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.
"If you sign the check ""For Deposit Only"", the bank will put it in your account. You may need to set up a ""payable name"" on the account matching your DBA alias. However, having counted offerings for a church on several occasions, I know that banks simply have no choice but to be lax about the ""Pay to the Order Of"" line on checks. Say the church's ""legal name"" for which the operating funds account was opened is ""Saint Barnabas Episcopal Church of Red Bluff"". You'll get offering checks made out to ""Saint Barnabas"", ""Saint B's"", ""Episcopal Church of Red Bluff"", ""Red Bluff Episcopal"", ""Youth Group Fund"", ""Pastor Frank"", etc. The bank will take em all; just gotta stamp em with the endorsement for the church. Sometimes the money will be ""earmarked"" based on the payable line; any attempt to pay the pastor directly will go into his ""discretionary fund"", and anything payable to a specific subgroup of the church will go into their asset account line, but really all the cash goes directly to the same bank account anyway. For-profit operations are similar; an apartment complex may get checks payable to the apartment name, the management company name, even the landlord. I expect that your freelance work will be no different." 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. I've kind of been there myself.  I stretched my finances for the deposit on a house, and lived off my credit card for a few months to build up what I was short on the deposit.  Add some unexpected car repairs, and I ended up with £10k on the card.  The problem I had then was that interest on the card ran at around 20%, and although I could meet the interest payments I couldn't clear the £10k. I simply went and talked to my bank.  In the UK there are some clear rules about banks giving customers a chance to restructure their debts.  That's the BANK doing it, not some shady loan-shark.  We went through my finances and established that in principle it was repayable.  So I got a 2-year unsecured loan at around 5%, cleared the card, and spent the next 2 years paying off a loan that I could afford.  My credit score is still aces. Forget the loan-sharks.  Talk to your bank.  If they're crap, talk to another bank.  If no bank is going to help you, consider bankrupcy as per advice above.  Debt restructuring companies are ALWAYS a con, no exceptions. Money laundering alarms would definitely be raised, way before you walking in with the cash to deposit. Every cash transaction over $10K will be reported by the bank (and not only banks have to report), so the report will be sent when you withdraw the money, as well. But if the money is legitimately yours and you can show the sources, then you shouldn't be worried. There's no law against having cash. Its just very hard to track down the cash money sources, and if someone asks you and you cannot show the proofs - the problem would definitely be yours. "Well a definitive answer would require a lot of information.  Instead of posting that kind of info online, you should take a look at the instructions for Form 2210 and in particular ""Schedule AI -- Annualized Income Installment Method,"" which corrects the penalty for highly variable income.   Using this form you will likely be able to avoid the penalty, but it is hard to know for sure." The $10,000 mark is not a ceiling in importing cash, but rather a point where an additional declaration needs to be made (Customs Form 4790). At 1 million, I suspect you might be in for a bit of an interview and delay. Here's an explanation of what happens when the declaration isn't made: https://www.cbp.gov/newsroom/local-media-release/failure-declare-results-seizure-24000-arrest-two "Let me do the math. .6% * (not large) = really tiny. Since ""not large"" = ""small"" , etc.  I suggest that even a small chance that you need to explain this to anyone in the future is a sign to avoid the risk. Yes, there are times that it's illegal. A real estate office may not deposit escrow funds into anything but a segregated escrow account.  In your case, even if legal, it messes up 'the books' and can cost you more in grief than the 'tiny amount' saves you in cash." The money in the checking account was already taxed. It was income this year or last, or a gift from somebody, or earned interest that will be taxed. If it was a deductible IRA you would declare it next April and get a refund from the government.