In this edition of the Soap Box podcast we’ll be hearing from Ryan Kalember, the EVP of cybersecurity strategy at Proofpoint, a company best known for being an email filtering giant.

Proofpoint’s biggest challenger in that space is Microsoft, and if you’ve been paying attention you’d know that Microsoft is doing an absolutely massive push into the security space. It claims security is a $10bn revenue centre for the company, which is a bit of a screwy situation given a lot of the insecurity its security products mitigate is introduced through deficiencies in its core products.

And, largely, that’s what this interview is about – the screwy incentives that are driving Microsoft’s decisionmaking. More emphasis on security product development, and less effort on securing its core products.

Of course it’s self-serving for Ryan and Proofpoint to give Microsoft a kicking, given Redmond is its primary competitor. But the thing is, Ryan makes some very good points.

We talk about the incentives thing, and then we talk about why active directory is a trashfire and why the replication of the domain trust model in AzureAD is going to eventually bite us all in the ass. The circle of life, enterprise computing fail edition. Enjoy.