Ashley Madison was a deeply risky proposition for its client, yet the clients took a risk and trusted the site with their most important asses, their dignity. Unfortunately, it was found that Ashley Madison was on operating on risky grounds, since it overlooked various aspects of their network and system security infrastructure. Ultimately these loose business practices led to a disaster, ironically Ashley Madison betrayed its own loyal clients. In the media, Ashley Madison hack has published a lot, but no full account of technically how the system was exploited and timeline has been presented at this time. This is a shame since a lot can be learnt from Ashley Madison compromise. My talk will provide the technical story behind the exploit, compromise timeline and present the lessons learnt.