Okay, I'm guessing the following:
- Your settings are set so that your screen saver kicks in first, with a password
- Then, you have the monitor set to sleep
- Then, you have the computer set to sleep automatically
Does this happen when you put it to sleep manually, or only when you let it sleep automatically?
If you only have this issue with auto sleep, try to set your screen to go to sleep time to be "Never." I think if this is the case, there have been some people who have said that if the screen falls asleep before the computer, it won't wake up -- even in Panther. Not everyone, but seemingly just some screens.