If you have some un-filed returns, you will want to get back in the IRS system while creating the least amount of attention. Here is what you need to do:
4. When completing a tax organizer for un-filed returns, do not get overly aggressive with deductions you cannot clearly substantiate if you’re required to do so by the IRS. The last thing you need, in addition to being behind on filing, is for them to start auditing the returns you do file. If you’re like most taxpayers with un-filed returns, you probably don’t have the money to pay the amounts owed on the returns. You’ll likely be requesting some kind of deal with the IRS to pay less than the total amount owed. Knowing this, it makes no sense at all to file aggressive tax returns when you know you can’t pay what you owe. On the other hand, if you intend to write a check to the IRS for whatever you owe, then take every deduction allowed.
5. WARNING: If you have multiple year of un-filed tax returns, try to prepare one year at a time. Do not try to gather all the information for all the year at the same time. In most cases it’s too stressful to try to locate all of the information at one time. Break the project up into one year at a time.
6. File each tax return by mail. Do not include more than one tax return per envelope. If you have multiple returns prepared at the same time….mail one every couple of days. This avoids one IRS employee having all of your returns show up on their desk on one day, which may cause some curiosity or suspicion.
7. The IRS will send you a letter (read that “bill”) for each tax return you file. Don’t be alarmed…that’s supposed to happen. Wait until you receive all of them before deciding what course of action you’re going to take. If you start dealing with each letter (bill) independently, you’ll confuse yourself….and the IRS. Only proceed to the next step after you have received all the letters (bills).