb
index 95a51ce1ec..9068504be6 100644
--- a/spec/features/consumer/shopping/cart_spec.rb
+++ b/spec/features/consumer/shopping/cart_spec.rb
@@ -213,6 +213,40 @@ feature "full-page cart", js: true do
           expect(page).to have_content "Insufficient stock available, only 2 remaining"
           expect(page).to have_field "order_line_items_attributes_0_quantity", with: '1'
         end
+
+        describe "full UX for correcting selected quantities with insufficient stock" do
+          before do
+            add_product_to_cart order, product_with_tax, quantity: 5
+            variant.update_attributes! on_hand: 4, on_demand: false
+          end
+
+          it "gives clear user feedback during the correcting process" do
+            visit main_app.cart_path
+
+            # shows a relevant Flash message
+            expect(page).to have_selector ".alert-box", text: I18n.t('spree.orders.error_flash_for_unavailable_items')
+
+            # "Continue Shopping" and "Checkout" buttons are disabled
+            expect(page).to have_selector "a.continue-shopping[disabled=disabled]"
+            expect(page).to have_selector "a#checkout-link[disabled=disabled]"
+
+            # Quantity field clearly marked as invalid and "Update" button is not highlighted
+            expect(page).to have_selector "#order_line_items_attributes_0_quantity.ng-invalid-stock"
+            expect(page).to_not have_selector "#update-button.alert"
+
+            fill_in "order_line_items_attributes_0_quantity", with: 4
+
+            # Quantity field not marked as invalid and "Update" button is highlighted after correction
+            expect(page).to_not have_selector "#order_line_items_attributes_0_quantity.ng-invalid-stock"
+            expect(page).to have_selector "#update-button.alert"
+
+            click_button I18n.t("update")
+
+            # "Continue Shopping" and "Checkout" buttons are not disabled after cart is updated
+            expect(page).to_not have_selector "a.continue-shopping[disabled=disabled]"
+            expect(page).to_not have_selector "a#checkout-link[disabled=disabled]"
+          end
+        end
       end
     end