diff --git a/app/controllers/documents_controller.rb b/app/controllers/documents_controller.rb
index 6facd7b14..ffd432fa1 100644
--- a/app/controllers/documents_controller.rb
+++ b/app/controllers/documents_controller.rb
@@ -75,7 +75,7 @@ class DocumentsController < ApplicationController
     @document.safe_attributes = params[:document]
     if @document.save
       flash[:notice] = l(:notice_successful_update)
-      redirect_to document_path(@document)
+      add_attachment
     else
       render :action => 'edit'
     end
diff --git a/app/models/document.rb b/app/models/document.rb
index 4f562fc70..49b4fbba8 100644
--- a/app/models/document.rb
+++ b/app/models/document.rb
@@ -31,9 +31,12 @@ class Document < ActiveRecord::Base
                 :url => Proc.new {|o| {:controller => 'documents', :action => 'show', :id => o.id}}
   acts_as_activity_provider :scope => preload(:project)
 
+  attr_writer :deleted_attachment_ids
+
   validates_presence_of :project, :title, :category
   validates_length_of :title, :maximum => 255
 
+  after_save :delete_selected_attachments
   after_create_commit :send_notification
 
   scope :visible, lambda {|*args|
@@ -42,6 +45,10 @@ class Document < ActiveRecord::Base
   }
 
   safe_attributes 'category_id', 'title', 'description', 'custom_fields', 'custom_field_values'
+  safe_attributes(
+    'deleted_attachment_ids',
+    :if => lambda {|document, user| document.attachments_deletable?(user)}
+  )
 
   def visible?(user=User.current)
     !user.nil? && user.allowed_to?(:view_documents, project)
@@ -66,8 +73,19 @@ class Document < ActiveRecord::Base
     project.notified_users.reject {|user| !visible?(user)}
   end
 
+  def deleted_attachment_ids
+    Array(@deleted_attachment_ids).map(&:to_i)
+  end
+
   private
 
+  def delete_selected_attachments
+    deleted_ids = deleted_attachment_ids
+    return if deleted_ids.blank?
+    objects = attachments.where(:id => deleted_ids)
+    attachments.delete(objects) if objects.exists?
+  end
+
   def send_notification
     if Setting.notified_events.include?('document_added')
       Mailer.deliver_document_added(self, User.current)
diff --git a/app/views/documents/_form.html.erb b/app/views/documents/_form.html.erb
index b8b8c8404..338ec328f 100644
--- a/app/views/documents/_form.html.erb
+++ b/app/views/documents/_form.html.erb
@@ -13,12 +13,30 @@
 <% @document.custom_field_values.each do |value| %>
   <p><%= custom_field_tag_with_label :document, value %></p>
 <% end %>
-</div>
 
 <%= wikitoolbar_for 'document_description' %>
 
-<% if @document.new_record? %>
-<div class="box tabular">
-<p><label><%=l(:label_attachment_plural)%></label><%= render :partial => 'attachments/form', :locals => {:container => @document} %></p>
+<fieldset>
+<legend><%=l(:label_attachment_plural)%></legend>
+<% if @document.attachments.any? && @document.safe_attribute?('deleted_attachment_ids') %>
+<div class="contextual"><%= link_to l(:label_edit_attachments), '#', :onclick => "$('#existing-attachments').toggle(); return false;" %></div>
+<div id="existing-attachments" style="<%= 'display:none;' if @document.deleted_attachment_ids.blank? %>">
+  <% @document.attachments.each do |attachment| %>
+  <span class="existing-attachment">
+    <%= text_field_tag '', attachment.filename, :class => "icon icon-attachment filename", :disabled => true %>
+    <label class='inline'>
+      <%= check_box_tag 'document[deleted_attachment_ids][]',
+                        attachment.id,
+                        @document.deleted_attachment_ids.include?(attachment.id),
+                        :id => nil, :class => "deleted_attachment" %>&nbsp;<%= l(:button_delete) %>
+    </label>
+  </span>
+  <% end %>
+  <hr />
 </div>
 <% end %>
+<div id="new-attachments" style="display:inline-block;">
+  <%= render :partial => 'attachments/form', :locals => {:container => @document} %>
+</div>
+</fieldset>
+</div>
diff --git a/test/functional/documents_controller_test.rb b/test/functional/documents_controller_test.rb
index 7470833d7..6b8b2b477 100644
--- a/test/functional/documents_controller_test.rb
+++ b/test/functional/documents_controller_test.rb
@@ -207,28 +207,76 @@ class DocumentsControllerTest < Redmine::ControllerTest
   end
 
   def test_update
+    set_tmp_attachments_directory
     @request.session[:user_id] = 2
-    put :update, :params => {
-        :id => 1,
-        :document => {
-          :title => 'test_update'
+    assert_difference 'Attachment.count' do
+      put :update, :params => {
+          :id => 1,
+          :document => {
+            :title => 'test_update'
+          },
+          :attachments => {
+            '1' => {'file' => uploaded_test_file('testfile.txt', 'text/plain')}
+          }
         }
-      }
+    end
     assert_redirected_to '/documents/1'
     document = Document.find(1)
     assert_equal 'test_update', document.title
   end
 
   def test_update_with_failure
+    set_tmp_attachments_directory
+    @request.session[:user_id] = 2
+    assert_no_difference 'Attachment.count' do
+      put :update, :params => {
+          :id => 1,
+          :document => {
+            :title => ''
+          },
+          :attachments => {
+            '1' => {'file' => uploaded_test_file('testfile.txt', 'text/plain')}
+          }
+        }
+    end
+    assert_response :success
+    assert_select_error /title cannot be blank/i
+  end
+
+  def test_update_with_deleted_attachment_ids
+    set_tmp_attachments_directory
     @request.session[:user_id] = 2
-    put :update, :params => {
+    document = Document.find(1)
+    attachment = document.attachments.first
+    assert_difference 'Attachment.count', -1 do
+      put :update, :params => {
         :id => 1,
         :document => {
-          :title => ''
+          :title => 'test_update',
+          :deleted_attachment_ids => [attachment.id]
         }
       }
-    assert_response :success
-    assert_select_error /title cannot be blank/i
+    end
+    document.reload
+    refute_includes document.attachments, attachment
+  end
+
+  def test_update_with_deleted_attachment_ids_and_failure_should_preserve_selected_attachments
+    set_tmp_attachments_directory
+    @request.session[:user_id] = 2
+    document = Document.find(1)
+    attachment = document.attachments.first
+    assert_no_difference 'Attachment.count' do
+      put :update, :params => {
+        :id => 1,
+        :document => {
+          :title => '',
+          :deleted_attachment_ids => [attachment.id]
+        }
+      }
+    end
+    document.reload
+    assert_includes document.attachments, attachment
   end
 
   def test_destroy