That means you don't have a usable recovery rom installed. I had this trouble on my HTC Magic after I had gone through a rooting process, what was strange was I could do a nandroid backup and one was there! Anyway, because I was running an S=ON mboard, any attempt to install over USB with flashboot failed because it checks the sig. You may want to install your recovery ROM of choice by copying to SD, then while in debug mode from your computer, do
adb shell
flash_image recovery /sdcard/your-recovery-image.img
Before doing any of this, verify this rom works with your phone first, using flashboot without attempting to flash the phone.
DT