My requirement is that my Windows 8 laptop should be encrypted (whole system drive) and ask for password on boot, except when it is docked in a specific docking station. If docked, it should boot automatically, without requiring any user input (think wake-on-LAN or similar).
Logically, the most straightforward way to achieve this would be to store the password (encrypted with some laptop-hardware-specific key) on a USB drive that's kept plugged in the docking station, so that the encryption software can read it and boot automatically; or ask for password if the key is not found.
Is there an encryption software with which it would be possible? So far I've looked at TrueCrypt and BitLocker (only Googled, not actually tested since I don't have a separate system to play with), and neither appear to be able to do this.