@shanselman This is mostly suspected to be the problem of the powerhshell.exe as @crramirez mentioned. When executing powershell.exe in wslu, the settings from the console window for PowerShell will be brought to the current window, so I kind of suspecting this is in some level related to conhost.
Powershell sets and resets the system codepage, which it shouldn't be doing. This can cause the fonts to reset to "raster fonts". This isn't something conhost can fix, as it will break compatibility with applications that need the codepage and font to match.