It's tax extension filing day. Are you ready?EXPAND
It's tax extension filing day. Are you ready?
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Five Pieces of Advice on IRS Extension Deadline Day

If you filed an extension with the IRS, the deadline for filing is Thursday. Perhaps not the nerve-wracking time that April 15 is for the majority of Americans, but no one likes paying taxes or having to fill out paperwork that is so complicated only a CPA and Pythagorus can figure it out. But if you're filing on the deadline, here are a few pieces of advice from someone who has had to deal with the IRS on more than one occasion in his life.

File Even if You Can't Pay

This seems counterintuitive, like guessing on a question you don't know on the SAT, but it is important. The IRS loves paperwork. If it doesn't have a return on file, even if you owe ZERO dollars, it can penalize you. And the agency won't tell you it doesn't have it. You find out when, years later, you have to talk to an agent about something else and he says, ever so innocuously, "By the way, we don't have a tax return for you from 2012." You, shocked, say you will send one right away. A couple of months later, you get a notice saying you owe $172,127,561.10 for penalties and interest on that zero-dollar filing. Moral of the story: File first and worry about settling up later.

Require a Signature for All Mail You Send

Keep in mind that when you send a return through the mail — something many have to do because their return is too complicated for electronic filing — it's being sent to a government agency BY a government agency. That means there is no guarantee it will get there. I've had three business returns not filed because the IRS supposedly never got them. Fortunately, I sent them certified mail and required a signature card be signed and returned to me — FedEx or USPS overnight works too for tracking purposes. When I was told the IRS had never got them, I yelled "Ah ha!" as I jumped up and down and waved that beautiful green card in their faces...Okay, I was on the phone and instead of "Ah ha!" it was, "Oh, I have a return receipt I can show you," but you get the idea.

Ask for Help

And that reminds me, ask for help when needed. If you can't afford to use an accountant, go to an IRS help center — they do exist, but you might need an appointment, so check online — or call them. Contrary to popular belief, IRS agents are not all black-suit-wearing spies with the Mark of the Beast tattooed on the backs of their necks. They don't carry weaponry, unless they have been trained in death by Bic pen, and they are mostly friendly, albeit sometimes a bit beleaguered, but who could blame them? They work for the IRS!

Be Prepared to Wait if You Have to Call

If you do need to make a call, get comfortable. The wait time just to get someone on the line is often 45 minutes to more than an hour. The music, as you might imagine, is not terribly pleasant either. It's like preparing you for bad news by making you sit in rush hour traffic, not a wonderful experience. Best bet is to settle in, put your phone on speaker, turn the volume down and do something else. But don't lose track of your phone. If the agent gets on the line and you aren't there, he or she will hang up and then, well, I'm pretty sure this is how insanity begins.

If You Do Call and the Person Isn't Helping, Hang Up and Call Back

Years ago, an accountant friend of mine gave me this advice, and it has been invaluable. Most agents are nice enough, but some, like all of us, are downright jerks. They are probably not going to help you. In fact, they may make it worse. Granted, the pain of sitting on hold for another hour might be more than one human being can bear, but it is preferable to getting someone on the phone who will only make your IRS problem worse. The good news is this is the exception rather than the rule, but keep it in your back pocket and you'll get out of this alive. Good luck.

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