Will depositing $10k+ checks each month raise red flags with the IRS?
You're getting confused between several different things. 10K - cash transactions over $10,000 are reported to FinCEN under BSA. This is to prevent money laundering. IRS - IRS wants to see your tax return with all your income reported there. They don't see your bank deposits unless they audit you. 1 and 2 are not related at all. Contractors regularly deposit checks like this; if the income is legitimate don't worry. Report it to the IRS as income whether or not the customer issues you a 1099. With deposits like this you should be making quarterly payments to the IRS for your projected income. I do not think banks have an obligation to report any deposits to the IRS, however, they probably have an obligation to report deposits exceeding certain threshold amounts to FinCEN. At least that's how it works in Canada, and we're known to model our Big Brother-style activities after our neighbour to the South. Your main concern seems to be to be accused of something called 'smurfing' or structuring. http://en.wikipedia.org/wiki/Structuring Depositing money amounts (cash or checks) under the 10k limit to circumvent the reporting requirement. People have been investigated for depositing under the limit, e.g. small business owners. If you're always above 10k you should be fine, as your deposits are reported and shouldn't raise IRS or FBI suspicions.
"I have a related issue, since I have some income which is large enough to matter and hard to predict. Start with a best guess. Check what tax bracket you were in last year and withhold that percentage of the expected non-withheld income. Adjust upward a bit, if desired, to reflect the fact that you're getting paid more at the new job. Adjust again, either up or down, to reflect whether you were over-withheld or under-withheld last year (whether the IRS owed you a refund or you had to send a check with your return). Repeat that process next year after next tax season, when you see how well your guess worked out. (You could try pre-calculating the entire tax return based on your expected income and then divide any underpayment into per-paycheck additional withholding... but I don't think it's worth the effort.) I don't worry about trying to get this exactly correct. I don't stress about lost interest if I've over-withheld a bit, and as long as your withholding was reasonably close and you have the cash float available to send them a check for the rest when it comes due, the IRS generally doesn't grumble if your withholding was a bit low.  (It would be really nice if the IRS paid us interest on over-withholding, to mirror the fact that they charge us interest if we're late in returning our forms. Oh well.) Despite all the stories, the IRS really is fairly reasonable; if you aren't deliberately trying to get away with something, the process is annoying but shouldn't be scary. The one time they mail-audited me, it was several thousand dollars in my favor; I'd forgotten to claim some investment losses, and their computers noticed the error. Though I still say the motto of the next revolution will be ""No taxation without proper instructions!""" If the check was payable to you, you had 60 days to deposit to an IRA.  But, it needs to go into the same type of IRA as the 401(k) was. i.e. if the 401(k) was traditional, it goes into a traditional IRA, If 401(k) Roth, it goes into a Roth.  The 20% is not the penalty. The penalty is 10% for early withdrawal. The 20% is the tax withholding. If the 401(k) had $1250, and they kept $250 for taxes, you'd want to deposit the full $1250 into the IRA. At tax time, you'll get the $250 credited to your taxes, and either owe less or get a higher refund. You're asking three different questions...  Q1: What's to stop people not reporting income earned in this manner?  A: Nothing. Absolutely nothing. The IRS doesn't have the means to keep track of your cash flow and your reported taxes on the fly.  Q2: How could the IRS possibly keep track of that? A: When you get audited. If it ever did come up that things didn't balance you would end up owing back taxes, with interest and possibly fines.  Q3: Moral obligations aside... why report? A: Since you've dismissed 'doing your duty as a citizen' as a moral obligation, the only other real one is that it's a pain in the butt to get audited and it is expensive if you lie and get caught. Aside from the fact that probably nobody is ever going to come and ask for that proof unless your amounts get five digits (or you're unlucky), if you never before reimbursed yourself, your old tax declarations would clearly show that. You can't prove a negative, so the only potential is that you had reimbursements before, and an audit might ask you to prove that the new ones are not duplicates of those. In this case, if you have other receipts / proof for all those other reimbursements, they are obviously not duplicates. "Ditto @GradeEhBacon, but let me add a couple of comments: But more relevantly: GradeEhBacon mentioned transaction costs. Yes. Many tax shelters require setting up accounts, doing paperwork, etc. Often you have to get a lawyer or accountant to do this right. If the tax shelter could save you $1 million a year in taxes, it makes sense to pay a lawyer $10,000 to set it up right. If it could save you $100 a year in taxes, paying $10,000 to set it up would be foolish. In some cases the tax savings would be so small that it wouldn't be worth the investment of spending $20 on a FedEx package to ship the paperwork. Inconvenience. Arguably this is a special case of transaction costs: the cost of your time. Suppose I knew that a certain tax shelter would save me $100 a year in taxes, but it would take me 20 hours a year to do the paperwork or whatever to manage it. I probably wouldn't bother, because my free time is worth more than $5 an hour to me. If the payoff was bigger or if I was poorer, I might be willing. Complexity. Perhaps a special case of 3. If the rules to manage the tax shelter are complicated, it may not be worth the trouble. You have to spend a bunch of time, and if you do it wrong, you may get audited and slapped with fines and penalties. Even if you do it right, a shelter might increase your chance of being audited, and thus create uncertainty and anxiety. I've never intentionally cheated on my taxes, but every year when I do my taxes I worry, What if I make an honest mistake but the government decides that it's attempted fraud and nails me to the wall? Qualification. Again, as others have noted, tax shelters aren't generally, ""if you fill out this form and check box (d) you get 50% off on your taxes"". The shelters exist because the government decided that it would be unfair to impose taxes in this particular situation, or that giving a tax break encourages investment, or some other worthy goal. (Sometimes that worthy goal is ""pay off my campaign contributors"", but that's another subject.) The rules may have unintended loopholes, but any truly gaping ones tend to get plugged. So if, say, they say that you get a special tax break for investing in medical research, you can't just declare that your cigarette and whiskey purchases are medical research and claim the tax break. Or you talked about off-shore tax havens. The idea here is that the US government cannot tax income earned in another country and that has never even entered the US. If you make $10 in France and deposit it in a French bank account and spend it in France, the US can't tax that. So American companies sometimes set up bank accounts outside the US to hold income earned outside the US, so they don't have to bring it into the US and pay the high US tax rate. (US corporate taxes are now the highest of any industrialized country.) You could, I suppose, open an account in the Caymans and deposit the income you earned from your US job there. But if the money was earned in the US, working at a factory or office in the US,  by a person living in the US, the IRS is not going to accept that this is foreign income." "They're hiding income. The IRS is a likely candidate for who they are hiding it from but not the only option. Another possibility that comes to mind is someone who had a judgment against them--a check made out to ""cash"" could be handled by someone else and thus not ever appear in their bank accounts." There are still ways that the default values on the W4 can lead you to get a refund or owe the IRS. If there was a big delta in your paychecks, it can lead to problems. If you make 260,000 and get 26 paychecks that means each check had a gross of 10,000. Your company will withhold the same amount from each check. But If you earned a big bonus then the smaller regular paychecks may not have been withholding enough.  When bonus checks are involved the payroll office has to treat them as irregular pay to be able to make it work out. Some companies don't do this, so you may under or over pay during the year. If you changed companies during the year, this can lead to under or over payment. The lower paying company would not know about the higher rate of pay at the other company. so at one you would under pay, and the other you would over pay. There are also social security issues with more than one employer. Years ago, I had a tenant who bounced a check now and then. I started going to the bank where his account was. With my ID they were agreeable to cashing the check against his account. The teller first checked his balance and only cashed when there were enough funds. One time he was $10 short. I wrote a deposit slip and added the $10 it took to clear the check.  As they say, your mileage may vary, I hear some banks won't even break a large bill for a non customer. "Not necessarily.  The IRS deals with income taxes.  I'd have to run the numbers, but I'm not sure if this would short the IRS versus deducting wages paid at time and a half.    Usually, a state's Department of Labor (or similar) would go after him for something like this.  Also, this sounds like plain old fraud, so a criminal charge could be brought.  What's also interesting is how the franchise's CPA and/or Subway's corporate accounting handled this.  ""Phantom"" employees are a big no-no, but are more commonly used to hide embezzlement.  There are a number of tests auditors are supposed to perform to weed out phantom employees.  I wonder if they did and covered it up or if they never bothered to test.  Either is bad.  /lawyer and accountant" The advice is always to not get a big refund from the IRS, because that is giving them an interest free loan. You actually have an opportunity to get an interest free loan from them.  When you file your taxes for 2013 note how much you paid in taxes. Not the check you had to send in with your tax form or the refund you received, but the total amount in taxes you paid. Multiply that amount by 1.1 or (110%). For example $8,000 * 1.10 = $8,800. When you get your paychecks in 2014 you goal is to make sure that your federal taxes (not state, Social security or medicare) taken from your paycheck will get you over that number $8,800 /26 or ~350 a paycheck. Keep in mind that the later you start the more each check needs to be. You will owe them a big check in April 2015. But because of the 110% rule you will not owe interest, penalties, or have to deal with quarterly taxes. The 110% rule exempts you from these if you end them 110% as much a you paid in taxes the previous year. Note that no matter how you pay your taxes for 2014: big check now, extra per paycheck, or minimum now; you will have to watch your withholding during 2015 because the 110% rule won't protect you. "Hearing somewhere is a level or two worse than ""my friend told me.""  You need to do some planning to forecast your full year income and tax bill. In general, you should be filing a quarterly form and tax payment. You'll still reconcile the year with an April filing, but if you are looking to save up to pay a huge bill next year, you are looking at the potential of a penalty for under-withholding.  The instructions and payment coupons are available at the IRS site.  At this point I'm required to offer the following advice - If you are making enough money that this even concerns you, you should consider starting to save for the future. A Solo-401(k) or IRA, or both. Read more on these two accounts and ask separate questions, if you'd like." In regards to your 1st question, if you are a US resident (according to IRS rules) and you have any foreign bank accounts, then you need to file a FBAR form for every year in which any of these accounts has more than $10,000. This is the way that IRS keeps track of substantial amounts of money kept by US residents in foreign accounts. US bank deposits over $10K only need to be reported to FinCEN (Financial Crimes Enforcement Network- a bureau of the US Department of Treasury) if the deposits are made in cash or other money instruments where the source cannot be traced (money orders, traveler checks, etc). Regular checks and wires don't need to be reported because there is a clear bank trail of where the money came from. If your family member is giving you money personally (not from a business) from a bank account which is outside of the US, then you only need to report it if the amount is over $100K. Note, you would need to report that regardless of whether the money was deposited into your US bank account, or paid directly to your credit cards on your behalf, and there are stiff penalties if you play games to try to avoid reporting requirements. Neither deposit method would trigger any taxable income for the scenario you described. If you are going to put it into a banking system, just deposit it. Why did breaking it up even cross your mind? Like what would that even have accomplished, so you could pretend like you started moonlighting as a club bouncer if you were ever casually asked by a bank teller or federal agent? If you have to ever account for the source of your money, you will have to account for it regardless. You shouldn't worry about things that may trigger higher scrutiny on you, because it is pretty random. The financial institution may file a suspicious activity report any time they feel like it (which they routinely do without the customer's knowledge, for a wide range of reasons), and actually attempting to break it up into smaller deposits would mean the suspicious activity report would escalate into criminal charges. And regarding the IRS, if they ever audited you then you will still have to account for that $25,000 no matter what you did with it. "That's accurate.  Here is another risk with the current checking system, which many people are not aware of: Anyone who knows your checking account number can learn what your balance in that account is.  (This is bank-specific, but it is possible at the major banks I've checked.) How does that work?  Many banks have a phone line where you can dial up and interact with an automated voice response system, for various customer service tasks.  One of the options is something like ""merchant check verification"".  That option is intended to help a merchant who receives a check to verify whether the person writing the check has enough money in their account for the check to clear.  If you select that option in the phone tree, it will prompt you to enter in the account number on the check and the amount of the check, and then it will respond by telling you either ""there are currently sufficient funds in the account to cash this check"" or ""there are not sufficient funds; this check would bounce"". Here's how you can abuse this system to learn how much someone has in their bank account, if you know their account number.  You call up and check whether they've enough money to cash a $10,000 check (note that you don't actually have to have a check for $10,000 in your hands; you just need to know the account number).  If the system says ""nope, it'd bounce"", then you call again and try $5,000.  If the system says ""yup, sufficient funds for a $5,000 check"", then you try $7,500.  If it says ""nope, not enough for that"", you try $6,250.  Etcetera.  At each step, you narrow the range of possible account balances by a factor of two.  Consequently, after about a dozen or so steps, you will likely know their balance to within a few dollars.  (Computer scientists know this procedure by the name ""binary search"".  The rest of us may recognize it as akin to a game of ""20 questions"".) If this bothers you, you may be able to protect your self by calling up your bank and asking them how to prevent it.  When I talked to my bank (Bank of America), they told me they could put a fraud alert flag on your account, which would disable the merchant check verification service for my account.  It does mean that I have to provide a 3-digit PIN any time I phone up my bank, but that's fine with me. I realize many folks may terribly not be concerned about revealing their bank account balance, so in the grand scheme of things, this risk may be relatively minor.  However, I thought I'd document it here for others to be aware of."