The play button is getting yet another upgrade from the Internet: the ability to function in sync across multiple devices. Instead of only being able to listen to a song on your own computers, a few apps can cue up that tune on other gadgets–in effect, turning them into Internet-connected speakers.

Is that legal? You’ve heard this before in copyright debates: It depends!

The best-known implementation of the concept is Samsung’s free Group Play app, which comes preinstalled on its Galaxy S 4 but also works on other recent Samsung phones and tablets.

It’s pretty straightforward to set up: Open the app and tap “Create group” on your device, choose a song and then a second phone within WiFi range can have the same tune streaming in sync–with its left and right channels sent separately to each device for a proper stereo effect.

The default setting requires you to set a numeric passcode for the group, with up to nine other devices allowed, but you can assign a single-digit passcode or make the group open. You can also share pictures and documents or play games this way.

Last weekend, I saw a similar concept at the Day of Fosterly startup conference: a Web app called Speaker Blast, which lets you upload a song to a server and then have it play through multiple Web browsers at a preset time.

Two tests of this app (still in private beta) did not work quite as smoothly. The desktop, laptop and iPad evidently did not have the exact same time, resulting in playback a tic out of phase–as if I were hearing “Radio Free Europe” played not by R.E.M., but by a cover band needing more rehearsal.

A third app, Seedio, offers similar group-playback features on iOS, but I haven’t tried that yet.

All of these products intersect with a core concept of copyright law: the restriction on the “public performance” of a copyrighted work without a proper license.

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Those songs you paid for and downloaded legally from the likes of Amazon and iTunes? A federal district court ruling yesterday held that you don’t really own them, in the sense of having the basic ownership right of being able to sell them.

Judge Richard Sullivan’s decision in Capitol Records v. ReDigi isn’t going over well with digital-liberty types. It shouldn’t. It’s another example of trying to fit a digital case into an analog frame, at the cost of denting some logic along the way.

The case started when ReDigi opted to set up a clearinghouse for iTunes purchases. You’d use its music-management app to verify which of your files had come from Apple’s store and transfer those to its online storage (deleting your local copies in the process); from there, you could stream them to your computer or put them up for sale to other ReDigi users (making them unavailable to you in the process).

If this transaction involved a CD, nobody would question its legality. You bought the disc and own it; U.S. copyright law’s first-sale doctrine guarantees your right to sell that physical object to somebody else.

But the relevant section of copyright law is not so clear about the status of digital downloads. (You can’t point to Apple’s terms of sale for clarity in ReDigi’s iTunes-specific case; they don’t explicitly bar resale or call a music purchase a license, unlike Amazon’s.) Facing that unsettled situation, Sullivan read those provisions to favor Capitol Records: a transfer of a digital music file over the Internet is not a transfer but a reproduction, legally speaking.

“It is beside the point that the original phonorecord no longer exists,” wrote Sullivan. “It matters only that a new phonorecord has been created.”

(I hear some of you protesting already: “But… but… what difference does it make? The supply of music is the same!” I hear you.)

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