https://bugs.winehq.org/show_bug.cgi?id=39293
--- Comment #6 from Austin English austinenglish@gmail.com --- (In reply to Marco from comment #5)
The issue can be confirmed with current Wine 1.9.8 on Debian Jessie, 32 bit, 4.3 Kernel, current Notepad++ 6.9.1 and NppExec 0.5.3.
Feedback from the developer of the NppExec plugin and further analysis can be found in https://sourceforge.net/p/npp-plugins/discussion/672146/thread/405041c6/#2b6...
Following assertion failure in the "richedit" component seems to be related to the issue: an/.wine/dosdevices/c:/Program Files (x86)/Notepad++/notepad++.exe: caret.c:231: ME_GetCursorCoordinates: Assertion `~para->member.para.nFlags & 0x01' failed.
Does 'winetricks riched20' help?