Hi EJR,
Thanks for reaching out to Microsoft Q&A.
Yes, Microsoft performs regular penetration testing on their systems. They consider security to be a critical aspect of their services and infrastructure. Microsoft has dedicated security teams that conduct penetration testing to identify and fix vulnerabilities within their software and hardware env's. This is part of their commitment to maintaining strong security practices and compliance with various regulatory standards, including GDPR, HIPAA, and ISO/IEC 27001.
Moreover, Microsoft encourages and supports external security researchers through their Microsoft Security Response Center (MSRC) and offers bug bounty programs, where security researchers are incentivized to report vulnerabilities in exchange for rewards. This external testing complements their internal efforts to secure their systems and services.
Microsoft typically doesn't detail all specifics of their internal security procedures publicly, as revealing too much could weaken their security posture, but they do provide assurance that these tests are a regular part of their security lifecycle.
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