Take an undocumented executable of unknown origin. Trying /?, -h, --help from the command line yields nothing. Is it possible to discover if the executable supports any command line options by looking inside the executable? Possibly reverse engineering? What would be the best way of doing this?
I'm talking about a Windows executable, but would be interested to hear what different approaches would be needed with another OS.
If it's a .NET executable try using Reflector. This will convert the MSIL code into the equivalent C# code which may make it easier to understand. Unfortunately private and local variable names will be lost, as these are not stored in the MSIL but it should still be possible to follow what's going on.
In linux, step one would be run strings your_file which dumps all the strings of printable characters in the file. Any constants chars will thus be shown, including any "usage" instructions.
Next step could be to run ltrace on the file. This shows all function calls the program does. If it includes getopt (or familiar), then it is a sure sign that it is processing input parameters. In fact, you should be able to see exactly what argument the program is expecting since that is the third parameter to the getopt function.
For Windows, you can see this question about decompiling Windows executables. It should be relatively easy to at least discover the options (what they actually do is a different story).