What do you guys think is best practice regarding auto-updating? Google Chrome for instance seems to auto-update itself as soon as it get's a chance without asking and I'm fine with it. I think most "normal" users benefits from updates being a transparent process.

Then again, some more technical users might be miffed if you update their app without permission, as I see it there's 3 options:

1) Have a checkbox when installing that says "allow automatic updates"

2) Just have a preference somewhere that allows you to "disable automatic updates" so that you have to "check for updates manually"

I'm leaning towards 2) because 1) feels like it might alienate non-technical users and I'd rather avoid installation queries if possible. Also I'm thinking about making it easy to downgrade if an upgrade (heaven forbid) causes trouble, what are your thoughts?

Another question, even if auto-updates are automatically, perhaps they should be announced. If there's new features for example otherwise you might not realize and use them

One thing that kinda scares me though is the security implications, someone could theorically hack my server and push out spyware/zombieware to all my customers. It seems that using digital signatures to prevent man-in-the-middle attacks is the least you could do otherwise you might be hooked up to a network that spoofs the address of of update server.