Generative AI: Exposing Risky Parsing Gaps in WAFs

Executive summary
Attackers have moved beyond simple signature evasion. Many successful attacks now exploit the way different parts of a web stack disagree about the meaning of the same request. Increasingly, generative AI tools allow attackers to automate and accelerate this process - rapidly generating and testing thousands of small request variants to probe for parsing differences that a WAF might miss.
A WAF may accept a request that the application subsequently interprets very differently, which lets malicious content slip through without raising an alert. RedShield’s application security service includes in-flight security patches which address this by operating in the traffic path to normalize ambiguous inputs and apply targeted fixes to known weaknesses - without touching the application's code. This means transforming incoming HTTP requests so that any unusual, inconsistent, or non-standard formatting is cleaned up and made consistent before the request reaches the application. The result is
Why WAF‑only defenses struggle today
A modern web request passes through a CDN or proxy, a WAF, and finally the application framework. Each layer parses and interprets that request. If those interpretations differ, an attacker can craft inputs that look harmless to the WAF but resolve into something dangerous at the application. Generative AI makes it easier for adversaries to do this inexpensively and at scale. Typical examples include mixed or malformed content types, repeated parameters in a form, or conflicting headers that cause one system to read a body while another ignores it. None of this requires exotic techniques - only careful manipulation of edge cases that arise in the gaps between components. The problem is not a lack of rules; it is that rules attached to an approximate understanding of a request do not control the behavior that matters. You end up with tuning cycles, exceptions for legitimate traffic, and lingering audit findings while engineering teams schedule code changes.