We should always base decisions on a risk analysis, even when we consider deviating from our security standards. After we do the risk analysis and the risk is calculated, we may choose to enforce the security standard, make changes to the proposed system change, or add mitigating controls, but we would need the risk analysis to determine if any of those are suitable. We would never just do any of them without the proper analysis.

We would want a very strong key storage, if the attackers can get to our encryption keys, most of the other security measures are irrelevant. Most encryption today is strong enough to not be breakable with current technologies, making it stronger does often not make it significantly more secure. Complex firewall rules do not mean more secure, and in this example is a distractor. We would want user authentication in all applications, but not relevant for this question.

VPNs allow our staff to connect securely, because the traffic is encrypted in the VPN tunnel. We would want 2FA with the VPN, and we definitely do not want to remove it. We would not want to have less complex passwords, and VPN's may or may not reduce administrative overhead, for this question it is irrelevant.

Reconnaissance is one of the phases of an attack or penetration testing, it is not a form of social engineering. Vishing (voice phishing), authority, and scarcity are all types of social engineering.

The owner of the data is always responsible for classifying the data, they know the best how sensitive (or not) their data is. The data custodian would do the practical things (patches, security, updates), but never classify anything. The CISO or the DBA are not appropriate for assigning sensitivity, they may have no clue what the data is or how sensitive the data is.

We need to start looking at encryption key management in the initiation or planning phase of the project, when we develop our project requirements. If we do not do it until programming, deployment or debugging, we are doing it after the fact, and it will be bolt-on security. It will never be as secure as security designed in as a functional requirement.

We always implement countermeasures that are appropriate for the risk, that is why we clearly classify and determine the sensitivity of our assets. Protection cost being appropriate for sensitivity makes no sense, we base the appropriate cost on the risk. Naturally we want risks to be minimized and sensitive assets are protected, but that is not why we do the classification.

Governance is directly tied back to the organization's strategy, vision and mission. Our technological constraints, the legal requirements, and the potential for lawsuits is important, but the primary driver is our strategy.

The first thing we should assess is if our current controls are sufficient. If they are there is no need to meet with the financial or legal teams, nor update any policies or procedures. Risk analysis of the compliance would come much later, if we decide our current countermeasures are not sufficient.

It is MOST important to have very clearly defined goals and objectives for the penetration test. We would also possibly have certain timeframes the attackers are allowed to use, certain IP ranges, and also clear guidance on what they are not allowed to do. We may have them try to access a test system, but that is after the clear goals and objectives. On top of that test systems often do not have the same posture as production systems, being able to get access to a test system may not mean they can access our production systems. We may inform the IT staff, but not always. Senior management HAS to know about the penetration test, they sign off on it, and they are ultimately liable.