@myfirstnameispaul ,
somehow Notepad++ has reverted to essentially a brand-new install, so no settings, sessions, nothing.
It may be that you just have to start reconfiguring from there.
But you can try to share your ?-menu’s Debug Info, and we can see if we can point you in the right direction.
But we are not experts on Wine here, so we won’t necessarily know how to map concepts from Windows to Wine: For example, is /home/username/.wine/drive_c/users/username/Application Data/ the Wine equivalent of c:\ProgramData\ ? Or of c:\users\username\AppData\ ? Or of c:\users\username\AppData\Roaming\ ? Or of c:\users\username\AppData\Local\ ? Because which of those it’s the equivalent of will determine whether your config files are in the right place. Under supported Windows OSes, the Notepad++ configuration goes under %AppData%\Notepad++, which is usually c:\users\username\AppData\Roaming, not the c:\users\username\AppData\ that most people misinterpret the %AppData% as meaning. So if /home/username/.wine/drive_c/users/username/Application Data/ is exactly equivalent to c:\users\username\AppData\ , then your Notepad++ is not in the right directory, and it should be c:\users\username\AppData\Roaming\Notepad++\ … But that’s a big IF, that we cannot answer.
And maybe run Settings > Edit Popup ContextMenu, and see what the path is of the contextMenu.xml that it loads – because that should be the location where all your other config files go as well.