I tried sending another picture recently, and I again experienced the same thing. Not working initially, then working when starting from ssh. I am experiencing a similar situation with Fernschreiber. Fernschreiber however gives an error “can’t get stat about the file” when it doesn’t work.
I now suspect that this is maybe something with my specific setup, something to do with permissions somehow?
I’ve symlinked my pictures folder (and other folders) from my home dir to my sdcard, so that I have a continuous backup. So far this has worked great. However when I go to share a picture in whisperfish and I choose “File system” I can only see my homedir, not the sdcard (I can see it if I start whisperfish from ssh). In the homedir, all folders (like pictures) are 0 byte files (but not when started from ssh).
Could the problem be that whisperfish doesn’t have access to the sdcard, so sharing a file from there would never work? Even though e.g. the image picker does see it?