[aurxenon]

That's very cool. Thanks for the detailed writeup, the journey is the most helpful part of this.

It turned out that FTP was clobbering the figlet binary while it was being uploaded to the Octane

Do you reflexively type BINARY or IMAGE every time you start FTP? Many FTPs default to ASCII and may implement character conversions in that mode.

I normally use FileZilla to upload and download files from the Octane, so I just went and checked my default transfer settings, it appears that FileZilla defaults to treating files without an extension as ASCII files when uploading under FTP. I guess this explains why the object files and the a.out got transferred correctly, but not the figlet executable.