diff --git a/app/models/message.rb b/app/models/message.rb
index c6fe1dc85..205785414 100644
--- a/app/models/message.rb
+++ b/app/models/message.rb
@@ -51,6 +51,8 @@ class Message < ActiveRecord::Base
                             :author_key => :author_id
   acts_as_watchable
 
+  attr_writer :deleted_attachment_ids
+
   validates_presence_of :board, :subject, :content
   validates_length_of :subject, :maximum => 255
   validate :cannot_reply_to_locked_topic, :on => :create
@@ -58,6 +60,7 @@ class Message < ActiveRecord::Base
   after_create :add_author_as_watcher, :reset_counters!
   after_update :update_messages_board
   after_destroy :reset_counters!
+  after_save :delete_selected_attachments
   after_create_commit :send_notification
 
   scope :visible, (lambda do |*args|
@@ -73,6 +76,14 @@ class Message < ActiveRecord::Base
         user.allowed_to?(:edit_messages, message.project)
       end
   )
+  safe_attributes(
+    'deleted_attachment_ids',
+    :if =>
+      lambda do |message, user|
+        message.attachments_deletable?(user)
+      end
+  )
+
   def visible?(user=User.current)
     !user.nil? && user.allowed_to?(:view_messages, project)
   end
@@ -121,12 +132,23 @@ class Message < ActiveRecord::Base
     project.notified_users.reject {|user| !visible?(user)}
   end
 
+  def deleted_attachment_ids
+    Array(@deleted_attachment_ids).map(&:to_i)
+  end
+
   private
 
   def add_author_as_watcher
     Watcher.create(:watchable => self.root, :user => author)
   end
 
+  def delete_selected_attachments
+    if deleted_attachment_ids.present?
+      objects = attachments.where(:id => deleted_attachment_ids)
+      attachments.delete(objects)
+    end
+  end
+
   def send_notification
     if Setting.notified_events.include?('message_posted')
       Mailer.deliver_message_posted(self)
diff --git a/app/views/messages/_form.html.erb b/app/views/messages/_form.html.erb
index e030627a2..5bd56c67c 100644
--- a/app/views/messages/_form.html.erb
+++ b/app/views/messages/_form.html.erb
@@ -32,6 +32,27 @@
 <%= wikitoolbar_for 'message_content', preview_board_message_path(:board_id => @board, :id => @message) %>
 <!--[eoform:message]-->
 
-<p><%= l(:label_attachment_plural) %><br />
-<%= render :partial => 'attachments/form', :locals => {:container => @message} %></p>
+<fieldset>
+  <legend><%= l(:label_attachment_plural) %></legend>
+<% if @message.attachments.any? && @message.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 @message.deleted_attachment_ids.blank? %>">
+  <% @message.attachments.each do |attachment| -%>
+    <span class="existing-attachment">
+      <%= text_field_tag nil, attachment.filename, :id => nil, :class => 'filename', :disabled => true %>
+      <label>
+        <%= check_box_tag 'message[deleted_attachment_ids][]',
+                          attachment.id,
+                          @message.deleted_attachment_ids.include?(attachment.id),
+                          :id => nil, :class => 'deleted_attachment' %> <%= l(:button_delete) %>
+      </label>
+    </span>
+  <% end -%>
+    <hr />
+  </div>
+<% end -%>
+  <div id="new-attachments" style="display:inline-block;">
+    <%= render :partial => 'attachments/form', :locals => {:container => @message} %>
+  </div>
+</fieldset>
 </div>
diff --git a/test/functional/messages_controller_test.rb b/test/functional/messages_controller_test.rb
index b42c891a5..0105cb4fb 100644
--- a/test/functional/messages_controller_test.rb
+++ b/test/functional/messages_controller_test.rb
@@ -21,7 +21,7 @@ require File.expand_path('../../test_helper', __FILE__)
 
 class MessagesControllerTest < Redmine::ControllerTest
   fixtures :projects, :users, :email_addresses, :user_preferences, :members, :member_roles, :roles, :boards, :messages, :enabled_modules,
-           :watchers
+           :watchers, :attachments
 
   def setup
     User.current = nil
@@ -235,6 +235,29 @@ class MessagesControllerTest < Redmine::ControllerTest
     assert_equal Board.find(2), message.board
   end
 
+  def test_post_edit_with_deleted_attachment_ids
+    set_tmp_attachments_directory
+    @request.session[:user_id] = 2
+    message = Message.find(1)
+    attachment = message.attachments.first
+    assert_difference 'Attachment.count', -1 do
+      post(
+        :edit,
+        :params => {
+          :board_id => 1,
+          :id => 1,
+          :message => {
+            :subject => 'New subject',
+            :content => 'New body',
+            :deleted_attachment_ids => [attachment.id]
+          }
+        }
+      )
+    end
+    message.reload
+    assert_not_includes message.attachments, attachment
+  end
+
   def test_reply
     @request.session[:user_id] = 2
     post(