This article explains how to simulate an SSL session from the P8.

Note: This option does not simulate the connection through the proxy, it is used to test SSL connection to a website from P8 itself and is useful in determining any issues that may exist with SSL connectivity to the website.

1. SSH to the P8
2. At the cmd line type "openssl s_client -connect <websiteaddress>:443". E.g openssl s_client -connect outlook.office365.com:443
3. Once connected type "get https://<url> HTTP/1.0" then hit "enter" and "enter" again. E.g "get https://outlook.office365.com/owa/ HTTP/1.0" should show something similar to the below: