diff --git a/db/migrate/20140826043521_prevent_duplicate_enterprise_roles.rb b/db/migrate/20140826043521_prevent_duplicate_enterprise_roles.rb
new file mode 100644
index 0000000000..5b4fc6e7fc
--- /dev/null
+++ b/db/migrate/20140826043521_prevent_duplicate_enterprise_roles.rb
@@ -0,0 +1,5 @@
+class PreventDuplicateEnterpriseRoles < ActiveRecord::Migration
+  def change
+    add_index :enterprise_roles, [:enterprise_id, :user_id], unique: true
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 316c341576..dbb50d6b33 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -11,7 +11,7 @@
 #
 # It's strongly recommended to check this file into your version control system.
 
-ActiveRecord::Schema.define(:version => 20140825023227) do
+ActiveRecord::Schema.define(:version => 20140826043521) do
 
   create_table "adjustment_metadata", :force => true do |t|
     t.integer "adjustment_id"
@@ -228,6 +228,7 @@ ActiveRecord::Schema.define(:version => 20140825023227) do
     t.integer "enterprise_id"
   end
 
+  add_index "enterprise_roles", ["enterprise_id", "user_id"], :name => "index_enterprise_roles_on_enterprise_id_and_user_id", :unique => true
   add_index "enterprise_roles", ["enterprise_id"], :name => "index_enterprise_roles_on_enterprise_id"
   add_index "enterprise_roles", ["user_id", "enterprise_id"], :name => "index_enterprise_roles_on_user_id_and_enterprise_id", :unique => true
   add_index "enterprise_roles", ["user_id"], :name => "index_enterprise_roles_on_user_id"
@@ -562,9 +563,9 @@ ActiveRecord::Schema.define(:version => 20140825023227) do
     t.string   "email"
     t.text     "special_instructions"
     t.integer  "distributor_id"
+    t.integer  "order_cycle_id"
     t.string   "currency"
     t.string   "last_ip_address"
-    t.integer  "order_cycle_id"
     t.integer  "cart_id"
   end