TLDR: I have a user that is a member to a group as a secondary group. This user can delete files with 664 perms as a secondary user, but not directories with perms of 775.

Details: I have a user. Lets call him ftpuser. I use him to upload and download files to my devbox. The user's primary group is "ftp" and is also in the group "www" as a secondary group. My web server runs as user www and group www, and I have proftpd (running as www and www) configured to drop all files into the needed directories as www and www (for file ownership) and perms 664 on files and 775 on directories.

My problem is (tried with 2 ftp clients) the ftp client can delete the files, but not the folders. Filezilla returns 550 permission denied. The owner only can delete flag is not set, and I've triple checked the permissions and they are indeed 775.

Its driving me nuts to have to log into my server to manually delete folders every time. Some of the folders and files are created by 1 of my php scripts, but the permissions are getting set properly when I check the files' properties.

Directory and file creation works phenomenal. Can delete files, just not directories.

Freebsd 9.0 Running in VirtualBox (32bit all the way around) Proftpd (running as www and www) as ftp server (tried using both dreamweaver and filezilla as the clients) Basic amp setup (apache,mysql,and php).