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Apart from directly buying digital music files, there are a few ways in which you could possess such files legally (at least in my country):

  1. Creating them from CDs you legally own, to make listening on the go more convenient. I believe this is legal in the U.S.
  2. Receiving them from a close acquaintance, who have a legal right to possess those files. This is legal in my country, but I'm not so sure it is in the U.S.

While at least the first category (as far as I know) is legal in the U.S. as well, there really is no way for border agents to know, for any given music file, whether I'm legally allowed to have it or not.

If I, a foreign national from a visa waiver program country, were to arrive from overseas at a U.S. airport while carrying a phone, laptop or other storage device containing files in either of these two categories, how likely am I to get in trouble (as in, getting held up or detained, having devices confiscated, etc.) with the CBP?

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    I would think the chances they would even investigate that are close to 0. – jcaron May 25 at 11:23
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    Have you done any internet search on this? As almost everybody has some music on their phone and/or laptop, if the CBP is confiscating their devices in high percentages it would show up online. – Willeke May 25 at 11:23
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    US CBP is really only interested in counterfeit goods intended for sale (e.g. fake DVDs etc.). Those get shipped in containers, as your luggage just won't hold 100,000 DVDs... – Michael Hampton May 25 at 16:58
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    @Mazura Read down to the bottom of that article. While what you state is normally true for the United States, border searches are a notable exception to the requirement for probable cause. – reirab May 25 at 20:18
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    @Mazura Wrong. There has been no Supreme Court case over the search of electronic materials when subject to the border search exception. Case law is currently split on that topic. – user71659 May 25 at 20:18
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how likely am I to get in trouble (as in, getting held up or detained, having devices confiscated, etc.) with the CBP?

Extremely unlikely. I have carried music files across borders hundreds of times into dozens of countries (as do millions of other people every day) and I've never seen or heard anything like this. The CBP has no way of knowing whether your underwear has been legally acquired but they don't care about that either. Your music file are no different.

The only potential scenarios which may trigger an interaction is if the music files contain "illegal", "censored" or "morally undesirable" content that is not allowed or questionable in the destination country AND the immigration officer has reason to suspect you are in possession of such content. The US has a very broad definition of "free speech" which is protected by the first amendment, so any content that violates that would have be pretty extreme.

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    "Pretty extreme" would involve getting enough investigation to serve a warrant. You'll have to do very serious stuff before that happens, like the Silk Roads guy. Napster wasn't even taken down by the government, but by private companies suing them, and it was a platform that distributed illegal stuff. – Nelson May 27 at 8:48
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    @Nelson “[Napster] was a platform that distributed illegal stuff.” No it wasn’t (any more than Twitter is), otherwise it likely would have been taken down by the government. – Konrad Rudolph May 27 at 11:50
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    "The US has a very broad definition of "free speech" which is protected by the first amendment" - Non-citizens don't share all the rights of citizens under the U.S. Constitution. Additionally foreign visitors are subject to immigration law, under which the executive branch has broad (although not completely arbitrary) authority to determine whether it wants them in the country or not. And, until visitors have actually passed through immigration control and/or crossed the border, they aren't technically on U.S. soil and the U.S. Constitution may not yet grant them rights and/or protection. – HBruijn May 27 at 12:27
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    @HBruijn You are on American soil the second you your feet touch the ground when you step off the plane. Airports – including airside areas – are built on sovereign territory. It is up to the host country whether or not special rules apply to airside areas. If such special rules do apply (I’m not sure they do in the US), then there are certain rights and obligations local law does not grant/impose upon you until you have cleared immigration; but you are still on host country soil while you’re airside, and in general, you still need to abide by host country laws. – Janus Bahs Jacquet May 27 at 15:46
  • @JanusBahsJacquet Some constitutional rights, such as the prohibition against unreasonable search, do not apply at ports of entry in the US regardless of your citizenship. Further, border agents have extensive power (routinely abused) within 100 miles of any border (covering almost 2/3 the US population). For more information see this ACLU page and "The US-Mexico Border: Where the Constitution Goes to Die". – Curt J. Sampson May 28 at 0:52
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There really is no way for border agents to know, for any given music file, whether I'm legally allowed to have it or not. ... How likely am I to get in trouble (as in, getting held up or detained, having devices confiscated, etc.) with the CBP?

There is no customs duty on electronic files. Furthermore, there is an important principle in modern law called presumption of innocence. Because of this, they cannot treat the mere possession of the files as evidence that you have committed a crime any more than they could with anything else in your possession, as implied in the other answer.

To charge you with a crime in connection with those files, they have to have a credible chance of showing in court that you committed such a crime. They cannot just ask you to show that you didn't do so.

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    IIRC, those entering under VWP waive away their right to a trial should a CBP agent choose to deport them, meaning that they can be deported/denied entry for almost any reason. Though it's been a few years since I last went through the process, so I might be wrong. – user82529 May 26 at 19:33
  • @Rogem no, you are more or less correct. But they waive the right to an immigration hearing before a judge on their removal under immigration law. This is not a criminal matter, and the burden of proof in such a hearing is on the traveler, not the government. My point here is to look at this in the context of criminal law. Someone showing up with obviously stolen goods has more to be worried about than just refused entry and removal; criminal charges would be likely, and that would involve arrest and a right to a jury trial. – phoog May 27 at 20:28
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Theoretically, custom officials have the right to inspect your storage devices for illegal content. I wouldn't worry about files that you made yourself, but files coming from the Internet (or from your acquaintances who could've also put the files they shared with you on the Internet or gotten them from there in the first place) could be easily identified as illegal content by checksum matching. IANAL, but as far as I know, having a copy of a copyrighted file which is being illegally distributed and was never released legally may result in you having to explain where you got it from.

Of course, chances of this happening are close to nil in practice, but I still wouldn't openly carry files those provenance I'm not 100% certain about.

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