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As per https://github.com/git-for-windows/git/issues/4350#issuecomment-1485041503, the major block for upgrading Git for Windows' OpenSSL from v1.1 to v3 is the tricky part where such an upgrade would break `git fetch`/`git clone` and `git push` because the libcurl depends on the OpenSSL DLL, and the major version bump will _change_ the file name of said DLL. To overcome that, the plan is to build libcurl flavors for each supported SSL/TLS backend, aligning with the way MSYS2 builds libcurl, then switch Git for Windows' SDK to the Secure Channel-flavored libcurl, and teach Git to look for the specific flavor of libcurl corresponding to the `http.sslBackend` setting (if that was configured). Here is the PR to teach Git that trick.