I know this is an old thread.. But I am having the exact same issue.

The "Daily Status Reports" have stopped working on my win2008r2 server.

They stopped working quite some time ago.. Just like James, I have confirmed the administrators email address, the Send Daily Status Report option on the server config page is checked.

I am getting Update messages to the admin email, but am not getting the "Daily Status Reports" anymore.

Is there any new info about this problem?