A merchant requests that checks be made out to “Cash”. Should I be suspicious?
There are legitimate reasons: I wouldn't jump the gun and assume that this person is avoiding taxes, etc. Barbers are usually licensed professions. Since it's generally a cash business, they tend to get audited more often by the tax authorities. That said, I wouldn't pay her with a check -- you have no idea who is actually cashing the check, and you could run into issues with unknown third parties misusing your account information. "There are benefits associated with a cash only business (the link states a few). However checks made out to ""cash"" don't reap those benefits listed. For anyone on SE to say your barber hides revenue from the IRS would just be speculation.  With that said there are a great number of disadvantages for a cash only business. And from my experience, a business that goes out of their way to take cash only can be a little suspicious. Luckily you are not committing any crimes or fraud by paying her cash." "To put a positive spin on the whole thing, maybe it's a small family shop, and having the check made out to ""cash"" means that your barber can hand it to someone else without the need to countersign. Or maybe his last name is ""Cash"" - there was a pretty famous singer who fit that description. Either way, it's not your place to nanny his finances." "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." If the business owner doesn't want you to pay him directly, the only reason I can think of is breaking a law. It can be because the business doesn't legally exists, or because the barber wants to evade taxes, or because he doesn't pay his child support or doesn't want his income to be apparent to his debtors in a bankruptcy proceedings. Either way, stinks.
The issue yo have to consider is that under many state laws, you must give a merchant three opportunities to correct an issue before you can sue them, so check with your state before considering that option. Here's a link to the Federal Trade Commission's warranty information page, which may give you some ideas about what your options are. Keep in ind, if you let someone else work on the computer rather than the store you bought it from, you might give the guy a valid claim in court to throw out your lawsuit!  Many times, warranties will spell out the conditions under which repair work can or must be done, so make sure you follow every step to the letter in order to preserve your claim. I would strongly suggest that you start creating a paper trail for your claim.  Start by writing a very precise and detailed letter to the store owner, with copies of all relevant documents (your receipts, warranty papers, etc.) included.  Explain the entire history, including what steps you've taken to date to get him to honor the warranty.  Offer him the option to let you take the computer to another shop for repairs at his expense.  Then, send the letter by certified mail, return receipt requested, to the store owner so that he can't deny receiving your letter.  This is all in order to make the best case you can for your claim just in case you do have to sue him. Do not take the computer to anyone else until or unless he tells you in writing that he is willing to let you do that.  You don't want to risk him arguing that the other shop is responsible for the problems now. I hope this helps. Good luck! "You should immediately tell your bank you've been scammed, request for the transactions' cancellation or revocation and get back most - if not all - of the money transferred. I've placed numerous orders online in the past and was always very careful about their trace-ability but I have to admit once I acted carelessly and got scammed. I didn't think of it much before placing an order for a very low priced laptop through a private seller on Amazon. I'd never purchased anything this way before but thought ""Amazon will protect me if anything goes wrong..."" so I sent an e-mail to the seller. He gave me his bank details (with Spanish IBAN) via a non-suspicious e-mail with the usual logos and e-mail address domain name, made the payment and guy came back to me saying he'll ship the laptop once he sees the funds received. Waited max. 2 days, trying to contact him but no response. Contacted Amazon giving the seller's ID and the ""transaction""'s ID I'd received from him and they told me there's nothing they can do as that transaction is not recorded on their systems. Immediately after realizing I've been scammed and done my goof, I contacted my bank via e-mail explaining the situation. I was informed that the transaction can be cancelled but they cannot guarantee the return of the entire amount. After 2-3 days, I saw my balance richer by €950 and the payment I'd made to the scum was €1,000. I'd highly recommend that you check the fraud protection policy of your bank and in case there's something that can be done, then just get in contact with them explaining the situation." "withdraw in cash - bank reports it to IRS no matter what. Would this   affect my tax filing in the coming year? No, and no. The bank doesn't report to the IRS. In the US - the bank will probably report to FinCEN. It has nothing to do with your tax return. withdraw in check - bank does not seem to report it. Is this correct? Doesn't have to. Still might, if they think it is a suspicious/irregular activity. wire-transfer to another person's account - would this always be   slapped with a ""gift tax""? If this is a gift it would. Regardless of how you transfer the money. Is it? Answers to your follow up questions: In the US, what documents do we need to prepare in case our large sum   withdraw from the bank triggers a flag in relevant government (local   and/or federal) divisions and they decide to investigate? Depending on what the investigators request. FinCEN would investigate money laundering, the IRS would investigate tax evasion, the FBI would investigate terrorism sponsorship, etc. Depending on who's investigating and what the suspicions are - different documents may be required. But the bottom line is that you should be able to explain the source of the funds and the destination. For example ""I found $1M in cash and sent it to some drug lord because he's such a good friend of mine"" will probably not fly. Does the (local/federal) government care if we stash our money (in   cash or check) under our mattress, if we purchase foreign properties   (taxable? documents needed for proof?), or if we give it away (to   individuals or organizations - individual: a gift tax, organization:   tax waivable) ? The government cares about taxes, and illegal activities. Stashing money under a mattress is not illegal, but earning cash and not paying income tax on it usually is. In many cases money stashed under the mattress was obtained illegally and/or income taxes were not paid. It seems that no matter what we do (except spreading thin our assets   to multiple accounts in multiple banks), the government will always be   notified of any large bank transaction and we would be forever flagged   since. Is this correct ? Yes, reportable transactions will be reported. Also spreading around in multiple accounts/transactions to avoid reporting is called ""structuring"" and is on its own a crime. This is for cash/cash equivalent transactions only, of course. Not sure about the ""forever flagged since"", that part is probably sourced in your imagination." Structuring, as noted in another answer, involves breaking up cash transactions to avoid the required reporting limits.   There are a couple of important things to note.   And, the biggest caveat - there have been many cases of perfectly legitimate transactions that have fallen foul of the reporting requirements.  One case springs to mind of a small business that routinely deposited the previous day's receipts as cash, and due to the size of the business, those deposits typically fell in the $9,000-$9,500 range.  This business ended up going through a lot of headaches and barely survived.  Some don't.   A single batch of transactions, if it is only 2 or 3 parts and they are separated by reasonable intervals, is not likely in and of itself to be suspicious.  However, any set of such transactions does run the risk of being flagged.   In your case, you also run afoul of the Know Your Customer rules, because it's not even you depositing the cash - it's your friend.  (Why can your friend not simply write you a check?  What is your friend doing with $5k of cash at a time?  How do you know he's not generating illegal income and using you to launder it for him?)  Were I your bank, you can be very certain I'd be reporting these transactions.  Just from this description, this seems questionable to me.   IRS seizes millions from law-abiding businesses "This is most likely protecting Square's relationship with Visa/Mastercard/AMEX/etc. Credit card companies typically charge their customers a much higher interest rate with no grace period on cash advances (withdrawals made from an ATM using a credit card). If you use Square to generate something that looks like a ""merchandise transaction"" but instead just hand over a wad of banknotes, you're forcing the credit card company to apply their cheaper ""purchases"" interest rate on the transaction, plus award any applicable cashback offers†, etc. Square would absolutely profit off of this, but since it would result in less revenue for the partner credit card companies, that would quickly sour the relationship and could even result in them terminating their agreements with Square altogether. † This is the kind of activity they are trying to prevent:  1. Bill yourself $5,000 for ""merchandise"", but instead give yourself cash.  2. Earn 1.5% cashback ($75).  3. Use $4,925 of the cash and a $75 statement credit to pay your credit card statement.  4. Pocket the difference.  5. Repeat. Note, the fees involved probably negate any potential gain shown in this example, but I'm sure with enough creative thinking someone would figure out a way to game the system if it wasn't expressly forbidden in the terms of service" Just have the associate sign the back and then deposit it.  It's called a third party cheque and is perfectly legal.  I wouldn't be surprised if it has a longer hold period and, as always, you don't get the money if the cheque doesn't clear. Now, you may have problems if it's a large amount or you're not very well known at the bank.  In that case you can have the associate go to the bank and endorse it in front of the teller with some ID.  You don't even technically have to be there.  Anybody can deposit money to your account if they have the account number. He could also just deposit it in his account and write a cheque to the business. I would go to the bank and just express the concern that the check sent to you might not fully clear. You don't want to spend it until you're sure it cleared. I'd ask for a manager to tell you when it will clear, then confirm after that date that it's cleared, with the same guy.  Perhaps someone in the industry can explain how long the bank has before deciding the check is bad. 10 days? 2 weeks? Really, it should either clear or bounce by the second night.  I'd not risk doing this for anyone. Anyone I know personally can cash their own check, and I'd not get involved with anyone I don't know on a financial matter like this. EDIT - See Littleadv comment below. Good checks clear fast, a forged check has time for the victim to go to the bank and challenge the signature and cashing of the check. The victim can have 60 days to do this. That's the issue, I am wrong, the bank manager couldn't confirm the check was good so soon. http://www.consumerismcommentary.com/buying-house-with-cash/ It looks like you can, but it's a bad idea because you lack protection of a receipt, there's no record of you actually giving the money over, and the money would need to be counted - bill by bill - which increases time and likelihood of error.   In general, paying large amounts in cash won't bring up any scrutiny because there's no record. How can the IRS scrutinize something that it can't know about? Of course, if you withdraw 200k from your bank account, or deposit 200k into it then the government would know and it would certainly be flagged as suspicious.