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Hi Tah. I'm Greg, an installation specialist, 10 years Windows MVP, and Volunteer Moderator here to help you.
I'll give you everything possible to try for headset problems so at least something will work. If you need help performing any steps I am standing by here to help:
First try the steps here:
https://www.maketecheasier.com/fix-headphones-n...
https://www.windowscentral.com/setting-your-hea...
https://www.lifewire.com/fix-headphones-not-wor...
https://www.thewindowsclub.com/headphones-not-w...
https://merabheja.com/fix-no-speakers-or-headph...
https://troubleshooter.xyz/wiki/fix-headphones-...
Go to Settings > Devices > Autoplay to look for the device and change the default behavior in it's Dropdown Menu.
Right click Volume icon in System Tray at right end of task bar, Open Sounds Settings, in dropdown menus at top make sure Headphones are selected and Connected for both Playback and Recording Default Devices.
If not again right click Volume icon in System Tray to choose Troubleshoot sound problems.
See all ways (including manufacturer-specific) to re-enable the "Which device did you plug in" popup which can solve headset issues:
https://windowsreport.com/you-just-plugged-unpl... (avoid ad links)
https://h30434.www3.hp.com/t5/Notebook-Audio/En...
https://forums.tomshardware.com/threads/how-do-...
https://www.dell.com/community/Windows-10/How-g...
https://answers.microsoft.com/en-us/windows/for...
Go to the Device Manager reached by right clicking the Start button, choose Sound controller device, on Driver tab choose Roll back or Uninstall, restart PC using keyboard to Ctrl Alt Del, on blue screen tab to Power Icon in bottom right, press Enter, arrow down to Restart, press Enter to restart to reinstall the driver.
Do the same for the headset device and/or it's microphone.
Update the Sound driver from the PC or Device maker's Support downloads web page. While there also check that the Chipset, BIOS, Display, USB, Network and all other drivers are the most current.
Sometimes it helps to unpair or disconnect all other Bluetooth devices from the PC in Bluetooth settings, then try again to connect the headset.
If this was caused by Windows Update(s) then you can check which were installed at Settings>Update & Security>Windows Update under Installed Updates, then uninstall them from the link there, and hide with the Hide Updates tool downloaded from here: http://download.microsoft.com/download/f/2/2/f2...
You can also use System Restore to get before the problem began, then check for Updates with the Hide Update tool and hide them:
http://home.bt.com/tech-gadgets/computing/how-t...
If this was caused by a Version Update then for 10 days you can roll it back in Settings>Update & Security>Recovery and then hide it until it matures using the Hide Updates Tool which is explained more here:
https://www.howtogeek.com/223864/how-to-uninsta....
To check over the integrity of your install go over this checklist to make sure the install is set up correctly, optimized for best performance, and any needed repairs get done: http://answers.microsoft.com/en-us/windows/wiki...
Start with Step 4 to turn off Startup freeloaders which can conflict and cause issues, then Step 7 to check for infection the most thorough way, then step 10 to check for damaged System Files. Then continue with the other steps to go over your install most thoroughly.
If nothing else helps you can run a Repair Install by installing the Media Creation Tool and choosing from it to Upgrade Now. This reinstalls Windows in about an hour while saving your files, apps and most settings, solves many problems while also bringing it up to the latest version which you need anyway and by the most stable method.
http://windows.microsoft.com/en-us/windows-10/m...
If you want to report this to Microsoft use the Feedback Hub app in Start Menu where developers are tasked to process consumer feedback. They will not even see it here. This is a tech forums staffed mostly by volunteers trying to help others with your problems.
If you want to post back a Share link from your Feedback here others who see this thread can vote it up and add to it. If you are an Insider I can also vote it up with my MVP badge and track the issue for you.
I hope this helps. Feel free to ask back any questions and keep me posted. If you'll wait to rate whether my post helped you, I will keep working with you until it's resolved.
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