As of version 13.0, CrossOver no longer uses this library. This article left in place for reference only.
The libcrypto and libssl libraries normally come as a pair. Using a mismatched pair is likely to result in crashes and other misbehavior.
CrossOver no longer uses libcrypto and libssl as of 13.0 (but cxdiag incorrectly continued to check for it until CrossOver 15).
This issue should not happen on a normal system. As such, when it does happen it is likely to be caused by a unique set of circumstances which makes it hard to provide general steps for its resolution.
That said you may first check whether either library is an old version left over after an upgrade. For instance a libcrypto.so.0.9.7 file with no matching libssl file but current 0.9.8 files for libcrypto and libssl. If that's the case you may delete the lone file after double checking with your package manager that it is not mean to be there (use dpkg -S or rpm -qf there).
We're rebels. We're misfits. But mostly, we're software liberators. And we're very, very good at what we do. We have to be. Lots of developers work with open source, but only a tiny fraction of those are good enough to get software that was designed for one platform to work on another one. We invented CrossOver software - a unique approach to cross-platform compatibility that does not require dual-boot or another OS license. We launched PortJump to help app and game developers broaden their market beyond Windows® users. And we launched ExecMode to help organizations solve really ugly technical challenges.