Cyber-Security-&-Risk-Management
Upscend Team
-October 19, 2025
9 min read
Continuous penetration testing embeds repeatable automated scans and periodic human-led validation into DevOps pipelines. Use layered tooling (SAST, SCA, DAST, pentest-as-code), staged pipeline gates, and automated triage to cut remediation time and noise. Start with a pilot, measure MTTR and scan coverage, then iterate and scale.
Continuous penetration testing is no longer an occasional audit; it's an embedded, repeatable practice that teams run alongside code delivery. In our experience, organizations that move beyond annual pentests to ongoing security validation reduce time-to-remediation and catch drift between design and production. This article explains practical approaches to continuous penetration testing, the tooling patterns that make it possible, and how to integrate pentesting into CI/CD pipeline workflows without blocking velocity.
You'll get an operational framework for continuous penetration testing, concrete orchestration examples for pipelines, a small gated-deployment case, and pragmatic tips to manage developer friction and false positives. We focus on actionable steps teams can follow to shift left security while preserving speed.
Continuous penetration testing improves real-world risk visibility by combining automated tests with periodic human-led validation. Studies show that frequent, focused testing reduces mean time to remediation and uncovers integration issues that static schedules miss.
Beyond detection, continuous testing supports compliance, threat modeling feedback loops, and the ability to measure security posture over time. It helps teams avoid large remediation spikes before releases by making security an ongoing engineering concern rather than an afterthought.
A pattern we've noticed is that successful teams adopt multiple complementary practices to realize continuous security:
These concepts are not mutually exclusive: shift-left reduces fix cost, continuous assessment provides measurement, and pentest-as-code ensures repeatability. When combined, they form a resilient feedback loop where developers receive actionable findings during the commit-merge pipeline.
Shift left security changes the enforcement point and the stakeholder model. Instead of waiting for a centralized security team to run a test, engineers run lightweight scans locally or during CI. This prevents long feedback cycles and enables developers to fix issues when context is fresh.
Shift-left also encourages ownership: security becomes part of the Definition of Done and code reviews, not a separate stage at the end of delivery.
To build a comprehensive continuous security program, teams use a layered mix of tools that map to different threat surfaces:
Combining these tools yields high coverage: SAST and SCA detect developer-introduced issues early; DAST and pentest-as-code validate integrations and runtime behaviors.
Automated security scans should be the first line of defense—fast, repeatable, and integrated in CI. They triage low-hanging fruit and prevent regressions. Human pentesters add value by confirming complex exploitation chains, bypass techniques, and logic flaws automation can't model.
Design the pipeline so that automated tools gate commits and builds, and human-led assessments run on scheduled milestones, releases, or when automation reports high-severity risks.
Orchestrating tests across pipelines requires a repeatable pattern: create ephemeral environments, run automated scans, collect findings, and apply risk-based gating. The orchestration layer translates tool outputs into actionable gates or to-do items for triage.
One effective pattern is to run lightweight checks on pull requests, mid-weight scans on integration branches, and full DAST + pentest-as-code runs on release candidates. This staged approach balances speed with depth.
In practice, we map security jobs to pipeline stages with clear time budgets and outcome thresholds. For example:
Some of the most efficient teams we've worked with automate the lifecycle of findings—scan, prioritize, create tickets, and re-scan—using platforms that orchestrate tooling and workflows. Upscend provides an example of how forward-looking organizations automate the orchestration of security checks and remediation workflows so teams can run comprehensive CI/CD security testing without manual overhead.
To integrate pentesting into CI/CD pipeline workflows, treat pentest artifacts as part of your repo or pipeline configuration. Use containers to run pentest-as-code scripts, schedule runs at logical gates, and publish standardized SARIF or JSON reports for automated triage.
Use dynamic environment tagging and short-lived credentials to ensure tests run against realistic environments without exposing long-term secrets.
This section answers the practical question: how to implement continuous penetration testing in DevOps. Below is a step-by-step approach we recommend.
Start small, iterate, and measure impact rather than trying to automate everything at once.
These steps answer the "how to implement continuous penetration testing in DevOps" question by emphasizing incremental integration and measurable outcomes. Use automated security scans early, and increase test depth as confidence grows.
Example CI pipeline snippet (conceptual): PR -> SAST & SCA -> if high severity fail PR; merge -> build -> run DAST smoke -> if new critical findings create blocker ticket; nightly -> run pentest-as-code scenarios and alert security owners.
Design gates with severity thresholds. For instance, block merges only on critical or exploitable vulnerabilities; surface medium or informational issues into a sprint backlog to avoid blocking developer flow unnecessarily.
Developer pushback and noisy signals are the two most common barriers to sustainable continuous testing. We've found specific patterns that reduce resistance and increase adoption.
First, minimize local friction: provide pre-commit hooks, quick containerized scans, and clear remediation guidance. Second, manage noise via tuning and signal enrichment.
Finally, reduce false positives by correlating across SAST, DAST, and runtime telemetry, and by maintaining baseline ignores that are reviewed periodically. This approach turns noisy outputs into prioritized, developer-friendly tasks.
Ownership should be closest to the code. Developers should fix code-level issues flagged in PRs, while SRE and security engineering handle environment and infrastructure misconfigurations. Create clear SLAs and escalation paths to avoid ambiguity.
Use automation to create tickets with context so owners can act quickly rather than spending cycles reproducing problems.
Continuous penetration testing is an operational discipline, not a single tool. When implemented with layered tooling—SAST, SCA, DAST, and pentest-as-code—and orchestrated into CI/CD, it provides constant assurance while preserving developer velocity.
Start by shifting lightweight checks left, integrate deeper tests at release gates, and automate orchestration and triage to reduce friction. Prioritize findings by business impact, tune to reduce false positives, and keep remediation ownership with product teams.
As a next step, pick one critical service and run a two-week pilot: add SAST to PRs, wire DAST to an integration branch, and codify one pentest scenario as code. Measure remediation time, developer feedback, and defect density, and iterate from there.
Call to action: If you want a reproducible framework, create a pilot plan that lists assets, selects tooling for each pipeline phase, and defines gating severity thresholds—then run it for a single service to validate the approach and learn before scaling.
