According to the TNG episode "The Defector", the Norkan Outposts were destroyed in a massacre by the Romulans.
Now I admit to knowing very little about stardates and the entire TOS series timelines, but my questions are these:
Did the Norkan Outposts belong to the Federation?
And if so...
When was the Federation formally at war with the Romulan Star Empire?
Please forgive my ignorance on this matter.