I read this question about digital signatures and FCC prohibitions on "obscuring" messages in amateur transmissions, and it cause me to think of something: the difference between encryption and compression is small.
If I send a file in compressed form via digital radio (say, a Mesh running on firmware-modified wifi routers, to support data rates that don't make this silly), the contents are easily decompressed by anyone who receives the file in error-free form (and most compression systems include redundant error correction codes to reduce the likelihood that the file will fail decompression) -- but without attempting decompression, there's no simple way to tell whether the file is encrypted within the compressed archive.
It would obviously be a no-no to send an encrypted archive by amateur radio, I think, but where is the line drawn? Does compression itself count as "obscuring" the contents?