Engagement PlanningAll engagements must start with Engagement Planning, the first step in a Red Team engagement. It is not possible to conduct a professional and successful execution without fully understanding the goals and scope of the engagement, understanding the
resources required to execute, and creating a solid plan.
Cost and FundingAs with any security effort, cost and funding are significant
influencers in planning, scheduling, and executing a Red Team engagement. Several factors contribute to the overall cost and scope of an engagement. Each element should be carefully reviewed and documented explicitly in a contractor agreement. Regardless of team status (internal or external service provider, each factor applies.
ScopeScope plays the most significant role in the overall cost of an engagement. Consider scoping a vulnerability assessment. There is often a considerable benefit and
need to conduct a full-scope, in- depth review of every node in an environment. The equipment and software employed are usually part of the priceless additional licensing requirements, setup and configuration are already being conducted, and the addition of target space to the contract is generally cost-effective. This scoping effort is arguably straightforward and typically broken into the asset type being assessed. Scoping could
be split into workstations, servers, network components, or any logical asset category.
Now consider scoping a Red Team engagement. There are significant differences between an in-depth assessment of 1,000 nodes vs. one of 14,000 nodes. Accurate assumptions about the environment can be made based upon the data obtained from a few similar nodes however, this data does not necessarily enable the Red Team to meet the objectives of the engagement.
In general, as a target environment grows, so does the complexity of its security controls (and ideally its effectiveness).
Sometimes, that complexity benefits the environment. Other times,
it introduces weaknesses a RedTeam may use advantageously to gain access or achieve threat-based goals. In either case, the Red
Team has to manage the complexity of tactics to test and validate the overall threat strategy accurately.
Red Teams are known for leveraging multiple systems or data points and "bending" configurations to meet the engagement's needs. Common security tools and applications don't regularly discover many of these flaws or paths. This understanding drives scope development toward a scenario rather than testing every node in a target environment using standard security testing tools. The scope should always directly and effectively support the operational objectives being measured.