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Help Otherwise functional earbuds won't work through a 90-degree adapter

I've been running into a minor but annoying ear bud issue. You know how some ear buds have this button on the cord which you can click a number of times to change the song or podcast you're listening to. I think on my current set it's one click to advance to the next track, and two clicks to back up to the previous one. Or something like that; I'm not really sure because I don't use the feature. And I don't deliberately seek out this feature, but frequently it's present on the only model I can find in the store which is in my price range, has reasonably sturdy construction, and is eligible for in-store replacement.

This, by itself, isn't really the issue. The problem is that I've had three pairs of ear buds with this feature, and none of them would work through a right angle adapter. To understand why I want to use the adapter, you need to picture how the cord runs from the device up to my ears when the device is carried or worn at pockets/waist level. At the jack end, the cord plugs straight down into the top of the phone. From there the wire goes up a couple of inches, then loops down eight or ten inches, then back up to where the cord splits, around my thorax, and then on into my ears. Now picture me walking along like this. The cord tends to swing a bit, and for some reason almost immediately acquires an extra loop or two. As this happens, it often decides to loop around the clip of my carrier, if I'm wearing one. It also tends to get snagged very easily on any protruding object I happen to walk past, for example doorknobs. I also don't like how the movement of the cord near the jack end seems to subject it to constant lateral stress which might lead to an eventual failure of its protective coating, or worse, failure of the jack itself.

In the past I would sidestep this issue by using one or more 90-degree jack adapters (Radio Shack, just shy of $5 each). If my earbuds had a built in 90-degree angle at the jack end, then I'd use one adapter, so the cord could be plugged in unpwards and hang straight down without looping. If the earbuds had a simple straight jack end, then I was using two adapters to achieve the same result, like this. I found that this went a long way to alleviating the looping/snagging/wrapping-around-the carrier-clip issue. With other ear buds that don't have the button I mentioned, this has always worked fine, at least until they wear out, but that's to be expected with cheap buds.

For some reason, though, earbuds with that button simply will not work through the adapters. Or actually, they will work as long as constant pressure is applied to the button. Otherwise the sound is faint and incomplete, as only the most strident trebles (like a violin or a electric lead guitar) will come through.

And I know the problem is not with the right angle adapters, because regular headphones will work just fine. I verified this with a ten-year-old pair of 'phones that I used to work out in, so worn that the foam rubber earpads have started to wear off, and they worked fine. So did a pair of Koss headphones, of similar vintage but in better condition.

Has anyone else noticed this? Is there a way to make any and all ear buds work through jack adapters?
 
Chances are your 90-degree adapters are made for the more common, typical stereo earbuds that only have three contact points on the plug end. Looking at that photo you included in your message, there are four separate contact points on the plug end. Most jacks, and in your situation adapters, are usually designed for just the common stereo earbuds, where there are contacts inside the jack that will match up with the contacts on the end of the plug when fully inserted. The metal contacts simply do not match up correctly when you're using those special earbuds with common devices, they're spaced differently.
https://en.wikipedia.org/wiki/TRS_connector
 
Chances are your 90-degree adapters are made for the more common, typical stereo earbuds that only have three contact points on the plug end. Looking at that photo you included in your message, there are four separate contact points on the plug end. Most jacks, and in your situation adapters, are usually designed for just the common stereo earbuds, where there are contacts inside the jack that will match up with the contacts on the end of the plug when fully inserted. The metal contacts simply do not match up correctly when you're using those special earbuds with common devices, they're spaced differently.
https://en.wikipedia.org/wiki/TRS_connector

Oddly enough I finally noticed this today--there are three tiny black bands on the plug of the ear bud, but the adapters only have two such bands. From the article you linked to I gather that the tip of the plug forms the third or fourth contact point, respectively. Presumably, the next time I need new ear buds I should look for ones with the more typical TRS configuration, and it's a great thing now that I know what to ask for. More often than not, you can either see the plug end in the package, or there will be a picture of it on the box.

Also today, I found a simple workaround by which I can use the adapters with these ear buds. Of course it was too simple for me not to have overlooked it all this time. Simply fastening a twist-tie around the button and its housing and making it sufficiently tight forces the button to remain in the depressed position. The little black tie that usually comes with most ear buds probably looks the best, but any sort of twist-tie will do.
 
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