1

If I have a 3.5 mm jack on both my generic low end gaming monitor and tower, is the sound still being generated by the tower when going through the monitor? Does the monitor likely have its own sound card? And, most importantly, is plugging into either port more beneficial for sound quality?

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It does matter where you plug in the headset.

The GPU produces sound in digital format, then sends it through HDMI/DVI to the monitor (along with the video). A digital-to-analog chip in the monitor then converts this digital signal to analog, while other sound chips in the computer do not take part in this process.

Plugging it to the computer means that a motherboard embedded sound chip does the job. This sound chip, even if a cheap one, has more options to fine-tune the sound, such as the amount of bass. It is also one conversion less in the process, where each conversion means some lose of quality.

Even the choice between front and rear ports may make a difference, if one audio cable from the motherboard to the panel is longer and acts as an antenna with more interference from the other electrical components, if the cables are not shielded. Although the difference is very minor, it may still matter to some.

The quality of the headset in question will also determine if those differences are detectable or not.

3

It might, depending on what you need to use it for. There are a lot of (theoretical) factors that can influence the quality of the output (Harry gives you good examples, see his answer for more details) but they might not be relevant in your case. In my experience, with average hardware, for, let's say, playing games or listening to background music from the web you won't notice any significant difference.

However you should just compare the output of the two jacks yourself. For example play a song or better single frequencies and compare them directly.

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