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Question 08 · 🛡️ Security testing

How often should you run automated security tests?

Short answerOne possible schedule: a quick check every week and a deep analysis every month.
Illustration for question 8: How often should you run automated security tests?

A security test done just once gets outdated quickly: the code changes, new dependencies are added, and new vulnerabilities appear. A regular cadence makes security routine instead of a surprise.

The answer

A practical cadence is to divide the work into levels: a quick weekly check and a deeper monthly review.

A third level, with much broader and more expensive tests, can happen every quarter. This full assessment still requires a specialist or an advanced tool; in the meantime, a hired specialist can cover this role.

Over time, save the patterns found in each round so the tests become more useful and you don’t have to explain the same approach to the agent every time.

What to include in the weekly check

The quick check should be inexpensive and automatic. It looks for dependencies with known vulnerabilities, passwords or keys left in the code, exposed settings, and unnecessarily open ports. It runs on its own and only alerts someone when it finds something.

An AI agent can summarize the report and separate urgent issues from those that can wait. A person should still review the fix.

What to include in the monthly review

The deeper review looks at the system’s logic. Who can access what? Can one user see another user’s data? Can the login handle repeated attempts? Did the new parts of the code open up a new path? It takes more time, uses more resources, and requires someone to review the results carefully.

Also do one right after major changes instead of waiting until the end of the month.

The full quarterly test

The full assessment tries to chain small vulnerabilities together until they lead to something serious, as an attacker would. Since this level still requires experience and advanced tools, a hired specialist usually covers it. Ask for a report that includes the steps they used so you can automate whatever is possible later.

Memory between rounds

Keep a file with findings, what was fixed, false alarms, and approaches that worked. In the next round, give that file to the agent as context. That way, it won’t repeat approaches that were already ruled out, and it can check whether old vulnerabilities have returned.

Always test only systems you own or have written permission from the owner to test.

An exampleA small software company schedules a dependency and code key scan every Monday, with alerts sent to the team chat. During the first week of the month, an agent reviews the permissions on new routes. Every three months, a specialist runs a full test, and the findings go into the patterns file that the agent reads in later rounds.
The idea in one image
Every weekQuick check
Every monthDeep analysis
Every quarterComprehensive test (specialist or advanced tool)
In practice
  1. List the systems you own or have written permission to test.
  2. Automate the weekly check and send an alert only when it finds something.
  3. Set a fixed date each month for the deeper review.
  4. Plan the quarterly test with a specialist and define the scope in writing.
  5. Record findings, fixes, and false alarms in one file.
  6. Give that file to the agent at the start of each round.
Common mistakes
Key takeaway
INEMA projects and courses about this