My friend files for extension nearly every where because he is an idiot and has not been audited.

I always file mid Feb. and I have been audited twice now. No flags, just random picks.

It's a pain in the ass but I have learned to just keep ALL my files sorted and neat and to maintain it throughout the year instead of a panic crunch time when the IRS comes knocking.

I think you get an automatic extension until June if you're out of the country.

Many taxpayers extend. It's definitely not a red flag. One thing to understand is that the money is still due on 4/18 (if you will owe money). The extension is for the time to file not the time to pay.

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Many taxpayers extend. It's definitely not a red flag. One thing to understand is that the money is still due on 4/18 (if you will owe money). The extension is for the time to file not the time to pay.

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Definitely agree.

I've done it a few times. Never been audited. Same for all my friends.

There are other things that you'll be flagged for, but I don't believe this is one of them.

Lots of people file extensions these days due to late K1 arrivals.

I would talk with your guy and give him an estimate of where you think you'll end up. At the very least he could compare what you've paid in (that's usually easy to get) against your prior year income and make sure it's close.

I file late almost every year. I also pay a fair amount in taxes and always owe. They are more than willing to take a check, anytime. If you're expecting a refund, you're extending the term of your interest free loan.

I have been a contractor for the last 7 years, filed extensions every year without problems. My dad was a dentist that did a lot of cash business and filed extensions for as long as I can remember, probably the duration of his 30yr practice and was never audited.