Why will my headphones not play audio?

I would suggest you get a new pair, see if that pair that isn't working works on a different device, or clean the headphones and the headphone jack. If any of these work, then I will feel useful!

It could also be a DRM issue that prevents playback when something is plugged into the headphones jack. I can hear my Amazon Music and alerts just fine, but when I try text-to-speech or the add-on audible version of a particular audiobook, it will not play, except over the tiny Kindle Fire speaker. It worked a couple of weeks ago, but I noticed that my Fire updated itself on May 5th. I did download the same book (but not the Audible version) on a newer Kindle I got on eBay last weekend, so maybe there's a limit on the number of devices authorized. It kind of flies in the face of customer loyalty, as the authorization ought to just transfer to the current device.

I had this problem and found out that it was related to how well the earbuds were inserted into the device. Pushing down again after inserting the plug helped

Check to see if anything is in the hole where you plug then take that out the but the plug in if that doesn't work try rubbing it on you butt hole because that works