diff --git a/app/controllers/administrate/application_controller.rb b/app/controllers/administrate/application_controller.rb
index fba98788b1..90a50385a1 100644
--- a/app/controllers/administrate/application_controller.rb
+++ b/app/controllers/administrate/application_controller.rb
@@ -67,8 +67,11 @@ def update
     end
 
     def destroy
-      requested_resource.destroy
-      flash[:notice] = translate_with_resource("destroy.success")
+      if requested_resource.destroy
+        flash[:notice] = translate_with_resource("destroy.success")
+      else
+        flash[:error] = requested_resource.errors.full_messages.join("<br/>")
+      end
       redirect_to action: :index
     end
 
diff --git a/app/views/administrate/application/_flashes.html.erb b/app/views/administrate/application/_flashes.html.erb
index 07d4265222..61de271183 100644
--- a/app/views/administrate/application/_flashes.html.erb
+++ b/app/views/administrate/application/_flashes.html.erb
@@ -14,7 +14,7 @@ This partial renders flash messages on every page.
 <% if flash.any? %>
   <div class="flashes">
     <% flash.each do |key, value| -%>
-      <div class="flash flash-<%= key %>"><%= value %></div>
+      <div class="flash flash-<%= key %>"><%= value.html_safe %></div>
     <% end -%>
   </div>
 <% end %>
diff --git a/spec/example_app/app/models/order.rb b/spec/example_app/app/models/order.rb
index 5833f20c36..ded4bba9d2 100644
--- a/spec/example_app/app/models/order.rb
+++ b/spec/example_app/app/models/order.rb
@@ -3,7 +3,7 @@ class Order < ActiveRecord::Base
 
   validates :customer, presence: true
   has_many :line_items, dependent: :destroy
-  has_many :payments, dependent: :destroy
+  has_many :payments, dependent: :restrict_with_error
 
   validates :address_line_one, presence: true
   validates :address_line_two, presence: true
diff --git a/spec/features/orders_index_spec.rb b/spec/features/orders_index_spec.rb
index b300330d42..223dcb3029 100644
--- a/spec/features/orders_index_spec.rb
+++ b/spec/features/orders_index_spec.rb
@@ -55,4 +55,15 @@
       t("administrate.controller.destroy.success", resource: "Order")
     )
   end
+
+  scenario "cannot delete because associated payment" do
+    create(:payment, order: create(:order))
+
+    visit admin_orders_path
+    click_on t("administrate.actions.destroy")
+
+    expect(page).to have_flash(
+      "Cannot delete record because dependent payments exist", type: :error
+    )
+  end
 end
diff --git a/spec/models/order_spec.rb b/spec/models/order_spec.rb
index 62ada4434c..35de01b97a 100644
--- a/spec/models/order_spec.rb
+++ b/spec/models/order_spec.rb
@@ -24,6 +24,17 @@
     expect(LineItem.all).to be_empty
   end
 
+  it "raise error when try delete associated payment" do
+    order = create(:order)
+    create(:payment, order: order)
+
+    order.destroy
+
+    expect(order.errors[:base]).to eq(
+      ["Cannot delete record because dependent payments exist"],
+    )
+  end
+
   describe "#total_price" do
     it "returns 0 when there are no line items" do
       order = build(:order)
diff --git a/spec/support/have_flash_matcher.rb b/spec/support/have_flash_matcher.rb
index 8717a59be2..2e10dd723a 100644
--- a/spec/support/have_flash_matcher.rb
+++ b/spec/support/have_flash_matcher.rb
@@ -1,5 +1,6 @@
 module Features
-  def have_flash(text)
-    have_css(".flash-notice", text: text)
+  def have_flash(text, options = {})
+    options.reverse_merge!(type: :notice)
+    have_css(".flash-#{options[:type]}", text: text)
   end
 end