Microsoft Security: A World First

September 30, 2024

green-dino_thumb_thumb_thumb_thumb_t[2]This essay is the work of a dumb dinobaby. No smart software required.

After the somewhat critical comments of the chief information security officer for the US, Microsoft said it would do better security. “Secure Future Initiative” is a 25 page document which contains some interesting comments. Let’s look at a handful.

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Some bad actors just go where the pickings are the easiest. Thanks, MSFT Copilot. Good enough.

On page 2 I noted the record beating Microsoft has completed:

Our engineering teams quickly dedicated the equivalent of 34,000 full-time engineers to address the highest priority security tasks—the largest cybersecurity engineering project in history.

Microsoft is a large software company. It has large security issues. Therefore, the company undertaken the “largest cyber security engineering project in history.” That’s great for the Guinness Book of World Records. The question is, “Why?” The answer, it seems to me, is, “Microsoft did “good enough” security. As the US government’s report stated, “Nope. Not good enough.” Hence, a big and expensive series of changes. Have the changes been tested or have unexpected security issues been introduced to the sprawl of Microsoft software? Another question from this dinobaby: “Can a big company doing good enough security implement fixes to remediate “the highest priority security tasks”? Companies have difficulty changing certain work practices. Can “good enough” methods do the job?

On page 3:

Security added as a core priority for all employees, measured against all performance reviews. Microsoft’s senior leadership team’s compensation is now tied to security performance

Compensation is lined to security as a “core priority.” I am not sure what making something a “core priority” means, particularly when the organization has implement security systems and methods which have been found wanting. When the US government gives a bad report card, one forms an impression of a fairly deep hole which needs to be filled with functional, reliable bits. Adding a “core priority” does not correlate with security software from cloud to desktop.

On page 5:

To enhance governance, we have established a new Cybersecurity Governance Council…

The creation of a council and adding security responsibilities to some executives and hiring a few other means to me:

  1. Meetings and delays
  2. Adding duties may translate to other issues
  3. How much will these remediating processes cost?

Microsoft may be too big to change its culture in a timely manner. The time required for a council to enhance governance means fixing security problems may take time. Even with additional time and “the equivalent of 34,000 full time engineers” may be a project management task of more than modest proportions.

On page 7:

Secure by design

Quite a subhead. How can Microsoft’s sweep of legacy and now products be made secure by design when these products have been shown to be insecure.

On page 10:

Our strategy for delivering enduring compliance with the standard is to identify how we will Start Right, Stay Right, and Get Right for each standard, which are then driven programmatically through dashboard driven reviews.

The alliteration is notable. However, what is “right”? What happens when fixing up existing issues and adhering to a “standard” find that a “standard” has changed. The complexity of management and the process of getting something “right” is like an example from a book from a Santa Fe Institute complexity book. The reality of addressing known security issues and conforming to standards which may change is interesting to contemplate. Words are great but remediating what’s wrong in a dynamic and very complicated series of dependent services is likely to be a challenge. Bad actors will quickly probe for new issues. Generally speaking, bad actors find faults and exploit them. Thus, Microsoft will find itself in a troublesome mode: Permanent reactions to previously unknown and new security issues.

On page 11, the security manifesto launches into “pillars.” I think the idea is that good security is built upon strong foundations. But when remediating “as is” code as well as legacy code, how long will the design, engineering, and construction of the pillars take? Months, years, decades, or multiple decades. The US CISO report card may not apply to certain time scales; for instance, big government contracts. Pillars are ideas.

Let’s look at one:

The monitor and detect threats pillar focuses on ensuring that all assets within Microsoft production infrastructure and services are emitting security logs in a standardized format that are accessible from a centralized data system for both effective threat hunting/investigation and monitoring purposes. This pillar also emphasizes the development of robust detection capabilities and processes to rapidly identify and respond to any anomalous access, behavior, and configuration.

The reality of today’s world is that security issues can arise from insiders. Outside threats seem to be identified each week. However, different cyber security firms identify and analyze different security issues. No one cyber security company is delivering 100 percent foolproof threat identification. “Logs” are great; however, Microsoft used to charge for making a logging function available to a customer. Now more logs. The problem is that logs help identify a breach; that is, a previously unknown vulnerability is exploited or an old vulnerability makes its way into a Microsoft system by a user action. How can a company which has a poor report card issued by the US government become the firm with a threat detection system which is the equivalent of products now available from established vendors. The recent CrowdStrike misstep illustrates that the Microsoft culture created the opportunity for the procedural mistake someone made at Crowdstrike. The words are nice, but I am not that confident in Microsoft’s ability to build this pillar. Microsoft may have to punt and buy several competitive systems and deploy them like mercenaries to protect the unmotivated Roman citizens in a century.

I think reading the “Secure Future Initiative” is a useful exercise. Manifestos can add juice to a mission. However, can the troops deliver a victory over the bad actors who swarm to Microsoft systems and services because good enough is like a fried chicken leg to a colony of ants.

Stephen E Arnold, September 30, 2024

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