I have the same issue with PI 1.8.8-3 x64 MacOSX
My Fortigate router/gateway is configured to do a deep inspection of SSL Certificates. In this mode PI repository fails, if I relax from deep inspection to just inspection (where it basically just inspects the header) PI repository works fine. About 2 - 3 weeks ago I went to SSL deep inspection and had problems with ThinkorSwim platform as well. Not sure why this causes an issue, but SSL deep inspection intercepts the certificate, picks it apart to analyze it and re-assembles. Perhaps your issue is something similar.