Will My 1099 Income Be Reported To My State Income Tax/unemployment?

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It will ultimately show up probably as a 1099 misc. You will also receive, I believe a 1099G from your state, so when you do your taxes the income could overlap and possibly throw up a red flag, however it won't really show actual dates worked, probably just a gross $ amount. There is also the issue of a W9 which you would fill out as an independent contractor or an employee which ties your social security number to all reportable income. There is also the possibility of a random audit conducted by your state to make sure UI compliance is in place.
Bottom line: Probably about a 50 50 chance you will eventually get caught. You have to weigh the risk. In the State of Indiana, where I live, there is a 20% rule, which basically says that any income you receive over 20% of your base is deducted from your benefits on a dollar for dollar basis. If your base is $300.00 you will still receive $ 60.00 no matter how much the income is for that week, and it is done on a week to week basis. There is also still the $25.00 kicker from the stimulus plan that comes from Federal. No easy answer for this one. Only sure way to avoid this is cash under the table. Whoops!!
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