As for testing your executable, I'd recommend opening a command prompt and try running it from there. It's possible that by doing so, you may get to see any output that gets sent to STDERR. Otherwise, things may disappear before you get a chance to see them.

Looking at how you're using pp, I suspect that may be the root of your issues. Look at the documentation for pp for more details about the available options. In particular, I'd recommend using -c and/or -x options. (NOTE: That's -c and -x, not -C and -X.) These options will try to "determine additonal run-time dependencies" and will package those into your executable. If you find out that you're still missing packages/libraries/files, you may need to use other options to explicitly add in those packages/libraries/files.