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I have been having problems with this myself a way that worked for me was to release the Powder Ganger prisoners in the quest Booted for two loyalty points then to kill Silus during the interview process at Camp McCarran for one loyalty point for the other two i saved the NCR prisoners in the quest Back In Your Own Backyard i hope this helps.

If worst comes to worst take him with you to the fort and kill Caesar. Not the easiest thing, but he'll appreciate it.

See I Did kill Silus and ceaser Killed the NCR Cor Facility so couldnt do booted i have the guide so i know what to do but it doesnt cover this situation but thanks anyway

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