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When I try to run the .exe, wine pops up and says file not found. When I try to close that window it pops back up several more times. I am running Manjaro and can answer any questions if needed.

 

In debugger I get this:

[02/17/19 00:03:56] - Running wine- start.exe /wait /unix $target (Working directory : /home/lemmeloveyou/.PlayOnLinux/wineprefix/poe/drive_c/users/lemmeloveyou/Start Menu/Programs/Grinding Gear GamesUnable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/encodings/large
Unable to revert mtime: /usr/share/fonts/encodings/large
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/encodings/large
Unable to revert mtime: /usr/share/fonts/encodings/large
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/encodings/large
Unable to revert mtime: /usr/share/fonts/encodings/large
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/encodings/large
Unable to revert mtime: /usr/share/fonts/encodings/large
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/100dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/75dpi
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/cyrillic
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/util
Unable to revert mtime: /usr/share/fonts/encodings/large
Unable to revert mtime: /usr/share/fonts/encodings/large
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
0009:fixme:exec:SHELL_execute flags ignored: 0x00000100
Application could not be started, or no application associated with the specified file.
ShellExecuteEx failed: Invalid window handle.

In https://www.playonlinux.com/en/app-1366-Path_of_Exile.html I see that the latest script version if "# Date : 2012-08-16 21-12" (Posted by Deanmsands3 in 2018)

Which one are you using ? what is the Wine version used ?