In modern web architectures, SSRF vulnerabilities have become increasingly difficult to exploit due to sophisticated defense mechanisms. This presentation introduces SSRF² - a novel technique that challenges fundamental assumptions about trust boundaries by using the same SSRF primitive twice across different security contexts. Through real-world discoveries, we demonstrate how a seemingly limited SSRF primitive, when used twice, can bypass an entire security stack designed to prevent internal access. What makes this technique particularly powerful is its ability to transform restricted blind SSRF vulnerabilities into critical security breaches without complex chains or extensive reconnaissance.