Probably a bios setting to tell the hardware which/both display to use.
Unless the dock/replicator is interfering.
Generally once a x starts it loads higher level 'drivers' and takes control of the hardware.
Maybe the KMS is doing similar in debian, even without the bios setting.
What video hardware and drivers are you using?
I have a lappy with a busted screen and an external monitor (VGA-out on the laptop itself), with the bios set to 'both'.
All the POST and boot messages as well as 'real-mode' DOS and non-x linux shows on both (well it used to, and still would if it wasn't stuffed) but once X or windows starts the video driver takes over and displays as per the software settings.
This was problematic on windows as I had to turn on the second monitor using the GUI
. Luckily I remembered VNC was already installed
, although I haven't bothered booting win on it in over a year now...