10 Best Penetration Testing Phases & Lifecycle – A Pentesters Guide 2023

Penetration Testing Phases involves various Methods, phases, lifecycle, and scope to prepare the best checklist to perform quality penetration operations. Here we have created a complete Penetration Testing Guide with detailed step-by-step methods.

Let’s take a look at how you can get better in your pentesting engagements by breaking your methodology into well-defined stages, leading to efficient workflow.

There is no denying that any penetration testing project is a lengthy process, involving a lot of different skills.

Tackling everything at once can not overwhelm pentesters, a lot of mishaps can take place: unexplored targets and assets overlooked vulnerabilities and old dusty findings and a lot more. 

So what’s the better way on fixing such a mess? 

If you try to break down your Penetration Testing Phases & lifecycle into smaller steps, with well-formed objectives and perform them in a sequential manner, it will turn pentest into an efficient and precise process.

Also you can download advanced Penetration Testing As a Service Red Team & Blue Team workspace.

What steps do penetration testing Phases, lifecycle, and Methods consist of?

Penetration Testing phases start with timelines and scoping of targets to the discovery of attack surface up to reporting phase, a lot of things come in between. Careful execution of each step will benefit your team with the help of the best Pentest providers.

Penetration Testing Phases Guide	How to Perfrom?
Scoping	Scoping is crucial, it needs a lot of attention and clarified Pentesting documentation before proceeding ahead.
Scheduling	Scheduling part of the penetration testing Phases and life cycle. Clients and the team decide when to start the project, when to expect the first results, and when to expect the full report.
Reconnaissance	Reconnaissance is a process or method to get information in-depth about the target. Keep gathering information until penetration testing phases get started to go depth to perform in-depth Pentest operation.
Exploitation	The exploitation phase of the goal of the pentest engagement is to get a reverse shell (or pop a shell as red teamers say) from the client’s server to yours.
Escalation	Escalation can be horizontal or vertical. Horizontal escalation involves pivoting to another user with similar privileges while vertical escalation is pivoting to a user with higher privileges.
Persistence	The persistence phase lets you continuously access to the compromised server to go through the whole exploitation process again is cumbersome.
Exfiltration	The exfiltration phase is a method to dump as much sensitive information as possible after gaining the highest possible privilege level. Gather as many password dumps, hashes, PII, etc.
Reporting	Reporting phase required to write well-structured and comprehensive penetration testing reports is an important skill.
Remediation	This can help the customer’s security team in expediting the task of fixing bugs that were pointed out from the penetration testing report and ensure the process continues until all the vulnerabilities got fixed.
Retesting	Once Red Team submits findings through a branded penetration testing report, the Blue team gets on with their task of mitigations: creating Jira tasks, checking the patching progress, and stuff.

Penetration Testing Phases Guide – Lifecycle

• The Beginning: Scoping
• Deadlines are important: Scheduling
• Reconnaissance
• Breaking In: Exploitation
• Root, Admin and Beyond: Escalation
• Leaving Backdoors: Persistence
• Data Gathering: Exfiltration (Post-exploit)
• Efficient Communication: Reporting
• Patching, Mitigations and Updates: Remediation
• The Final Checks: Retesting

Penetration Testing Phase 1. The Beginning: Scoping

Before the penetration testing process begins, the client defines the boundaries and limits of testing.

• IPs
• Domains 
• Subdomains
• Mobile applications (if applicable)

This step is to define the perimeter where you and your team are free to test. Scoping is crucial, it needs a lot of attention and clarified Pentesting documentation before proceeding ahead.

Long story short, there were incidents with pentest teams that started testing on the wrong set of IPs and compromised the servers. We don’t want this to happen with our users.

It’s important to store the scope in the most convenient way to work with sensitive data properly. Many clients usually provide their scope a basic text file that can be imported into Hexway Hive to start working with data immediately. 

Penetration Testing Phase 2. Deadlines are important: Scheduling

Clients want to reduce the time of penetration testing to start working on vulnerabilities faster. The traditional approach can’t provide such an option, that’s why it was painful for both sides. Especially difficulties with allowing remediation as soon as bugs meet the pentester. 

Hexway Hive has such functionality. Penetration testers find vulnerabilities using VAPT Tools and send them to the customer portal. So clients can start working on fixing them in no time to send them back for retesting without waiting for the end of the pentest.

That also relates to the scheduling part of the penetration testing cycle. Clients and the team decide when to start the project, when to expect the first results and when to expect the full report. Pentests also require clients for special arrangements:

• whitelisting testers’ IPs
• temporary accounts
• staying within compliance 
• etc. 

 Scheduling deadlines is important to keep everything tracked and deliver results just in time. Pentesters need to set goals according to the discussed period of the project. 

Penetration Testing Phase 3. Reconnaissance

That is the lengthiest part of the engagement, but no need to panic. It can usually be divided into two common parts:

Mapping The Surface: Discovery

In this Penetration Testing Guide Usually, scope only defines the limits, but not everything inside the scope is an active server or a reachable domain.

Discovery can be seen as the first part of the reconnaissance phase: mapping the attack surface.

This step provides testers with assets to probe further for details. 

Tools like Nmap or Amass play a crucial role at this point. Subdomain uncovering tools like Subfinder, Chaos or others are necessary to discover less-used subdomains, which can tend to be vulnerable.

Further, to confirm that the subdomains are resolving, Massdns is something that can be used. There are multiple tools used in the discovery stage to map as many assets as possible.

In one of our previous materials, we’ve already mentioned tools for each pentest phase. Below are re-mentioned some of them that fit the Discovery phase:

• Nmap: As mentioned earlier, Nmap is one of the most popular port scanners and it’s even equipped with scripts to evaluate IPs for vulnerabilities and exploit standard bugs. 
• Masscan: Fast port scanner to scan a large amount of IP/CIDR ranges.
• Crt.sh: A popular collection of SSL certificates to search through them in order to find exposed subdomains. 
• Maltego: A relational tool to fetch and mine data from various online resources and search engines, mainly used for OSINT and recon.
• Shodan.io: Global search engine to sift through open devices on the internet, ranging from server to IOT devices.
• SubBrute: A tool to brute force DNS enumeration to find rare subdomains. 

Penetration Testing Phase 3: Digging Deeper: Enumeration

In this Penetration Testing Phases Once the assets are ready, it’s time to move on to the next phase of recon: enumerating the valid targets. This is where pentesters find the foothold that can lead to the compromise tea of the vulnerable asset.

Enumeration is widely considered one of the tasks that need the most thorough execution. Better the enumeration, the higher the chances of gaining entry. 

The checklists of enumeration can get huge: 

• fuzzing for hidden directories
• brute-forcing parameters
• looking for JS secrets
• finding valid CVEs 
• and much much more

Ffuf is a great tool to fuzz directories, virtual hosts, API endpoints, etc. Nuclei by Project Discovery is very helpful in finding servers vulnerable to CVEs, standard misconfiguration, and other exploits through the use of templates.

Make sure to keep track of all your finding as it might get difficult to track on larger scopes.

By the way, Hexway also has great functionality to work with Penetration testing checklist and never misses a thing.

It allows users to implement methodologies and track the whole pentest progress wisely. 

Penetration Testing Phase 4. Breaking In: Exploitation

This stage is self-explanatory: it’s time to exploit the vulnerabilities discovered during the recon phase. The exploitation phase of pentest engagements goal is to get a reverse shell (or pop a shell as red teamers say) from the client’s server to yours.

This indicates a successful compromise of the server (depends on the level of permission the hacked user has).

Now the path to getting this shell can be easy as uploading a malicious script and executing it or as difficult as chaining multiple vulnerabilities to writing custom exploits. Everything depends on how hardened the target is.

The majority of the exploitation is a manual task, where analysis of the vulnerability is required to exploit it.

In some cases, standard exploits might be leveraged. Tools like Metasploit, and Armitage can perform automated exploitation.

Ready-to-launch scripts from exploitdb.com and packetstorm.com are also helpful.

Small subsets of vulnerabilities like SQL injection and SSTI can be exploited through sqlmap and plump, respectively.

Carefully examine the intel gathered in the enumeration phase to determine what can be done manually and where automation can ease the process. 

During the exploitation phase, it’s excessively important to keep all information about bugs and vulnerabilities tracked.

Especially when someone from your team wasn’t able to exploit it, for example.

Hexway Hive is a perfect tool for such needs. Anyone can start exploring the bug and keep all the actions in a Note linked to the service/ host or Resolutions.

Someone else on the team can continue his actions without starting from the beginning, which is pretty awesome. This saves a lot of time for pentesters and their clients.

By the way, it’s not the ending point of the process. The team Lead can also help his pentester to create an exploitation plan in checklists with additional instructions on how to perform exploitation successfully.

After the successful exploitation, the same method works for tracking the post-exploitation phase and tracking loot. 

Penetration Testing Phase 5. Root, Admin, and Beyond: Escalation

Most of the time reverse shells are received through the exploitation of a service. This leads to having access to the server with as much permission as the service has, usually granting pentesters with a low-level user role or a service account.

In this Penetration Testing Guide, You are limited by the lesser amount of privileges used by these accounts. That’s where escalating to more powerful accounts comes into play.

Escalation can be horizontal and vertical. Horizontal escalation involves pivoting to another user with similar privileges while vertical escalation is pivoting to a user with higher privileges.

In Active Directory (AD) environments, Domain Controller or Domain Admin is the user with the highest privileges. In Unix/Linux environments, that user is the root.

Again a manual process, but you can aid it by using scripts that can report standard misconfigurations.

linPEAS (or winPEAS for Windows) are popular scripts to search for possible escalation paths to privileges.

Bloodhound is a strong tool that can gather data and reveal paths that can lead to the compromise of the Domain Controller.

Penetration Testing Phase 6. Leaving Backdoors: Persistence

In the Penetration Testing lifecycle, It’s a rare scenario to gather everything you need in one go when you get a reverse shell.

You’ll need continuous access to the compromised server to go through the whole exploitation process again is cumbersome.

That’s where persistence comes into action: leaving a backdoor or an easily accessible script that lets you go in again and again until it’s required.  

Penetration Testing Phase 7. Data Gathering: Exfiltration (Post-exploit)

A this Penetration Testing Phases, One of the main goals of this phase is to dump as much sensitive information as possible after gaining the highest possible privilege level to prove the impact of the breach. Gather as many password dumps, hashes, PII etc. 

Dumping hashes in an Active Directory environment can be done through many PowerShell scripts or tools, one of the most reliable is Mimikatz, which allows you to dump LSASS very easily.

To transfer data you can leverage the HTTP server created on the client’s machine to extract the data.

Chisel is a popular tool to create instant servers in case python is not present in the windows environment. 

At this point there’s one painful headache — where to store all this information?  Speaking of which.

That’s where Hexway also got your back covered. They developed a special section called Credentials. Here you can keep everything you found during the exploitation phase. 

Penetration Testing Phase 8. Efficient Communication: Reporting

In this Penetration Testing Guide, All of the team efforts would be wasted if a client won’t be able to fix exploited findings. Hence, writing well-structured and comprehensive reports is an important skill.

Starting with an executive summary (which explains everything Red Team did in one paragraph), moving on to describing the vulnerabilities, exploitation, etc.

Simply put everything from the above steps that might have an impact on the customer’s business. 

Yet there are a lot of different report generators to simplify this phase. Penetration Testing lifecycle Nevertheless plenty of them are pretty uncomfortable to use, especially open-source ones.

That’s the exact reason why reporting is super painful for pentesters. Hexway Hive developed an internal report generator that collects data from all previous steps and turns it into human-readable data in a customizable docx report. 

Plus Hexway creates custom report templates for free. Welcome to the future, and welcome to Penetration Testing as a service – PTaaS.

Penetration Testing Phase 9. Patching, Mitigations and Updates: Remediation

As mentioned in the previous step, pentest provider should suggest remediation for the found vulnerabilities.

This can help the customer’s security team in expediting the task of fixing bugs from the report.

Suggested mitigations range from standard code practices like input sanitization, prepared statements etc (to protect against injection and other OWASP Top 10 vulnerabilities to upgrading software versions (to protect against popular and known CVEs).

The focus should be on keeping systems patched and up-to-date, which eliminates most of the foothold and entry points for attackers (and Red teamers alike).

Penetration Testing Phase 10. The Final Checks: Retesting

Once Red Team submit findings through a branded report, Blue team gets on with their task of mitigations: creating Jira tasks, checking the patching progress and stuff. This can take a while…

But Hexway solutions even make these faster with smart Jira integration and status change.

When defenders are satisfied with patches, they can reach back toRed Team to get a retest: it’s needed to confirm that previously vulnerable services are now not exploitable. 

The communication and relation between Red Teams and Blue Teams are known as Purple teaming. It’s important that everyone is on the same page.

Blue Team usually shares a document with their needs with the pentesters.

They can use a tool like Hexway Apiary to log the process of patching and share it with fellow pentesters in real-time. 

These 10 stages of a penetration testing guide lifecycle are what almost every security team goes through.

Some may use different names, but the overall concept remains the same. re

Keep them handy and be better than your competition when it comes to pentests! Good luck and start providing PTaaS with Hexway. 

Frequently Asked Questions

What is Penetration Testing?

Penetration testing also known as Pen Test is a simulation of a real-time cyberattack against a computer networks, web applications and any software to find and exploit the vulnerabilities.

The purpose of penetration testing is to assess the security of a system or network and identify any weaknesses that could be exploited by cybercriminals.

What are the 3 Phases of Penetration Testing?

These are 3 Penetration Testing Phases.

1. Planning and reconnaissance

2. Attack and Gaining Access

3. Exploit and Report

What are Phases of Penetration Testing ?

3. Mobile Application Testing

4. Wireless Penetration Testing.

5. Physical Penetration Testing.

6. Internal/External Infrastructure Penetration Testing

7.Social Engineering Penetration Testing.

What are the 10 Best Penetration Testing Tools?

1. Metasploit

2. NMAP

3. Wireshark

4. Aircrack

5. Nessus

6. Social Engineering Toolkit

7. W3AF

8. Burp Suite

9. BeEF

10. SQLmap

What are The Types of Penetration Testing?

1. Blackbox Penetration Testing
2. White Box Penetration Testing

3. Gray Box Penetration Testing

20 Best Penetration Testing Companies?

1. Hexway

2. Intruder.

3. Acunetix

4. Rapid7

5. Cobalt.io.

6. Invicti

7. Indusface WAS

8. SecureWorks

9. Intruder

10.Coalfire Labs

11.ImmuniWeb®

12.Raxis

13.FireEye

14.Astra

15.Netragard

16.QAlified

17.Cipher Security LLC

18.Software Secured

19.Offensive Security

20.Securus Global

What are the 10 Best Penetration Testing Certifications?

CWPT – Certified Web Penetration Tester (Ethical Hackers Academy)
CNPT – Certified Network Penetration Tester (Ethical Hackers Academy)
PenTest+ – CompTIA Pentest+ (CompTIA)
CPENT– Certified Penetration Testing Professional (EC Council)
OSCP – Offensive Security Certified Professional (Offensive Security)
GPEN – GIAC Penetration Tester (SANS)
CPTE – Certified Penetration Testing Engineer (NICCS)
eJPT – eLearn Security Junior Penetration Tester (eLearn Security)
C)PTE–
CPT – Certified Penetration Tester (Pentester Academy)

What is Penetration Testing as a Service?

Penetration testing as a service, also known as PTaaS, is a cloud-based penetration testing solution that enables businesses to conduct regular, automated penetration tests with ease.

PTaaS platforms provide users with all the tools and resources they need to run effective penetration tests, including a web-based interface, an extensive knowledge base, and 24/365 customer support.

How Can You Get a Penetration Testing Quote?

If you want to obtain a penetration testing quote, there are a few things you must do.

1.You need to gather information about your system or network, including its size and complexity

2 You must choose whether you need a comprehensive or basic penetration test

3. You’ll need to contact a number of penetration testing firms and ask for quotations from each one

Why Is Penetration Testing Important?

One of the most important reasons is that it helps to ensure that your systems and networks are secure against potential threats.

Penetration testing can also help you to understand how vulnerable your systems and networks are to attack, and what steps you need to take to improve their security.

By identifying vulnerabilities early on, you can avoid the costly repairs and replacements that would be necessary if your system or network was to be hacked.

Penetration testing is also critical since it may help you boost your brand image and reputation. Customers will be more inclined to trust you with their personal information if your systems and networks are secure

Useful Related InfoSec Resources