I have created a little script that automates downloading, compiling and testing multiple versions of OpenSSL. It's a bit of a hack but it suits its purpose. Maybe somebody likes to take it from here and turn it into a proper tool for Python's Tools/ directory.

From the doc string of the script:

The script

  (1) downloads OpenSSL tar bundle
  (2) extracts it to ../openssl/src/openssl-VERSION/
  (3) compiles OpenSSL
  (4) installs OpenSSL into ../openssl/VERSION/
  (5) forces a recompilation of Python modules using the
      header and library files from ../openssl/VERSION/
  (6) runs Python's test suite

The script must be run with Python's build directory as current working directory.

The script uses LD_RUN_PATH, LD_LIBRARY_PATH, CPPFLAGS and LDFLAGS to bend search paths for header files and shared libraries. It's known to work on Linux with GCC 4.x.

Tested with OpenSSL 0.9.7m, 0.9.8y, 1.0.0k and 1.0.1e.