5 Red Team Exercises That Expose Your Real Security Gaps in 2025

I’ve seen it time and again throughout my career: companies spend millions on security tools but still fall victim to basic attacks. As someone who’s spent over a decade in the security trenches, I can tell you that fancy dashboards don’t matter if your basics aren’t solid.

The truth? If you want to know your real security position, you need red team exercises that show what actually matters. I’m not talking about basic tests that scan for known bugs – I’m talking about exercises that mirror how real attackers work in 2025.

Here are five red team exercises that will show your true security gaps – the ones that lead to breaches. For each, I’ll add template links later to help you plan these tests.

1. Social Engineering Campaigns: People Are Still Your Biggest Vulnerability