Decision tree

Which Pentest to Choose and How to Prepare

What exactly do you need to test? Black box tests external access, grey box tests logged-in features, and white box adds code review.

8 pages · PDF · English
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Which Pentest to Choose and How to PreparePDF · 8 pages

Start with one check

Identify the risk you want to test

Read the brief. Is it clear what needs testing: external access, other users' data, user permissions or code flaws?

→ Name the specific risk and use the decision guide to choose an approach.

This is a first step, not a replacement for all the checks.

What to check

Select a check to see the instructions: what good looks like, how to check, the red flag and what to do.

01Identify the risk you want to testIdentify the risk and choose an approach.
What good looks like

The owner identified the risk, and the technical lead included it in the test brief.

How to check

Read the brief. Is it clear what needs testing: external access, other users' data, user permissions or code flaws?

Red flag

The brief only says 'check the website for vulnerabilities'.

What to do

Name the specific risk and use the decision guide to choose an approach.

02List the systems and features to testList the addresses and features to test.
What good looks like

The technical lead has listed the system addresses and features the pentester needs to test.

How to check

Compare the brief with the application. Does it cover the customer portal, payments, admin pages and data exchange between systems?

Red flag

The brief only includes the homepage address.

What to do

Add the required addresses and features. Agree on the list with the provider.

03Create separate test accountsPrepare two customer accounts and other roles.
What good looks like

The technical lead has prepared two independent customer accounts and accounts for other required roles.

How to check

Log in to each account. Check that the two customers have different test data and all required roles are available.

Red flag

There is only one customer account. Access between customers cannot be compared.

What to do

Create the missing accounts. Check logins and test data.

04Document who can do whatDocument who can view and change what.
What good looks like

The technical lead has documented which data each user role can view and change.

How to check

Read the permissions guide. Is it clear who can view invoices, change payments and manage other users?

Red flag

Nobody knows who is allowed to see other customers' invoices.

What to do

List the permitted actions for each role. Share this with the provider.

05Share materials and agree on the rulesAgree on rules and share required materials.
What good looks like

The provider received required materials. Both sides agreed on boundaries, restrictions, contacts and secure access sharing.

How to check

Compare the materials with the brief. Are prohibited actions, the main contact and a secure way to share access defined?

Red flag

The provider does not know the restrictions or has no contact person.

What to do

Agree on restrictions and a contact person. Share access securely.

Choose the format for your task

To read on screen

The main PDF: explanations, checks and actions for every item.

8 pages · PDF · 834 KBDownload PDF

A4 team sheet

One sheet: daily checks, a 30-working-day tracker and contacts.

1 page · PDF · A4 · 400 KBDownload A4 sheet

To print

A light version of the full document for working on paper.

Full document · PDF · 788 KBDownload print version

30-day rollout plan

Use the document as the basis for your rules. Tick the checks for 30 working days until they become a habit.

  1. Week 1Agree the rules

    The owner or manager decides which checks are mandatory and who owns them.

  2. Week 2Assign roles

    Who performs a check and who confirms it. Where possible, two different people.

  3. Week 3Put the sheet up

    Print the A4 sheet and keep it where the process happens.

  4. Week 4Track it

    Tick the checks daily, record exceptions and refine the rules when needed.

After 30 days you have an agreed rule, owners and a record of checks. Not a guarantee of security, a working practice.

Not sure these checks work in your company?

We can independently test whether these controls work in practice, not only on paper.

Discuss an assessment

Help your team avoid costly mistakes

Share these checks with colleagues or download the A4 sheet for everyday use.

Vlad Kraevsky
Prepared by
Vlad Kraevsky
Founder of Veiltrack · penetration tester · GPEN · GWAPT

Penetration testing specialist. Helps companies find vulnerabilities in web applications, APIs and infrastructure and decide which risks to fix first.

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This guide contains general recommendations. The controls available to you depend on your company and the services you use.

Important notes