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I have to mindlessly unplug them and plug them back in until it works.
A while ago I got this 3.5mm extension cable so I could use the rear jacks, cause the top one was utterly worn down, and it just refuses to work properly. I know the green jack is for your headphone...
Since you mentioned this started after a Windows Update, that is almost certainly the trigger. We need to force your PC to forget the broken Microsoft driver and reinstall the correct one from your motherboard manufacturer.