I still don't get why your example fails.  Does this also happen in a
fresh wineprefix?


Additionally for the "fails silently" issue:  windows that popup in case of an 
error should only be shown if wine was not started from a terminal.  There 
error output is expected in the terminal itself.  What might be a solution is 
to invent a new option "--gui".  This could be added to the Exec line in the 
.desktop file, and would tell Wine to popup windows in case of an "usual" 
error.  Note that crashes of Wine already result in opening a window.

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https://bugs.launchpad.net/bugs/1658884

Title:
  Wine fails *silently* if running programs from nautilus fails

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