Ok, so I've got the OG Droid and I rooted a while back using Soup or Root v2.06 Beta and everything worked smoothly. I never installed clockworkmod recovery then or flashed any roms, just rooted at the time to be able to use some apps that required root. Well, I recently noticed that some of these apps weren't working correctly, so I went into my Superuser app and clicked to check for updates on the binary (currently is v2.3.1-ef). A popup would come up that said "checking..." then would disappear and nothing would happen. So i went to the marketplace and updated the Superuser app... (ChainsDD now v184.108.40.206). So then I again tried clicking to update the binary.
Now it comes up with a pop-up that says "New version of su - There is a new version of the su binary available. Press OK to attempt to install it automatically." OK so I click "ok" and it says: "An error occurred and su was not updated. A zip file (su-2.3.1-bin-signed.zip) has been placed on your sdcard, please reboot into recovery mode and flash it to update your su binary.
Well reboot into recovery mode and it goes into "Android system recovery <3e>" with these options
-reboot system now
-wipe data/factory reset
-wipe cache partition
-wibe baseband data
Ok so I tried apply sdcard:update.zip which I know is not flashing the su zip file on my SD card, and obviously that doesnt work. So, reboot and download clockworkmod Rom Manager. When I click on "Flash Clockworkmod Recovery" I get confirm phone model (Motorola Droid - CDMA), then it downloads a file and near the end of download I get the message "An error occurred while attempting to run privileged commands!" So, obviously my Superuser is not working at all. So, I need clockworkmod recovery to flash my new su binary, but i need superuser working to flash clockworkmod recovery. So i am stuck. Where do i go now?