Received Est. Tax Form 1040-ES For First Time

[Zele]

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OP stated he was now "playing as sole source of income" and asked about "gambler" filings. I'm betting he will get the pleasure of paying SE tax which will probably put him over 20%.

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That's part of my point. No one has really tested whether the IRS can make you file as a professional gambler, even if it is your sole source of income. They probably can, but nobody really knows yet.

[permafrost]

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Alright, so if I cashed in the main event, I have to make a payment by Friday, using 1040-ES? My grandfather is a tax preparer so it's not that big a problem, but I want to make sure I do owe the money now rather than April 15th. And could I pay it in installments, one now, one later this year?

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Whether you need to make an estimated payment Friday depends on your 2005 tax, your estimated 2006 tax, withholdings paid from employment, etc. If you have to do estimated, with few exceptions the highest required total of payment and withholding is the same as your 2005 tax. You pay any balance when filing.

If you do have to pay an est. payment for your big win, you should pay all now. Call your grandfather soon for his advice. My advice is guaranteed to be mine.