Hi, I've a few machines where I'm running Squeeze as guests and ever since the upgrade to Squeeze or fresh installation of it, sudo does not work as expected: I always have to enter the password. Every time. If you don't mind, I've added a more detailed explanation over at serverfault.com . I see this problem on machines with older Debian Lenny machines as well as Squeeze on the host system too: Versions: Kernel: 2.6.32-5-vserver-686 VS-API: 0x00020305 util-vserver: 0.30.215; Jun 18 2010, 15:28:40 Features: CC: gcc, gcc (Debian 4.4.4-5) 4.4.4 CXX: g++, g++ (Debian 4.4.4-5) 4.4.4 CPPFLAGS: '' CFLAGS: '-Wall -g -O2 -std=c99 -Wall -pedantic -W -funit-at-a-time' CXXFLAGS: '-g -O2 -ansi -Wall -pedantic -W -fmessage-length=0 -funit-at-a-time' build/host: i486-pc-linux-gnu/i486-pc-linux-gnu Use dietlibc: yes Build C++ programs: yes Build C99 programs: yes Available APIs: v13,net,v21,v22,v23,netv2 ext2fs Source: e2fsprogs syscall(2) invocation: alternative vserver(2) syscall#: 273/glibc crypto api: nss python bindings: no use library versioning: yes Paths: prefix: /usr sysconf-Directory: /etc cfg-Directory: /etc/vservers initrd-Directory: $(sysconfdir)/init.d pkgstate-Directory: /var/run/vservers vserver-Rootdir: /var/lib/vservers thanks, - Markus [1] http://serverfault.com/questions/406010/sudo-in-debian-squeeze-inside-linux-vserver-always-wants-password