https://bugs.winehq.org/show_bug.cgi?id=42735
--- Comment #12 from Jeremy Newman jnewman@codeweavers.com --- We use inotifywait to watch the directory and when a file is updated, it requests a purge of the CDN for that file. Unfortunately, inotifywait DOES not transverse symbolic links, so it will not request a purge of anything in that dir.
We could possibly hack the script, and add a manual list of directories that are known symbolic links, but then it would need to be updated every time there is a new release of Debian/Ubuntu.
I'm open to suggestions, but all I can think of currently is for you to not use symbolic links and make full copies of the structure.