Why does the auto-update not work?

Oct 18, 2011
I have a Moto Droid original. When I try to "update now" (using the auto-downloaded update packages), the phone reboots to the clockword mod recovery menu, from which I appear to be unable to apply the MIUI update. (There is an option to apply the update.zip, but that's an old cyanogen update.zip that I applied several months ago, and using just reflashes w/ cyan.)