To keep it short: When I tried to make Oberland Station a vassal settlement, one defender was on their way to Back Street Apparel as they were in the process of being kidnapped. By the time I reached that settler and down her, the downed defenders at Oberland were back up and killing the raiders. The raiders could not down the citizens and the raid failed. A few notes: The kidnapped defender was classified as a settler and not a citizen, but were downed just like citizens. In other words, I could not kill this kidnapped settler. Also the kidnapped settler was not hostile, but also could not be communicated with. I attempted to tag and run with the settler to get her to follow me back to Oberland, but the citizens healed up and killed the raiders by the time I got to a quarter of the way there. Instead of fast travel I pursued on foot before they could reach Back Street Apparel. By the time I reached and subdued her, the citizens had already started to kill my raiders.