Two "different" openssl.exe files on Windows x64 Install

[FastEddieAustin]

I noticed that I have two openssl.exe files which indicate they are both 3.5.4, but if I generate an SHA256 hash they are different and a directory listing shows they are different sizes which you would expect. Curious why we have two copies of the file and what is the difference between the two beyond the implication that the one in the mingw64 folder might come from https://sourceforge.net/projects/mingw-w64/?

C:>"c:\Program Files\Git\mingw64\bin\openssl.exe" version
OpenSSL 3.5.4 30 Sep 2025 (Library: OpenSSL 3.5.4 30 Sep 2025)

C:>"c:\Program Files\Git\usr\bin\openssl.exe" version
OpenSSL 3.5.4 30 Sep 2025 (Library: OpenSSL 3.5.4 30 Sep 2025)

C:>certutil -hashfile "c:\Program Files\Git\mingw64\bin\openssl.exe" SHA256
SHA256 hash of c:\Program Files\Git\mingw64\bin\openssl.exe:
060b787efc1e058068bfe4ff1c162fc40173df33fff8ceac6543d1ebaf340424
CertUtil: -hashfile command completed successfully.

C:>certutil -hashfile "c:\Program Files\Git\usr\bin\openssl.exe" SHA256
SHA256 hash of c:\Program Files\Git\usr\bin\openssl.exe:
2c6f2c64612cf45349f15850e4647b2fe594c2759de63a695ec4cbe13b2404da
CertUtil: -hashfile command completed successfully.

Directory of c:\Program Files\Git\mingw64\bin

11/17/2025 06:24 PM 1,044,636 openssl.exe
1 File(s) 1,044,636 bytes

Directory of c:\Program Files\Git\usr\bin

11/17/2025 06:24 PM 1,003,388 openssl.exe
1 File(s) 1,003,388 bytes

[dscho]

Yes, those two openssl.exe files are different. One is a pure Win32 variant ("MINGW"), the other relies on the POSIX emulation layer provided by the MSYS2 runtime ("MSYS"). For a detailed explanation, see https://gitforwindows.org/the-difference-between-mingw-and-msys2