This presentation was made at BSides MCR 2014. It tackles the subject of SSL/TLS testing from the viewpoint of a penetration tester. It is a practical guide, broad in scope, focusing on pitfalls and how to check issues manually (as much as possible).
I already have updated material (including SNI and OCSP Stapling) for the next version. Look out for future content @exploresecurity and @NCCGroupInfosec.