With openssl, any update requires that all packages that are built against it be recompiled. There are over 50 extensions last time I counted that use openssl. I have no intention of forcing an openssl update and a recompile of it's dependent extensions, even as part of a major TC version upgrade when that time comes.
What I am planning is to make an openssl extension that is self contained under /usr/local/openssl-1.0.0(/bin,/lib,/etc) when version 1.0.0 is stable. Then anyone who wants to use the newer openssl can compile against it and use a wrapper script so the apps can find the ssl libraries. And those newer libs won't be found by ldconfig so they won't interfere with the current openssl libraries in the system. Wrappers were used a lot with the .uci extension type that was installed into /opt and had supporting libs packed in with the extension.
There are several approaches that can be considered when building apps with ssl support.
1. Use the existing extension installed into /usr/local that is recognized by ldconfig. This version I think should remain at 0.9.8h from now on to support the many existing ssl enabled extensions.
2. Make use of the shared libraries of an updated extension installed self contained into /usr/local/openssl-$version and use wrapper scripts to make use of those libs. That is, when it becomes available. This is what I plan to do eventually with my own ssl apps.
3. Compile ssl support statically into an app. Though this makes the extension larger, it makes it independent of needing openssl libraries installed in the system. And the latest available version of openssl can be used to do this regardless of openssl extensions available.
4. Include your own build of openssl libraries with your extension, self contained in a directory that is not found by ldconfig so as to not interfere with the current ssl extension and use a wrapper to find the libraries. Though not space saving as the ssl libs would be included with each extension, this also lets you use the latest and greatest ssl.
Though we now use a modular, shared library approach to extensions and normally use standard install paths, I think openssl is one where we may be better in the long run to consider an approach that will not require a rebuild of apps and allow a smooth transition to a newer openssl version.