I have recently upgrade my computer to Mavericks and at the same time upgraded the Postgres.app to 9.3. In doing so, I broke something; after the upgrade I was getting a nasty error message using virtualenvs I created pre-upgrade. And of course the warning was not helpful! So I had to figure out what happened myself.

What to do? I took some time to research what was needed to be done, if anyone else was getting similar issues, and had a hard time locking anything down. Luckily, I came across this Stack Overflow Page. In reading the answers, I started to understand what might have happened. Below is what I did to fix the problem, and hopefully it will help someone else.

First, copy the updated libssl.dylib file from the Postgres.app location:

$ sudo cp /Applications/Postgres.app/Contents/MacOS/lib/libssl.1.0.0.dylib /usr/lib

Then I created a new symbolic link from the copied libssl.1.0.0.dylib file to the standard libssl.dylib file located in /usr/lib.

$ sudo ln -fs /usr/lib/libssl.1.0.0.dylib /usr/lib/libssl.dylib

The -f flag will remove the existing link before creating the new one.

After I completed this, it seemed like the old virtualenvs worked without a hitch. I am not sure why this happened; whether it was due to the upgrade to Mavericks, the upgrade to Postgres.app 9.3 or a combination of both, but it was quite frustrating. Hope this explanation helps someone…

Let me know on Twitter if anyone has a better way of doing this or something above is wrong. Thanks!