Someone on BSN was awesome and tracked the flags down so let's get hacking!
(I'm also gonna guess it's because the vast majority of players leave poor Kaidan on Virmire _ ) However, said Bioware guy mentioned that if you could set the Ashley plot flag to 8, it would probably fix the problem. Someone from Bioware posted about the bug but said that it's probably not going to get fixed because it might wreck something else. Or if you get Ashley back really late into the game (or if you're mean to her) then you might not see all of it. Basically, if you've got Kaidan in your savegame you're never going to see Ken and Gabby's dialogue. Somewhere along the line in ME3's development, the plot flag that controls engineering banter got switched to the 'are you pals with Ashley' flag. Unofficially, however, there's a solution! A solution with hacking. If you've ever played through ME3 and wondered why Gabby and Ken were so quiet, it's due to a bug that probably won't get fixed officially.