During the upgrade to Vault Professional 2026, the pre-check tool fails when IIS is configured with valid HTTPS bindings and an SSL certificate — even when everything is functioning correctly and accessible over HTTPS. Problem Observed: The installer attempts to access the file: http://localhost:443/TestASP/TestASPNetStatic.txt This is an invalid use of port 443, which is reserved for HTTPS. This causes a false failure in the pre-check step "Checking ASP Status", even though: IIS bindings are correctly set to "All Unassigned" HTTPS is enabled and working The certificate is valid and trusted under its assigned domain Root Cause: The pre-check tool is hardcoded to test localhost over HTTP, even when SSL is enabled. It does not validate or accept HTTPS responses, nor does it adapt to hostname + certificate logic. Users must resort to a workaround: temporarily removing HTTPS bindings from IIS to pass the installer check, which introduces risk and adds unnecessary steps. Recommendation: Update the Vault installer logic to support and properly verify HTTPS bindings. Adjust the ASP test to use the correct URL scheme: https://<server-FQDN>/TestASP/TestASPNetStatic.txt Ensure the pre-check respects: IIS bindings using "All Unassigned" SSL certificates matching the FQDN or SAN Functional HTTPS responses (including from internal or self-signed certificates) Benefit: This improvement would streamline enterprise deployments, eliminate unnecessary workarounds, and align Vault installation workflows with modern IT and security standards.
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