What tax year does my income get assigned to if my client sends the payment in December but I receive it in January?
Confused? see your CPA
"As long as you paid 100% of your last year's tax liability (overall tax liability, the total tax to pay on your 1040) or 90% of the total tax liability this year, or your underpayment is no more than $1000, you won't be penalized as long as you pay the difference by April 15th. That's per the IRS. I don't know where the ""10% of my income"" came from, I'm not aware of any such rule." Form 1099-misc reports PAYMENTS, not earnings.  This does not imply the EARNINGS are not taxable in the year they were earned. If you're paying a foreign person directly - you submit form 1042 and you withhold the default (30%) amount unless the person gives you a W8 with a valid treaty claim and tax id. If so - you withhold based on the treaty rate. From the IRS: General Rule In general, a person that makes a payment of U.S. source income to a   foreign person must withhold the proper amount of tax, report the   payment on Form 1042-S and file a Form 1042 by March 15 of the year   following the payment(s). I'd suggest to clarify this with a licensed tax adviser (EA/CPA licensed in your State) who's familiar with this kind of issues, and not rely on free advice on the Internet or DIY. Specific cases require specific advice and while the general rule above holds in most cases - in some there are exceptions. Why would the IRS be coming after you if you reported the income? If you reported everything, then the IRS will use the 1099 to cross-check, see that everything is in order, be happy and done with it. The lady was supposed to give you the 1099 by the end of January, and she may be penalized by the IRS for being late, but as long as you/wifey reported all the income - you're fine. It was supposed to be reported on Schedule C or as miscellaneous income on line 21 (schedule C sounds more suitable as it seems that your wifey is in a cleaning business). But there's no difference in how you report whether you got 1099 or not, so if you reported - you should be fine. Many of the custodians (ie. Schwab) file for an extension on 1099s.  They file for an extension as many of their accounts have positions with foreign income which creates tax reporting issues.  If they did not file for extension they would have to send out 1099s at the end of January and then send out corrected forms.  Obviously sending out one 1099 is cheaper and less confusing to all.  Hope that helps, Well, consult with a CPA, but I guess you don't have to pay taxes on 2012 with a correct accounting system since this is the money you are going to completely earn within 2013 so you can record it as future earning which is called deferred revenue or advance payments or unearned revenue. I remember reading in an earlier version of Pub 590 (or possibly the Instructions for Form 8606) that timely contributions for Year X to an IRA are deemed to have been made on January 1 of Year X regardless of when they were actually made, but I don't seem to be able to find it now in current versions of Pubs 590a or 590b and so cannot include a citation of chapter and verse. Be that as it may, the calculations on on Form 8606 Part I effectively track basis on an annual basis rather than on a daily basis, and so the fact that the Traditional IRA has a zero balance (and basis 0 too) at some time during the year doesn't matter in the least.  In detail (though you didn't ask for it) Note that the whole $6500 that you put in remains non-deductible in its entirety, but you owe taxes on only $93,900 of that $100K that you rolled over into a Roth IRA and not on the whole $100K as you were assuming would have been the case. So, in effect, of that $6500 nondeductible contribution to your Traditional IRA, you did really get to deduct $6100 from your taxable income for 2016, and make only a $400 nondeductible contribution, exactly equal to your basis in your Traditional IRA as per the Form 8606 calculations.  I can only assume that the software package that you are using reproduces the above calculations exactly and does what the IRS says you must do on Form 8606 rather than what you get by tracking the basis on a daily basis. IRS regulations and instructions are not necessarily the same as what the tax law says; they are interpretations of the tax law based on what the IRS understands the tax law to say. People have challenged various specific IRS regulations and interpretations as being different from what the law says in Tax Court and been successful in some cases and failed in others. If you believe that tracking basis on a daily basis is what the law says (instead of just being reasonable and rational: reasonableness and rationality are not required either of Congress in the laws that they write or the IRS regulations that interpret the laws), you should take up the matter with the IRS or the Tax Court. IRS pub 521 has all the information you need. Expenses reimbursed. If you are reimbursed for your expenses and you   use the cash method of accounting, you can deduct your expenses either   in the year you paid them or in the year you received the   reimbursement. If you use the cash method of accounting, you can   choose to deduct the expenses in the year you are reimbursed even   though you paid the expenses in a different year. See Choosing when to   deduct, next. If you deduct your expenses and you receive the   reimbursement in a later year, you must include the reimbursement in   your income on Form 1040, line 21 This is not unusual. Anybody who moves near the end of the year can have this problem. The 39 week time test also can be an issue that span over 2 tax years. I would take the deduction for the expenses as soon a I could, and then count the income in the later year if they pay me back. IF they do so before April 15th, then I would put them on the same tax form to make things easier. Not correct. First - when you say they don't tax the reimbursement, they are classifying it in a way that makes it taxable to you (just not withholding tax at that time).  In effect, they are under-withholding, if these reimbursement are high enough, you'll have not just a tax bill, but penalties for not paying enough all year.  My reimbursements do not produce any kind of pay stub, they are a direct deposit, and are not added to my income, not as they occur, nor at year end on W2.  Have you asked them why they handle it this way? It's wrong, and it's costing you. "We will bill our clients periodically and will get paid monthly. Who are ""we""? If you're not employed - you're not the one doing the work or billing the client. Would IRS care about this or this should be something written in the   policy of our company. For example: ""Every two months profits get   divided 50/50"" They won't. S-Corp is a pass-through entity. We plan to use Schedule K when filing taxes for 2015. I've never filled a schedule K before, will the profit distributions be reflected on this form? Yes, that is what it is for. We might need extra help in 2015, so we plan to hire an additional   employee (who will not be a shareholder). Will our tax liability go   down by doing this? Down in what sense? Payroll is deductible, if that's what you mean.  Are there certain other things that should be kept in mind to reduce the tax liability? Yes. Getting a proper tax adviser (EA/CPA licensed in your State) to explain to you what S-Corp is, how it works, how payroll works, how owner-shareholder is taxed etc etc." I think you should consult a professional with experience in 83(b) election and dealing with the problems associated with that. The cost of the mistake can be huge, and you better make sure everything is done properly. For starters, I would look at the copy of the letter you sent to verify that you didn't write the year wrong. I know you checked it twice, but check again. Tax advisers can call a dedicated IRS help line for practitioners where someone may be able to provide more information (with your power of attorney on file), and they can also request the copy of the original letter you've sent to verify it is correct. In any case, you must attach the copy of the letter you sent to your 2014 tax return (as this is a requirement for the election to be valid). "Your question does not say this explicitly, but I assume that you were once a W-2 employee.  Each paycheck a certain amount was withheld from your check to pay income, social security, and medicare taxes.  Just because you did not receive that amount of money earned does not mean it was immediately sent to the IRS.  While I am not all that savvy on payroll procedures, I recall an article that indicated some companies only send in withheld taxes every quarter, much like you are doing now.  They get a short term interest free loan.  For example taxes withheld by a w-2 employee in the later months of the year may not be provided to the IRS until 15 January of the next year.   You are correct in assuming that if you make 100K as a W-2 you will probably pay less in taxes than someone who is 100K self employed with 5K in expenses.  However there are many factors.  Provided you properly fill out a 1040ES, and pay the correct amount of quarterly payments, you will almost never owe taxes.  In fact my experience has been the forms will probably allow you to receive a refund.  Tax laws can change and one thing the form did not include last year was the .9% Medicare surcharge for high income earners catching some by surprise.    As far as what you pay into is indicative of the games the politicians play.  It all just goes into a big old bucket of money, and more is spent by congress than what is in the bucket.  The notion of a ""social security lockbox"" is pure politics/fantasy as well as the notion of medicare and social security taxes.  The latter were created to make the actual income tax rate more palatable.     I'd recommend getting your taxes done as early as possible come 1 January 2017.  While you may not have all the needed info, you could firm up an estimate by 15 Jan and modify the amount for your last estimated payment.  Complete the taxes when all stuff comes in and even if you owe an amount you have time to save for anything additional.  Keep in mind, between 1 Jan 17 and 15 Apr 17 you will earn and presumably save money to use towards taxes.  You can always ""rob"" from that money to pay any owed tax for 2016 and make it up later. All that is to say you will be golden because you are showing concern and planning.  When you hear horror stories of IRS dealings it is most often that people spent the money that should have been sent to the IRS." This is a common occurrence, I know people who moved and then only remember the next spring during tax season that they never filed a new state version of a W-4. Which means for 3 or 4 months in the new year money is sent to the wrong state capital, and way too much was sent the previous year. In the spring of 2016 you should have filed a non-resident tax form with Michigan. On that form you would specify your total income numbers, your Michigan income numbers, and your other-state income numbers; with Michigan + other equal to total. That should have resulted in getting all the state taxes that were sent to Michigan returned.  It is possible that the online software is unable to complete the non-resident tax form. Not all forms and situations can be addressed by the software. So you may need to fill out paper forms. You should be able to find what you need on the state of Michigan website for 2015 Taxes. A quick read shows that you will probably need the Michigan 1040, schedule 1 and Schedule NR You may run into an issue if your license, car registration, voter registration, and other documentation point to you being a resident for the part of the year you earned that income. That means you will have to submit Form 3799 Statement to Determine State of Domicile You want to do this soon because there are deadlines that limit how far back you can files taxes. The state may also get tax information from the IRS and could decide that all your income from 2015 should have applied to them, so they will be sending you a tax bill plus penalties for failure to file. In the United States the general policy is that the IRS would consider it income when you have access to the money. I work for a company that has a contract with another company. Near the end of the year I turn in a time card that has my hours that I worked as of that date. Because they don't pay me until early January the money on the check is counted in the new year. I couldn't touch the money until they issued the check. If they had paid me on December 31st it would have counted as the old year, even if I only had a short window to have access to it before the year ended. It would even count as old year money if I held on to the December check, but didn't deposit it until March. So it would become income when you could use it. So If you could access it via a check, or debit card, or transfer it to the bank it is now income. Of course that is in the United States. You would need to see what the situation is in Singapore.... The edge cases always depend on the country. I will answer this question broadly for various jurisdictions, and also specifically for the US, given the OP's tax home: Generally, for any tax jurisdiction If your tax system relies on periodic prepayments through the year, and a final top-up/refund at the end of the year (ie: basically every country), you have 3 theoretical goals with how much you pre-pay: Specifically, for the U.S. All information gathered from here: https://www.irs.gov/businesses/small-businesses-self-employed/estimated-taxes. In short, depending on your circumstance, you may need to pay quarterly estimated tax payments to avoid penalties on April 15th. Even if you won't be penalized, you, may benefit from doing so anyway (to force yourself to save the money necessary by April 15th).  I have translated the general goals above, into US-specific advice: