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The hardest thing about Hard is capturing the bosses alive.
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Agreed. I tried to, but it was impossible! I played through on easy just to get all the bounties alive, for the 20,000 moolah.
If I remember right, I think Glitch posted a while ago saying it is possible to bounty Looten Duke alive on hard, just that its incredibly difficult. I tried, and in my experience it was impossible- The only way I found to keep shooting him with the zapfly before his stamina regenerates was to get him stuck in the environment (bit of a cheat, I know!

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At the bottom of the ramp going down to the water facility, there's a stone platform on pillars. I found that if you lead him to this area, run through the tall grass and jump on top of the platform, Looten Duke stands still and doesn't shoot you, so I could repeatedly zap him without him doing anything!
With Duke having full health and stamina, I did nothing but zap him as fast as I could, and still found that his health drops quicker than his stamina. Every time I tried, he died. Considering I was zapping him as fast as possible, doing minimum damage, I'd say it's pretty impossible!
Has anyone here actually managed to get him alive on hard difficulty? Maybe there's something better than the zapfly for dropping his stamina?