error
No such file or directory -
script/../config/../public/images/144/middle/cfa9a31932bea2904485b56294764a6b.jpg
The snippet you posted works, assuming the wrapping is introduced by
the post software.
Could there be a typo that is causing the 'if' to be treated as the end
of a previous statement? This would also require a 'begin' to match
the 'end'...
Looks ok to me. But to avoid spelling errors I'd store the name in a
variable like
f = File.join RAILS_ROOT, "public", "images", property.id, "middle", image.name
File.unlink f if File.exists? f