diff --git a/app/models/optimized_image.rb b/app/models/optimized_image.rb
index 9f4149d2ae2..d745bc2d1b6 100644
--- a/app/models/optimized_image.rb
+++ b/app/models/optimized_image.rb
@@ -36,6 +36,18 @@ class OptimizedImage < ActiveRecord::Base
     thumbnail
   end
 
+  def destroy
+    OptimizedImage.transaction do
+      remove_file
+      super
+    end
+  end
+
+  def remove_file
+    File.delete path
+  rescue Errno::ENOENT
+  end
+
   def url
     "#{Upload.base_url}/#{optimized_path}/#{filename}"
   end
diff --git a/app/models/upload.rb b/app/models/upload.rb
index f935e924101..6257f0653ea 100644
--- a/app/models/upload.rb
+++ b/app/models/upload.rb
@@ -11,7 +11,7 @@ class Upload < ActiveRecord::Base
   has_many :post_uploads
   has_many :posts, through: :post_uploads
 
-  has_many :optimized_images
+  has_many :optimized_images, dependent: :destroy
 
   validates_presence_of :filesize
   validates_presence_of :original_filename
@@ -36,7 +36,7 @@ class Upload < ActiveRecord::Base
     optimized_images << thumbnail if thumbnail
   end
 
-  def delete
+  def destroy
     Upload.transaction do
       Upload.remove_file url
       super
diff --git a/lib/tasks/images.rake b/lib/tasks/images.rake
index 4fcac3e67e9..c8d15eebc89 100644
--- a/lib/tasks/images.rake
+++ b/lib/tasks/images.rake
@@ -43,7 +43,7 @@ task "images:clean_orphans" => :environment do
     Upload.joins("LEFT OUTER JOIN post_uploads ON uploads.id = post_uploads.upload_id")
           .where("post_uploads.upload_id IS NULL")
           .find_each do |u|
-      u.delete
+      u.destroy
       putc "."
     end
   end