Updating OpenSSL in OSX I am using 10.9 with Server app 3, and right now i am using an obsolete connection with TLS 1.0, RSA and AES_128CBC with HMAC-SHA1 (that cames by default).

While i was trying to upgrade openssl, i notice that when i tried to upgrade it says that openssl is not installed but it is.

remote:~ root# port upgrade openssl
Error: openssl is not installed
remote:~ root# openssl version
OpenSSL 0.9.8zg 14 July 2015


So i would like to know how can i upgrade it, and why is not being detected as installed?
OpenSSL 0.9.8zg 14 July 2015 is the version installed by OS X 10.9(.5) (Mavericks) and resides in /usr/bin/.

MacPorts neither installs nor updates/upgrades genuine Apple (OK, OpenSSL is not Apple but it's part of their basic BSD package) system software. MacPorts' standard realm is /opt/...

You would have to install a newer OpenSSL version with MacPorts - if available.