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If he's definitely firing another shot into this pot, I checkraise him all in.

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That's my problem. I'm not sure that he's definitely firing another bullet. Like I said, he seems kinda of passive. Do I check/raise, bet and hopefully push, or just open-push?

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If he seems passive he's not biting on an open-push. If he's passive, what percentage of the time is he going to raise so you can 3-bet him all-in? I think ideally check-raising him would be the best line.