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I am trying to create chroot user but i want to give him a permissions to create and delete files and directories. I have Ubuntu server installed on virtualbox and i am connecting to it from my host machine Windows 7 using WinSCP. And i am also connecting to Ubuntu server with Cygwin through ssh. These are the permissions for the home directory of the chroot user which is "sites":

root@ubuntu:/var/www# ls -l total 12 -rw-r--r-- 1 root root 177 2015-02-06 20:57 index.html -rw-r--r-- 1 root root 20 2015-02-07 18:04 index.php drwxr-xr-x 3 root root 4096 2015-02-08 22:23 sites

With this settings i am able to connect to the server with the chroot user account but it doesn't allow my to create or delete files. I tried to change the permissions to bob:root and bob:sftponly but then i can't connect to the server. "bob" is the chroot user and "sftponly" is his group.

I am also not able to connect through sftp using Cygwin which is strange because i am able to connect using WinSCP.

And these are the settings from sshd_config

Subsystem sftp internal-sftp

Match Group sftponly
ChrootDirectory %h
ForceCommand internal-sftp
AllowTcpForwarding no
X11Forwarding no

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I found what was the problem. I had to change the custom home directory for user bob which was /var/www/sites to /var/www/. Then give root:root permissions for www directory and bob:sftponly permissions for sites directory. Now i can login with the chrooted user and write in sites directory but not in the www directory which i guess is the normal way how it should work.

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