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I know it's required to fill FinCEN 105 for $10,000+ flying internationally. However, I was wondering about my particular situation. I live in the US and plan to sell my art/merch in foreign countries at events/concerts when they eventually reopen post-COVID. I should fill the FinCEN form returning to the US but if I'm stopped and questioned about how I obtained the money, I would answer truthfully that I sold my art but is that something that could be deemed illegal or suspicious?

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    Do you have a business established (do you sell in the US as well)? Does you visa in the other country/countries allow you to operate a business there? Can you show that you paid the appropriate taxes on those overseas earnings? Those would all establish that you have a bona fide business. You are still better using appropriate international banking methods to move the money around though.
    – Jon Custer
    Jul 7, 2021 at 16:00
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    Is there a specific reason to use cash? Nowadays, the normal way to conduct business is to use bank transfers, credit cards, or other digital means. Using lots of cash just raises a lot of red flags about where the money is coming from and where it's going to.
    – jcaron
    Jul 7, 2021 at 16:10
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    Bear in mind that you will be importing goods to other countries to sell. You will have to declare them to Customs at the time of importation and pay all applicable taxes. The Customs allowances are applicable for goods for your personal use and not goods for a commercial purposes.
    – canonacer
    Jul 7, 2021 at 17:08

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IANAL and it is best for you to confirm with a lawyer since this answer is not legal advice.

Yes and no. You are indeed allowed to bring a large amount of cash and you are obliged to disclose it. Doing so is therefore legal but the reason they ask to disclose large amounts of cash coming into the country is that this is often related to suspicious activity.

When you declare the amount, you will be thoroughly questioned and it is the custom officer who decides what proofs to ask and whether to escalate the disclosure. Bear in mind that, even if you pass through customs with minimal hassle, you are likely to be questioned every time you cross the border in the future even if you do not declare such amount on subsequent trips because this will be in your history. I know people for which this has been happening after making just one such declaration.

It is better to not fly with the actual cash and do a wire transfer. You will still be importing the same amount but there are fewer suspicions with traceable transfers than cash. An accountant should be consulted to know if you will have to pay taxes on your gains. This varies by jurisdiction but usually there is a threshold below which no tax is claimed and above that a lot of factors apply.

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    Note that when you import the money via wire transfer, it will be the bank doing the FinCEN declaration...
    – jcaron
    Jul 7, 2021 at 16:11
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You must be prepared to justify your possession of the cash, i.e., demonstrate that the cash is the result of legal activities. Paperwork (ledgers, account books, bank statements, etc.) will be more persuasive than words. But it is impossible to predict whether whatever documents you carry will be enough to satisfy the authorities; there are too many variables.

Guessing wrong will have really bad consequences. Thus, it'd be best to not carry cash. If you guess wrong, and they think you're trying to pull the wool over their eyes, the currency could be seized by any of the border authorities you encounter.

You're much better advised to transfer funds in another manner.

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