@costinel: have you made sure you manually set that option to 'true'? It's 'false' by default. For the record, this is what it looks like with a completely fresh vagrant VM for Ubuntu Precise. vagrant@vagrant-ubuntu-precise-64:~$ sudo unattended-upgrade --debug Initial blacklisted packages: Starting unattended upgrades script Allowed origins are: ['o=Ubuntu,a=precise-security'] adjusting candidate version: '' Checking: ca-certificates (["", ""]) Checking: cpio (["", ""]) Checking: libc-bin (["", ""]) Checking: libc-dev-bin (["", ""]) Checking: libc6 (["", ""]) Checking: libc6-dev (["", ""]) Checking: libgcrypt11 (["", ""]) Checking: libgnutls26 (["", ""]) Checking: libssl1.0.0 (["", ""]) Checking: linux-headers-generic (["", ""]) Checking: linux-headers-virtual (["", ""]) Checking: linux-image-virtual (["", ""]) Checking: linux-libc-dev (["", ""]) Checking: linux-virtual (["", ""]) Checking: multiarch-support (["", ""]) Checking: openssl (["", ""]) Checking: perl (["", ""]) Checking: perl-base (["", ""]) Checking: perl-modules (["", ""]) pkgs that look like they should be upgraded: ca-certificates cpio libc-bin libc-dev-bin libc6 libc6-dev libgcrypt11 libgnutls26 libssl1.0.0 linux-headers-generic linux-headers-virtual linux-image-virtual linux-libc-dev linux-virtual multiarch-support openssl perl perl-base perl-modules Fetched 0 B in 0s (0 B/s) check_conffile_prompt('/var/cache/apt/archives/perl_5.14.2-6ubuntu2.5_amd64.deb') found pkg: perl check_conffile_prompt('/var/cache/apt/archives/perl-base_5.14.2-6ubuntu2.5_amd64.deb') found pkg: perl-base check_conffile_prompt('/var/cache/apt/archives/perl-modules_5.14.2-6ubuntu2.5_all.deb') found pkg: perl-modules conffile line: /etc/perl/Net/libnet.cfg fb2946cae573b8ed3d654a180d458733 current md5: fb2946cae573b8ed3d654a180d458733 check_conffile_prompt('/var/cache/apt/archives/libc-dev-bin_2.15-0ubuntu10.13_amd64.deb') found pkg: libc-dev-bin check_conffile_prompt('/var/cache/apt/archives/libc6-dev_2.15-0ubuntu10.13_amd64.deb') found pkg: libc6-dev check_conffile_prompt('/var/cache/apt/archives/libc-bin_2.15-0ubuntu10.13_amd64.deb') found pkg: libc-bin conffile line: /etc/gai.conf 629c0e2f8276b26c29b95f7ed53074d7 current md5: 629c0e2f8276b26c29b95f7ed53074d7 conffile line: /etc/default/nss d6d5d6f621fb3ead2548076ce81e309c current md5: d6d5d6f621fb3ead2548076ce81e309c conffile line: /etc/ld.so.conf.d/libc.conf d4d833fd095fb7b90e1bb4a547f16de6 current md5: d4d833fd095fb7b90e1bb4a547f16de6 conffile line: /etc/bindresvport.blacklist d2d1b996add35b65f64a22e9c8413632 current md5: d2d1b996add35b65f64a22e9c8413632 check_conffile_prompt('/var/cache/apt/archives/libc6_2.15-0ubuntu10.13_amd64.deb') found pkg: libc6 conffile line: /etc/ld.so.conf.d/x86_64-linux-gnu.conf 593ad12389ab2b6f952e7ede67b8fbbf current md5: 593ad12389ab2b6f952e7ede67b8fbbf check_conffile_prompt('/var/cache/apt/archives/linux-libc-dev_3.2.0-99.139_amd64.deb') found pkg: linux-libc-dev check_conffile_prompt('/var/cache/apt/archives/libssl1.0.0_1.0.1-4ubuntu5.35_amd64.deb') found pkg: libssl1.0.0 check_conffile_prompt('/var/cache/apt/archives/libgcrypt11_1.5.0-3ubuntu0.5_amd64.deb') found pkg: libgcrypt11 check_conffile_prompt('/var/cache/apt/archives/libgnutls26_2.12.14-5ubuntu3.12_amd64.deb') found pkg: libgnutls26 check_conffile_prompt('/var/cache/apt/archives/linux-image-3.2.0-99-virtual_3.2.0-99.139_amd64.deb') check_conffile_prompt('/var/cache/apt/archives/multiarch-support_2.15-0ubuntu10.13_amd64.deb') found pkg: multiarch-support check_conffile_prompt('/var/cache/apt/archives/cpio_2.11-7ubuntu3.2_amd64.deb') found pkg: cpio check_conffile_prompt('/var/cache/apt/archives/openssl_1.0.1-4ubuntu5.35_amd64.deb') found pkg: openssl conffile line: /etc/ssl/openssl.cnf ce31ab5015842bf7c2939514a634e0e4 current md5: ce31ab5015842bf7c2939514a634e0e4 check_conffile_prompt('/var/cache/apt/archives/ca-certificates_20160104ubuntu0.12.04.1_all.deb') found pkg: ca-certificates check_conffile_prompt('/var/cache/apt/archives/linux-headers-3.2.0-99_3.2.0-99.139_all.deb') check_conffile_prompt('/var/cache/apt/archives/linux-headers-3.2.0-99-generic_3.2.0-99.139_amd64.deb') check_conffile_prompt('/var/cache/apt/archives/linux-headers-3.2.0-99-virtual_3.2.0-99.139_amd64.deb') check_conffile_prompt('/var/cache/apt/archives/linux-headers-generic_3.2.0.99.115_amd64.deb') found pkg: linux-headers-generic check_conffile_prompt('/var/cache/apt/archives/linux-virtual_3.2.0.99.115_amd64.deb') found pkg: linux-virtual check_conffile_prompt('/var/cache/apt/archives/linux-image-virtual_3.2.0.99.115_amd64.deb') found pkg: linux-image-virtual check_conffile_prompt('/var/cache/apt/archives/linux-headers-virtual_3.2.0.99.115_amd64.deb') found pkg: linux-headers-virtual blacklist: [] InstCount=23 DelCount=0 BrokenCout=0 Packages that are upgraded: ca-certificates cpio libc-bin libc-dev-bin libc6 libc6-dev libgcrypt11 libgnutls26 libssl1.0.0 linux-headers-generic linux-headers-virtual linux-image-virtual linux-libc-dev linux-virtual multiarch-support openssl perl perl-base perl-modules Writing dpkg log to '/var/log/unattended-upgrades/unattended-upgrades-dpkg_2016-03-03_14:13:56.579920.log' adjusting candidate version: '' marking linux-headers-3.2.0-98-generic for remove Packages that are auto removed: 'linux-headers-3.2.0-98-generic' (Reading database ... 97350 files and directories currently installed.) Removing linux-headers-3.2.0-98-generic ... dpkg: warning: while removing linux-headers-3.2.0-98-generic, directory '/lib/modules/3.2.0-98-generic' not empty so not removed. Packages auto-removed InstCount=0 DelCount=1 BrokenCount=0