Carry-forward of individual losses, with late-filed past taxes [US]
The 2012 return was due 4/15/2013 (I'm assuming it didn't fall on a weekend). No late filing penalty if there was no tax due, but he has until 4/15/2016 to file for a refund or to document anything that should have carried forward. Is Jim right to be worries? Yes, since the statute of limitations for refunds for 2012 is close and he might lose any tax refunds he might be entitled to for that year. Also, the pattern itself may raise some flags of suspicion and trigger audits, both because of such a variance in income and because of the medical expenses (which are generally considered a red flag). So he might get audited. However, if all the income and expenses are properly documented, audit itself should not be a problem.
"This is ridiculous. Of course some companies don't pay taxes each year. Off the top of my head, NOL's (net operating losses) can be carried forward 20 years and will definitely reduce tax liability. For that matter, a loss during any year prevents paying income tax (though sales, property, ad valorem and other taxes may apply). Other companies may get capital credits, green credits, or other subsidies that might prevent a tax liability. None of these indicate that a corporation is getting away with anything. The IRS is a lot better at its job than most people think.  The point is, you can't look at any individual year and make an accurate assessment of a company's (or even an individual's) tax burden. It's completely dishonest reporting.  Source: I'm a state tax auditor, and my job is to make sure corporations pay what they are supposed to.  EDIT: additionally, 2010 was the heart of the recession for a lot of companies. There were a LOT of corporations that took losses that year. So to say that ""GE took in 14.2 billion and paid no taxes"" is misleading: you have to say WHY they paid no taxes or you're just blowing hot air. Taxes are assessed on **income**, not **revenue**. There is a big difference." Generally speaking, each year, mutual funds distribute to their shareholders the dividends that are earned by the stocks that they hold and also the net capital gains that they make when they sell stocks that they hold. If they did not do so, the money would be income to the fund and the fund would have to pay taxes on the amount not distributed.  (On the other hand, net capital losses are held by the fund and carried forward  to later years to offset future capital gains).  You pay taxes on the amounts of the distributions declared by the fund. Whether the fund sold a particular stock for a loss or a gain (and if so, how much) is not the issue; what the fund declares as its distribution is. This is why it is not a good idea to buy a mutual fund just before it makes a distribution; your share price drops by the per-share amount of the distribution, and you have to pay taxes on the distribution. If you didn't receive the money in 2012 or have constructive receipt you really can't claim the income. If the company is going to give you a 1099 for the work they aren't going to give you one until next year and if you claim it this year you will have a hard time explaining the income difference. On the other hand if this isn't miscellaneous income, but rather self employment income and expenses you should be able to claim the expenses in 2012 and if you have a loss that would carry over to 2013. Note it is possible to use an accrual basis if you are running a business (which would allow you to do this), but it is more complex than the cash accounting individual tax payers use. Yes, you can send in a 2012 1040-ES form with a check to cover your tax liability. However, you will likely have to pay penalties for not paying tax in timely fashion as well as interest on the late payment. You can have the IRS figure the penalty and bill you for it, or you can complete Form 2210 (on which these  matters are figured out) yourself and file it with your Form 1040. The long version of Form 2210 often results in the smallest extra amount due but is considerably more time-consuming to complete correctly. Alternatively, if you or your wife have one or more paychecks coming before the end of 2012, it might be possible to file a new W-4 form with the HR Department with a request to withhold additional amounts as Federal income tax. I say might because if the last paycheck of the year will be issued in just a few days' time, it might already have been sent for processing, and HR might tell you it is too late. But, depending on the take-home pay, it might be possible to have the entire $2000 withheld as additional income tax instead of sending in a 1040-ES. The advantage of doing it through withholding is that you are allowed to treat the entire withholding for 2012 as satisfying the timely filing requirements. So, no penalty for late payment even though you had a much bigger chunk withheld in December, and no interest due either.  If you do use this approach, remember that Form W-4 applies until it is replaced with another, and so  HR will continue to withhold the extra amount on your January paychecks as well.  So, file a new W-4 in January to get back to normal withholding. (Fix the extra exemption too so the problem does not recur in 2013). The IRS allows filers to attach a statement explaining the reason for late filing.  I have had clients do this in the past, and there has never been an issue (not that that guarantees anything, but is still good to know). Generally, the IRS is much more lenient when a taxpayer voluntarily complies with a filing requirement, even if it's late, than if they figure it out themselves and send a notice. If you withdraw your funds from your 401k and DO NOT mive it into another 401k plan or IRA within 60 days it will constitute as an early distribution which will carry a panlty of 10% as well as have income tax owed on it. Your question begins with a misunderstanding.  When you prepare your tax return (Form 1040/1040A/1040EZ) you always try to minimize your total tax bill.  When you fill out form W4 you trying to estimate how much tax will be shown on next years tax return.  The penalty for having too much tax withheld is not having the use of the money until you get a tax refund. At the moment interest rates are very low and your economic loss is the temporary loss of access to the money. One exception would be if you are carrying credit card debt. In that case you are, in effect, paying 20-30% interest to borrow money you lending to the US Treasury for 0% interest. The penalty for having too little tax withheld is having to make a large payment with your tax return. If your pre-payments aren't at least as much as your total income tax from last year there may also be modest underpayment penalty based on the difference between your pre-payments and your total income tax from last year or this year whichever is less. A large underpayment will trigger a different larger underpayemnt penalty. The W4 combined with the withholding rates tends to over-withhold income tax for most, but not all, taxpayers. Most people don't have enough savings to pay a large tax due, which leads to more penalties and an even larger bill. Over-witholding protects the overall tax system from the consequences of those events. People tend to be very unhappy, not quietly. On balance your greatest economic benefit depends on whether or not you have high interest debt. If you do, then accurate and even slightly under-withholding will probably work to your advantage as long as you can pay next 4/15. If not, avoiding the chance of having any unexpected balance due next year may be more important. No.  You already received the deduction, since that lost FSA money was pre-tax.  You can't double dip.  However if your FSA amount was less than your actual expenses, you can file on the difference. Example: $4500 actual expenses, $3000 FSA (lost).  You can get the dependent care credit based on $1500.