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Tax.appeal.168
Tax.appeal.168, Tax Accountant
Category: Tax
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Experience:  3+ decades of varied tax industry exp. Tax Biz owner
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I have not filed personal income tax since 2009. The IRS has

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I have not filed personal income tax since 2009. The IRS has not yet contacted me about any back year. How do I go about catching this up? if I start filing past years now will it raise flags and have them come down on me all at once for 6 years worth of what I might owe and possibly trigger some kind of collection? Most years before that I did not owe. Am I better off getting them all done and sent in, and then based on the total, ask for a settlement?
Submitted: 2 years ago.
Category: Tax
Expert:  Robin D. replied 2 years ago.
Hello and thanks for trusting me to help you today. I am a tax adviser with over 20 years of experience.
You can send them all in one envelope. If you do owe you can request a settlement (an Offer In Compromise).
An offer in compromise allows you to settle your tax debt for less than the full amount you owe. Before the IRS can consider your offer, you must be current with all filing and payment requirements. So filing all returns would cover your filing requirement.
If the IRS thinks that you could not pay the full amount and it was doubtful they could get the full amount from you then an OIC would be acceptable.
You would want to request an Installment Arrangement first (after you know what the tax liability is). Then you could request an Offer In Compromise.
FREE EXTRA INFORMATION FOR YOU
The IRS has a prequalifier tool that you can use after you know the amount you owe:
http://irs.treasury.gov/oic_pre_qualifier/
Expert:  Tax.appeal.168 replied 2 years ago.
Welcome. Thank you for choosing us to assist you. My name is ***** ***** my goal is to help make your life, a little... less taxing
DIFFERENT EXPERT HERE.
I regularly work with individuals in your situation. I have a different take on your situation.
1) When sending in multiple years, it is NOT recommended that you send all the returns in the same envelope. Why? Because, usually the clerks do not take the time to look through the paperwork and separate the returns. SEE BELOW:
You should mail each amended return in a separate envelope. The IRS has a habit of stapling everything together on a paper return and only one of the amended returns would get recorded. Be on the safe side and use two envelopes.
REFERENCE SOURCE:
ttlc.intuit.com/questions/2228283-can-i-mail-two-different-1040x-together-in-the-same-envelope
Even though the example refers to an amended return, this applies with regular returns as well.
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If you owe, the best thing to do is to try for an installment agreement. In spite of what you hear and see on the television, an Offer In Compromise is very difficult to be approved for. For more information regarding installment agreements, refer to the following IRS webpage:
http://www.irs.gov/Individuals/Payment-Plans-Installment-Agreements
Let me know if you require further assistance with this matter.