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Message: [QUOTE="zachvac, post: 1015815, member: 26306"] This. Also technically when you declare income you have to include all wins by session and then deduct losses. Shouldn't matter in terms of what you pay but does on the forms. ie say these are your sessions: +10 -5 +5 +7 -2 +15 -3 +6 -15 +23 Bottom line you win 41 but you actually have to declare and pay taxes on 66 and you can deduct 25. But yeah you have to pay taxes on any winnings as you win them not as you cash them out. That said if you don't cash them out the government has no way of knowing it's there, just know that the irs doesn't take kindly to tax fraud. [/QUOTE]