Because OpenSSL's version numbers are not compatible with the CocoaPods version numbering, we will agree on the following.
OpenSSL version: A.B.CD will become A.B.C*100 + place of D in the alphabeth.
Example: OpenSSL 1.0.1h => OpenSSL 1.0.108
With the new Cocoapods "trunk" system, a Pod has a maintainer. Being the maintainer of the OpenSSL pod, I will try my best to keep it updated. If however, you see that the Pod is way behind, please submit a pull request with the changes and I'll submit it to Trunk after review.