Tabletop: “you have 400 servers; 800 users and your…

CISO Tabletop Scenario Intro

I thought it would be fun to explore what people do with regards to Cyber Securityleadeship, budgets, contraints and realities of business change. So here’s a blog post to supliment my thread on twitter:

MrR3b00t | #StandWithUkraine #DefendAsOne on Twitter: “Tabletop: you have 400 servers, 800 users and your cyber security budget is 100K…. what do you do? https://t.co/Nw0Pd7rH8L” / Twitter

please note: the list below is based on experiance, it’s also a list I made whilst drinking about half a cup of tea so it’s not complete or “the answer” it’s just some observations about an approach I advocate.

Leadership

Why do “we” suck so badly at digital security…

Everything is fine until it’s not

I’ve been travelling to different organisations and visiting different networks for a while and whilst each organisation is unique (they really are) their operating models, technology challenges and weak security postures generally aren’t as unique as the organisational itself.

One thing that does spring to mind however is that there is a massively common pattern we find with organisations.

Those that invest well have better postures, better technology experiences and an improved security posture.
Those that don’t historically invest well, well they have quite the opposite:
- They don’t train staff
- They have very weak postures
- They carry an extraordinary volume of business risk

One thing that is common though, is that all of this tends to link to financial investments, so executives and boards usually have some idea if they are spending or not in this space, what they commonly don’t have a good view on is they getting what they “thought they were buying”. Sadly, too often what they assumed was “in the box” with the “IT provision” with regards to quality and cyber security just simply isn’t the case. Everything is fine, until you look… then it’s less than fine! So, what can we do about it?

Architecture

The difference between what can be vs what often…

I’ve travelled all over the internet, I’ve worked with logs of organisations from banks through to small ISVs and one thing I would say is fairly universally true. What can be isn’t what is.

There’s a lot of different operating models and technologies in the world. There’s logs of differen’t specifics. This diagram here is not mean’t as a refrence architecture but more as an indicator.

There is also a massive reality people must understand, cyber good most definatley costs more at the point of deployment than cyber bad. Cyber bad’s ROI is truly variable and in mind mind is too hard to measure. For one org with cyber bad can experiance a significant breach (and cost) and another may have lady luck on their side.

Defense

Infection Monkey Overview

Have you ever wanted to see what would occur in an environment if a worm was a make its way in? I often work with customers to show them about lateral movement from a human operated perspective however sometimes it’s useful for people to visualise this better and to demonstrate what could occur if a worm was set loose. A great tool to help with this is Infection Monkey from Guardicore (https://www.guardicore.com/

High Level View

The process steps are as follows:

Scope Exercise
Prepare Environment
Deploy Infection Monkey Server (Monkey Island)
- Configure Server Credentials
Monkey Configuration
Release Monkey/s
Review
Report

Read more “Infection Monkey Overview” →

Guides

What do you need to be Cyber Leader?

Introduction

What does it take to be a cyber leader? How do we address a broad challenge we have in today’s business world?

There are a huge number of organisations whereby the leadership do not have domain expertise in cyber and related disciplines. There are decision makers who are having to best guess. On the other end of the spectrum, we have thousands and thousands of people trying to “break into cyber” yet they face largely insane entry requirements with the forementioned adding things to junior and entry level role which include:

Must have a CISSP (CISSP requires 5 years’ experience and is an Information Security certificate that is very broad and not very deep, it also covers a range of areas that in my opinion aren’t even required for many cyber security capabilities inside organisations)
Must have a Certified Ethical Hacker (this exam includes remember historic malware dates, is that really what we need from our leaders?)
Must have a very large level of experience of be from an existing cyber role

Defense

Changing a security posture requires changing your own behaviours

I’m sure you will have had a marketing firm or some random sales person on Linkedin tell you that security should be simple and that their product will save you from all the ATPs and nation state hax0rs under the sun. However let’s get real, thats almost certainly not true and also security isnt simple or we’d all be out of jobs and everyon woulndn’t be getting owned all the time.

Getting real

Defense

Ransomware Defence Checklist – Part 1 : Initial Access

Defending the Realm

We keep seeing organization get hit, in some kind of a sick way I think me and some of my friends in the industry are bored with the over dramatic responses of “sophisticated” “advanced” and “unpreventable” because most times the kill chains simply are not like this. But still the onslaught keeps coming. Well I know this much, whilst I would love to deploy with the team and harden everyone’s networks that simply isn’t possible. So what we thought we would do is write something to try and spread the knowledge a bit further and hopefully have some positive impact.

Ransomware 101

It’s not just that your data will be encrypted, it will likely be exfiltrated and sold. You will likely have access sold, data sold and be extorted. The Ransomware business model is adapting to defender responses. Even if you can restore from backup they will likely try and attempt to extort. This brings a key point in this equation, the best position is to NOT get pwn3d to start with. Ok that might sound silly to say but when we look at these kill chains you might start to see the world from my perspective a little. Read more “Ransomware Defence Checklist – Part 1 : Initial Access” →

Defense

Cyber Defence is Hard

Introduction

If you read a book about management theory or specifically cyber security management you will find lots of frameworks, methods, formulas, models etc. None of them really let you know how insanely hard it can be to defend a moving target where regardless of how many controls you have, all it takes it someone doing something which may seem bonkers to you but perfectly reasonable for them. Their objective is to do business in an efficient manner, your objective is to protect the business in an efficient manner. Fundamentally these two things are not at odds, but there are a lot of human factors that come into play on top of some serious technical challenges. Read more “Cyber Defence is Hard” →

Defense

The grass is always greener, until it is not

A PwnDefend Story – Day 7

It is a blur so far, I figured after the last place the grass would be greener, surely no one else has that many security challenges. I did some due diligence during the interview process, they seemed very confident about having certifications and that they took security seriously. hell, that should have set some red flags off but even the cynical sometimes hope that it is as someone says.

I have started to work myself around the board and I am making friends with people, my diary is filled with zoom calls and my notebook is already many pages deep.

You cannot make this stuff up though, day two and I’ve dealing with a business email compromise incident, the phishing page was not even in good English but then it only takes a second or so whilst in a meeting to not quite realise your running on autopilot so you cannot blame people. Hell, the branding was copied so we know it was a targeted phish. It would have been nice to at least had centralised logs for the team to analyse though. Read more “The grass is always greener, until it is not” →

Defense

5 Major Challenges with Business Digital Security

This is not meant to be an essay, but simply a rapid-fire view of things that I see that are major challenges with digital security in today’s age. So, without any further delay let us hit it: