I got a Nokia n800 Internet tablet a few months ago and installed the Maemo os2008 software platform. I put the n800 in red pill mode to install some packages, and I just left it that way and forgot all about red/blue pill mode.
It didn't take long for me to find that updates just didn't work, but I never put the two things (red pill mode and broken updates) together. Looks like this is a well-known problem (see the bottom of the red pill mode wiki page linked above).
So if you put your n800 in red pill mode and updates don't work (mine complained that it needed to resolve libglade dependencies: it seemed to want to update to a version which was already installed), put it back in blue pill mode and try running updates. That worked for me.