After seeing some of the problems that Microsoft has had upgrading people from Internet Explorer 6 and also seeing how Firefox has automatic updates, it's made me consider the benefits and drawbacks of a push-style upgrade system for our web app. In your opinion, should a web app have automatic updates? Why or why not? If yes, what are some of the issues that need to be taken into consideration and what strategies would you employ to make the upgrades as seamless as possible? Are there any existing examples you could point to of web apps that have a similar system?
Edit: For clarification, the web app is a content management system with a website front-end, similar to Joomla or Drupal. We would be offering the CMS as a product, so any updates would install the latest version of the application on our clients' servers.