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Manual Enumeration

  1. OS Version: Knowing the distribution (Ubuntu, Debian, FreeBSD, Fedora, SUSE, Red Hat, CentOS, etc.) will give you an idea of the types of tools that may be available. This would also identify the operating system version, for which there may be public exploits available.

  2. Kernel Version: As with the OS version, there may be public exploits that target a vulnerability in a specific kernel version. Kernel exploits can cause system instability or even a complete crash. Be careful running these against any production system, and make sure you fully understand the exploit and possible ramifications before running one.

  3. Running Services: Knowing what services are running on the host is important, especially those running as root. A misconfigured or vulnerable service running as root can be an easy win for privilege escalation. Flaws have been discovered in many common services such as Nagios, Exim, Samba, ProFTPd, etc. Public exploit PoCs exist for many of them, such as CVE-2016-9566, a local privilege escalation flaw in Nagios Core < 4.2.4.

Attacker@xxx[/xxx]$ ps aux | grep root

root         1  1.3  0.1  37656  5664 ?        Ss   23:26   0:01 /sbin/init
root         2  0.0  0.0      0     0 ?        S    23:26   0:00 [kthreadd]
root         3  0.0  0.0      0     0 ?        S    23:26   0:00 [ksoftirqd/0]
root         4  0.0  0.0      0     0 ?        S    23:26   0:00 [kworker/0:0]
root         5  0.0  0.0      0     0 ?        S<   23:26   0:00 [kworker/0:0H]
root         6  0.0  0.0      0     0 ?        S    23:26   0:00 [kworker/u8:0]
root         7  0.0  0.0      0     0 ?        S    23:26   0:00 [rcu_sched]
root         8  0.0  0.0      0     0 ?        S    23:26   0:00 [rcu_bh]
root         9  0.0  0.0      0     0 ?        S    23:26   0:00 [migration/0]

<SNIP>
  1. Installed Packages and Versions: Like running services, it is important to check for any out-of-date or vulnerable packages that may be easily leveraged for privilege escalation. An example is Screen, which is a common terminal multiplexer (similar to tmux). It allows you to start a session and open many windows or virtual terminals instead of opening multiple terminal sessions. Screen version 4.05.00 suffers from a privilege escalation vulnerability that can be easily leveraged to escalate privileges.

  2. Logged in Users: Knowing which other users are logged into the system and what they are doing can give greater into possible local lateral movement and privilege escalation paths.

Attacker@xxx[/xxx]$ ps au

USER       		PID %CPU %MEM    VSZ   RSS TTY      STAT START   TIME COMMAND
root      		1256  0.0  0.1  65832  3364 tty1     Ss   23:26   0:00 /bin/login --
cliff.moore     1322  0.0  0.1  22600  5160 tty1     S    23:26   0:00 -bash
shared     		1367  0.0  0.1  22568  5116 pts/0    Ss   23:27   0:00 -bash
root      		1384  0.0  0.1  52700  3812 tty1     S    23:29   0:00 sudo su
root      		1385  0.0  0.1  52284  3448 tty1     S    23:29   0:00 su
root      		1386  0.0  0.1  21224  3764 tty1     S+   23:29   0:00 bash
shared     		1397  0.0  0.1  37364  3428 pts/0    R+   23:30   0:00 ps au
  1. User Home Directories: Are other user's home directories accessible? User home folders may also contain SSH keys that can be used to access other systems or scripts and configuration files containing credentials. It is not uncommon to find files containing credentials that can be leveraged to access other systems or even gain entry into the Active Directory environment.
Attacker@xxx[/xxx]$ ls /home

backupsvc  bob.jones  cliff.moore  logger  mrb3n  shared  stacey.jenkins
  1. Sudo Privileges: Can the user run any commands either as another user or as root? If you do not have credentials for the user, it may not be possible to leverage sudo permissions. However, often sudoer entries include NOPASSWD, meaning that the user can run the specified command without being prompted for a password. Not all commands, even we can run as root, will lead to privilege escalation. It is not uncommon to gain access as a user with full sudo privileges, meaning they can run any command as root. Issuing a simple sudo su command will immediately give you a root session.
Attacker@xxx[/xxx]$ sudo -l

Matching Defaults entries for sysadm on NIX02:
    env_reset, mail_badpass, secure_path=/usr/local/sbin\:/usr/local/bin\:/usr/sbin\:/usr/bin\:/sbin\:/bin\:/snap/bin

User sysadm may run the following commands on NIX02:
    (root) NOPASSWD: /usr/sbin/tcpdump
  1. Configuration Files: Configuration files can hold a wealth of information. It is worth searching through all files that end in extensions such as .conf and .config, for usernames, passwords, and other secrets.

  2. Readable Shadow File: If the shadow file is readable, you will be able to gather password hashes for all users who have a password set. While this does not guarantee further access, these hashes can be subjected to an offline brute-force attack to recover the cleartext password.

  3. Password Hashes in /etc/passwd: Occasionally, you will see password hashes directly in the /etc/passwd file. This file is readable by all users, and as with hashes in the shadow file, these can be subjected to an offline password cracking attack. This configuration, while not common, can sometimes be seen on embedded devices and routers.

Attacker@xxx[/xxx]$ cat /etc/passwd

root:x:0:0:root:/root:/bin/bash
daemon:x:1:1:daemon:/usr/sbin:/usr/sbin/nologin
bin:x:2:2:bin:/bin:/usr/sbin/nologin
sys:x:3:3:sys:/dev:/usr/sbin/nologin
sync:x:4:65534:sync:/bin:/bin/sync
games:x:5:60:games:/usr/games:/usr/sbin/nologin
man:x:6:12:man:/var/cache/man:/usr/sbin/nologin
lp:x:7:7:lp:/var/spool/lpd:/usr/sbin/nologin
mail:x:8:8:mail:/var/mail:/usr/sbin/nologin
news:x:9:9:news:/var/spool/news:/usr/sbin/nologin
<...SNIP...>
dnsmasq:x:109:65534:dnsmasq,,,:/var/lib/misc:/bin/false
sshd:x:110:65534::/var/run/sshd:/usr/sbin/nologin
mrb3n:x:1000:1000:mrb3n,,,:/home/mrb3n:/bin/bash
colord:x:111:118:colord colour management daemon,,,:/var/lib/colord:/bin/false
backupsvc:x:1001:1001::/home/backupsvc:
bob.jones:x:1002:1002::/home/bob.jones:
cliff.moore:x:1003:1003::/home/cliff.moore:
logger:x:1004:1004::/home/logger:
shared:x:1005:1005::/home/shared:
stacey.jenkins:x:1006:1006::/home/stacey.jenkins:
sysadm:$6$vdH7vuQIv6anIBWg$Ysk.UZzI7WxYUBYt8WRIWF0EzWlksOElDE0HLYinee38QI1A.0HW7WZCrUhZ9wwDz13bPpkTjNuRoUGYhwFE11:1007:1007::/home/sysadm:
  1. Cron Jobs: Cron jobs on Linux systems are similar to Windows scheduled tasks. They are often set up to perform maintenance and backup tasks. In conjunction with other misconfigurations such as relative paths or weak permissions, they can leverage to escalate privileges when the scheduled cron job runs.
Attacker@xxx[/xxx]$ ls -la /etc/cron.daily/

total 60
drwxr-xr-x  2 root root 4096 Aug 30 23:49 .
drwxr-xr-x 93 root root 4096 Aug 30 23:47 ..
-rwxr-xr-x  1 root root  376 Mar 31  2016 apport
-rwxr-xr-x  1 root root 1474 Sep 26  2017 apt-compat
-rwx--x--x  1 root root  379 Aug 30 23:49 backup
-rwxr-xr-x  1 root root  355 May 22  2012 bsdmainutils
-rwxr-xr-x  1 root root 1597 Nov 27  2015 dpkg
-rwxr-xr-x  1 root root  372 May  6  2015 logrotate
-rwxr-xr-x  1 root root 1293 Nov  6  2015 man-db
-rwxr-xr-x  1 root root  539 Jul 16  2014 mdadm
-rwxr-xr-x  1 root root  435 Nov 18  2014 mlocate
-rwxr-xr-x  1 root root  249 Nov 12  2015 passwd
-rw-r--r--  1 root root  102 Apr  5  2016 .placeholder
-rwxr-xr-x  1 root root 3449 Feb 26  2016 popularity-contest
-rwxr-xr-x  1 root root  214 May 24  2016 update-notifier-common
  1. Unmounted File Systems and Additional Drives: If you discover and can mount an additional drive or unmounted file system, you may find sensitive files, passwords, or backups that can be leveraged to escalate privileges.
Attacker@xxx[/xxx]$ lsblk

NAME   MAJ:MIN RM  SIZE RO TYPE MOUNTPOINT
sda      8:0    0   30G  0 disk 
├─sda1   8:1    0   29G  0 part /
├─sda2   8:2    0    1K  0 part 
└─sda5   8:5    0  975M  0 part [SWAP]
sr0     11:0    1  848M  0 rom  
  1. SETUID and SETGID Permissions: Binaries are set with these permissions to allow a user to run a command as root, without having to grant root-level access to the user. Many binaries contain functionality that can be exploited to get a root shell.

  2. Writeable Directories: It is important to discover which directories are writeable if you need to download tools to the system. You may discover a writeable directory where a cron job places files, which provides an idea of how often the cron job runs and could be used to elevate privileges if the script that the cron job runs is also writeable.

Attacker@xxx[/xxx]$ find / -path /proc -prune -o -type d -perm -o+w 2>/dev/null

/dmz-backups
/tmp
/tmp/VMwareDnD
/tmp/.XIM-unix
/tmp/.Test-unix
/tmp/.X11-unix
/tmp/systemd-private-8a2c51fcbad240d09578916b47b0bb17-systemd-timesyncd.service-TIecv0/tmp
/tmp/.font-unix
/tmp/.ICE-unix
/proc
/dev/mqueue
/dev/shm
/var/tmp
/var/tmp/systemd-private-8a2c51fcbad240d09578916b47b0bb17-systemd-timesyncd.service-hm6Qdl/tmp
/var/crash
/run/lock
  1. Writeable Files: Are any scripts or configuration files world-writable? While altering configuration files can be extremely destructive, there may be instances where a minor modification can open up further access. Also, any scripts that are run as root using cron jobs can be modified slightly to append a command.
Attacker@xxx[/xxx]$ find / -path /proc -prune -o -type f -perm -o+w 2>/dev/null

/etc/cron.daily/backup
/dmz-backups/backup.sh
/proc
/sys/fs/cgroup/memory/init.scope/cgroup.event_control

<SNIP>

/home/backupsvc/backup.sh

<SNIP>