On October 14, Microsoft will cease support for Windows 10, impacting healthcare organizations that rely on legacy applications. Migrating to Windows 11 typically takes six to nine months and involves creating a new system image, testing applications, re-imaging devices, training staff, and rolling out the new OS. Microsoft will offer an Extended Security Updates (ESU) program for up to three years post-Windows 10 end-of-service, but many organizations struggle with maintaining a Microsoft Enterprise Agreement due to financial issues. Healthcare organizations often use 150 to 300 applications, making them vulnerable to cybercriminals, especially as the end of Windows 10 support approaches, with potential HIPAA violations looming. Cyber insurance implications arise, as claims may be denied if breaches occur due to unsupported systems, leading to increased premiums. Windows 11 includes enhanced security features like TPM 2.0 and a Diagnostic Data Viewer. Cybercriminals are expected to target Windows 10 users after support ends, emphasizing the need for organizations to plan their transition to mitigate risks.