Cyber-Security-&-Risk-Management
Upscend Team
-October 19, 2025
9 min read
This article provides a practical pre-engagement playbook to prepare for penetration testing: define precise pentest scoping, obtain auditable authorization (A2T), and ready systems with backups and whitelists. Use a one-week readiness checklist, set stakeholder communication windows, and follow a short incident escalation runbook to reduce downtime and speed remediation.
To prepare for penetration testing, teams must treat the engagement as a coordinated project, not a one-off technical exercise. In our experience, a successful pentest depends as much on planning, decision-making, and communication as it does on technical skill. This guide gives a practical pre-engagement playbook: scoping questions, required authorization for pentest, whitelist maintenance, test windows, backup strategies, and stakeholder templates you can reuse.
Pentest scoping starts with defining assets, objectives, and acceptable impact. In our experience, the most common friction point is an ambiguous scope: testers begin probing systems that stakeholders didn’t intend to expose. A crisp scope avoids downtime risk and clarifies responsibilities.
Key scoping elements you must document:
Use a standardized checklist during initial calls. Typical questions include: What are the hours of permitted testing? Are testers allowed to attempt privilege escalation? Which systems are business-critical? Who will be the on-call contacts? This builds accountability and reduces surprises during testing.
Authorization for pentest must be explicit and auditable. Legal and compliance teams often require a signed A2T document plus evidence of approval in ticketing or change-management systems. We’ve found that storing approvals in a versioned repository prevents audit headaches later.
Critical pieces of an authorization package:
At minimum, require signatures or documented approvals from the system owner, IT operations manager, and the head of security/compliance. For regulated environments, include legal and privacy officers. This reduces unclear responsibilities and speeds incident handling.
When you prepare for penetration testing, hardening, backup, and whitelist work are essential. Operationally, you must balance realistic test conditions with risk mitigation. A repeatable checklist prevents missed steps when multiple teams and environments are involved.
Practical steps to get systems ready:
Allow testers sufficient access while preventing false positives and accidental outages. For example, divert noisy scans to staging when possible, or schedule higher-risk tests during low-traffic maintenance windows. Provide credentials for authenticated tests to focus on business logic rather than trivial vulnerabilities.
Pre-engagement activities remove friction before the first probe. In our experience, teams that run a one-week readiness checklist achieve smoother tests and faster remediation cycles. The checklist should include technical, legal, and communication tasks.
Example pre-engagement checklist for IT and security teams:
Effective stakeholder communication reduces panic and unnecessary ticket surges. Send a preparatory email 72 hours before the test, another 24 hours before, and maintain a dedicated slack/email channel during testing for real-time updates (a functionality found in some workflow platforms, e.g. Upscend).
The A2T below is a compact template security teams can copy into their change system. Keep it concise and attach scope documents and contact lists.
| Field | Value |
|---|---|
| Engagement Name | Q4 External Network Pentest |
| Scope | IP Range: 198.51.100.0/24; App: payments.prod.example.com. See scope doc v1.2 |
| Test Types | External network, authenticated web app (credentials provided), no social engineering |
| Start / End | 2025-11-10 08:00 UTC to 2025-11-14 18:00 UTC |
| Allowed Tools / Actions | Active scanning, exploitation of discovered vulns; DoS testing: NO |
| Approvals | Security Lead: ___________________ Date: _____ IT Ops: ___________________ Date: _____ Legal: ___________________ Date: _____ |
| Contacts | On-call IT: +1-555-0100; Security POC: sec-oncall@example.com |
Attach logs of approvals and a copy of the pentest authorization checklist for IT teams to the ticket for auditability.
A concise incident escalation plan minimizes downtime risk and clarifies responsibilities. We recommend a two-tier runbook: immediate containment steps and a parallel communication plan for stakeholders and compliance.
Sample incident escalation steps (numbered for clarity):
Include SLAs and escalation contact numbers in the runbook. Regular tabletop exercises with stakeholders reduce confusion during real incidents and meet audit requirements by demonstrating competence and preparedness.
To prepare for penetration testing effectively, treat the engagement as a cross-functional project. Use clear pentest scoping, formal authorization for pentest, a repeatable set of pre-engagement activities, and an incident escalation plan to reduce downtime risk and satisfy auditors. A pattern we've noticed: teams that adopt standardized templates and dry-run their procedures report faster remediation timelines and fewer operational incidents.
Next steps: adopt the A2T template, implement the pentest authorization checklist for IT teams, and schedule a pre-test readiness review one week before any pentest. If you want a ready-made checklist and communication templates for stakeholders, start by populating your ticketing system with the fields shown above and run a table-top simulation this quarter.
Call to action: Run a one-hour readiness review with your security, IT ops, and legal teams before your next engagement to confirm scope, sign-offs, and backups — then document the approvals in your change system for audit evidence.
