We are running an old version of OpenSSL 0.9.7e and would like to upgrade to the most current. Our server is running Debian, and I am wondering if there would be any issues with just upgrading it using apt-get?
Would we have to worry about anything breaking, or updating any configurations?
That version of OpenSSL was released in 2004. Therefore, it sounds like you should be upgrading more than just OpenSSL, as Debian is no longer releasing security updates for any version of Debian older than then current 'lenny' release.
There have been many changes to OpenSSL since 0.9.7e, and upgrading it may break programs that are linked against it. As has already been mentioned, it's best to upgrade the system as a whole, which should hopefully capture all the dependencies. If that's not an option, then you'll have to go through and determine from the package tools what packages depend on OpenSSL, and cherry pick what to upgrade.
