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My Microsoft wish list for 2019

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From a business perspective, Microsoft had a pretty good 2018. That’s especially true when you examine the company’s revenue, profits, stock price, and momentum against other giant tech companies, especially Apple, Google, and especially Facebook. Those three stalwarts of the once-mighty FAANG displayed rare weakness in 2018, while Microsoft looks poised to end the year with the largest market cap of any publicly traded company in the world.

That’s pretty good for a company that has been written off as a dinosaur multiple times since the turn of the 21st Century.

But 2019 is a new year, with new challenges and opportunities. In that spirit, I offer congratulations to CEO Satya Nadella on an excellent year, along with some suggestions for how to keep that momentum going.

My wish list might not pass muster with Redmond’s legions of MBAs intent on squeezing every last dime from the pockets of Microsoft customers. Instead, my suggestions are designed to earn the enduring loyalty of those customers. As Facebook proved this year, you can’t take that loyalty for granted.

On privacy, move to the high ground and stay there.

Privacy is the defining issue in technology today. Just ask Facebook, whose reputation is in tatters after a year of devastating revelations about its alternately incompetent and malevolent (and occasionally both) treatment of its customers’ data. Google has so far avoided the public tarring-and-feathering that Zuckerberg and Co. have earned, but their business model, tied to zealous collection of personal information, makes them a constant target.

That creates a rare opportunity to do the right thing, morally and legally, and reap long-term economic benefit from it.

Apple discovered this year that privacy is a winning argument, with CEO Tim Cook arguing that “[o]ur own information, from the everyday to the deeply personal, is being weaponized against us with military efficiency.” It’s an argument that Apple has been making for years, but in 2018 it finally hit home, especially after Facebook’s “dire” privacy blunders.

Microsoft’s history on privacy issues is checkered, to say the least. A decade ago, Microsoft’s developers were ready to implement an anti-tracking feature in Internet Explorer. Unfortunately, that feature never shipped; instead, it was killed by a competing faction that was convinced it could make billions from online advertising: Bad Microsoft defeated Good Microsoft.

And don’t get me started on the painful, self-destructive “Scroogled” campaign.

But this is a new era and a new Microsoft, and a genuine commitment to protecting the personal and business data of its customers across the board would be welcome. The company’s decision to extend the rights available under the European Union’s General Data Protection Regulation to customers worldwide is an excellent start. Please keep it up.

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Make Windows 10 updates less painful.

After more than four years of development, Microsoft has settled into a rhythm with its Windows 10 development process. Alas, it’s not a “smooth jazz” rhythm but instead has all the aesthetic appeal of a jackhammer ripping up concrete outside your office window.

This year’s October 2018 Update was the definite low point, forcing Microsoft to take the unprecedented step of pulling the feature update from its servers and finally re-releasing the October update more than a month later.

There’s no question that the entire episode was an embarrassment, and Microsoft will no doubt learn some serious lessons from the entire affair. But as far as I am concerned the first and most important step is to eliminate mandatory twice-a-year feature updates.

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Stop with the shovelware already.

Beginning with the release of Windows 10 in July 2015, every SEC-mandated 10-Q and 10-K report filed by Microsoft Corporation included this boilerplate statement: “[W]e anticipate that Windows 10 will enable new post-license monetization opportunities beyond initial license revenues.”

The first salvo included piles of crappy apps splattered onto your Start menu whether you want them or not, including Candy Crush Soda Saga, Bubble Witch 3 Saga, and March of Empires. That infestation even includes PCs sold with Windows 10 Pro, which seems to be a lousy way to treat your best customers.

When I wrote about Microsoft’s plans to milk more profits out of its Windows 10 cash cow early in 2018, I predicted that more details about those “monetization opportunities” would arrive soon. Sure enough, with its July 2018 annual report, that vague text became significantly more concrete:

Our ambition for Windows 10 is to broaden our economic opportunity through three key levers: an original equipment manufacturer (“OEM”) ecosystem that creates exciting new hardware designs for Windows 10; our commitment to our first-party premium device portfolio; and monetization opportunities such as gaming, services, subscriptions, and search advertising.

You know what’s not in that list? Stupid games like Candy Crush. Also not on the list are any kind of ads in Windows itself, outside of search-based functions.

That’s a good call. The appeal of advertising inevitably leads to temptations to weaken privacy settings, so reducing projections of ad revenue is a very good thing. And even in those places where ads are expected, there should be an easy ad-free option available.

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Don’t repeat the XP mess with Windows 7.

The year 2019 will officially end on New Year’s Day, 2020. But Microsoft’s product planners are no doubt looking two weeks further into the future, to January 14, 2020. That’s when Windows 7 officially reaches its end-of-support date.

If you’re the glass-half-full type, that’s a good problem to have. After all, it means your customers are so loyal that they’ll stick with your products for a decade or more.

Unfortunately, out in the real world, the glass is at least half empty. The last time this happened was when Windows XP reached its end-of-life date in 2014. The number of laggards was painfully large, especially in the public sector, and they remained in the refusenik camp for years. The result, as every security professional remembers, was a massive worldwide ransomware outbreak that forced Microsoft to release an XP patch in May 2017.

In interviews, Microsoft’s executives have assured me that the migration from Windows 7 to Windows 10 is going swimmingly. But those assurances belie the inconvenient reality that when that end-of-support date rolls around a little more than a year from now, the percentage of PCs running Windows 7 will continue to be significantly higher than a few percent.

The good news for enterprise customers is that Microsoft has already announced it will offer continuing access to Windows 7 security updates (for a fee, of course) through January 2023, with access through partners and Microsoft corporate account specialists. The real question is how the company will cover small and medium-sized businesses, who are least likely to have partner arrangements and are thus most at risk.

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Simplify licensing.

When I was a little boy, every year I asked Santa for a pony. He never brought one. This suggestion’s probably in the same not-gonna-happen bucket, but I throw it in just because it never hurts to ask.

When Windows 10 was released, I noted that the lineup of editions was refreshingly simple. That, unfortunately, didn’t last long. There was Windows 10 S, which was a brand new edition and then turned into a feature. Three lineups of Microsoft 365 are making the decision matrix even more confusing for IT pros. And with a consumer edition of Microsoft 365 on the calendar for 2019, things are going to get more complicated, not less.

So, for my final wish, I ask Microsoft, please: Keep it simple.

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CISO Podcast: Talking Anti-Phishing Solutions

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Simon Gibson earlier this year published the report, “GigaOm Radar for Phishing Prevention and Detection,” which assessed more than a dozen security solutions focused on detecting and mitigating email-borne threats and vulnerabilities. As Gibson noted in his report, email remains a prime vector for attack, reflecting the strategic role it plays in corporate communications.

Earlier this week, Gibson’s report was a featured topic of discussions on David Spark’s popular CISO Security Vendor Relationship Podcast. In it, Spark interviewed a pair of chief information security officers—Mike Johnson, CISO for SalesForce, and James Dolph, CISO for Guidewire Software—to get their take on the role of anti-phishing solutions.

“I want to first give GigaOm some credit here for really pointing out the need to decide what to do with detections,” Johnson said when asked for his thoughts about selecting an anti-phishing tool. “I think a lot of companies charge into a solution for anti-phishing without thinking about what they are going to do when the thing triggers.”

As Johnson noted, the needs and vulnerabilities of a large organization aligned on Microsoft 365 are very different from those of a smaller outfit working with GSuite. A malicious Excel macro-laden file, for example, poses a credible threat to a Microsoft shop and therefore argues for a detonation solution to detect and neutralize malicious payloads before they can spread and morph. On the other hand, a smaller company is more exposed to business email compromise (BEC) attacks, since spending authority is often spread among many employees in these businesses.

Gibson’s radar report describes both in-line and out-of-band solutions, but Johnson said cloud-aligned infrastructures argue against traditional in-line schemes.

“If you put an in-line solution in front of [Microsoft] 365 or in front of GSuite, you are likely decreasing your reliability, because you’ve now introduced this single point of failure. Google and Microsoft have this massive amount of reliability that is built in,” Johnson said.

So how should IT decision makers go about selecting an anti-phishing solution? Dolph answered that question with a series of questions of his own:

“Does it nail the basics? Does it fit with the technologies we have in place? And then secondarily, is it reliable, is it tunable, is it manageable?” he asked. “Because it can add a lot overhead, especially if you have a small team if these tools are really disruptive to the email flow.”

Dolph concluded by noting that it’s important for solutions to provide insight that can help organizations target their protections, as well as support both training and awareness around threats. Finally, he urged organizations to consider how they can measure the effectiveness of solutions.

“I may look at other solutions in the future and how do I compare those solutions to the benchmark of what we have in place?”

Listen to the Podcast: CISO Podcast

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Phish Fight: Securing Enterprise Communications

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Yes, much of the world may have moved on from email to social media and culturally dubious TikTok dances, yet traditional electronic mail remains a foundation of business communication. And sadly, it remains a prime vector for malware, data leakage, and phishing attacks that can undermine enterprise protections. It doesn’t have to be that way.

In a just released report titled “GigaOm Radar for Phishing Prevention and Detection,” GigaOm Analyst Simon Gibson surveyed more than a dozen enterprise-focused email security solutions. He found a range of approaches to securing communications that often can be fitted together to provide critical, defense-in-depth protection against even determined attackers.

Figure 1. GigaOm Radar for Email Phishing Prevention and Detection

“When evaluating these vendors and their solutions, it is important to consider your own business and workflow,” Gibson writes in the report, stressing the need to deploy solutions that best address your organization’s business workflow and email traffic. “For some it may be preferable to settle on one comprehensive solution, while for others building a best-of-breed architecture from multiple vendors may be preferable.”

In a field of competent solutions, Gibson found that Forcepoint, purchased recently by Raytheon, stood apart thanks to the layered protections provided by its Advanced Classification Engine. Area 1 and Zimperium, meanwhile, are both leaders that exhibit significant momentum, with Area 1 boosted by its recent solution partnership with Virtru, and Zimperium excelling in its deep commitment to mobile message security.

A mobile focus is timely, Gibson says in a video interview for GigaOm. He says companies are “tuning the spigot on” and enabling unprecedented access and reliance on mobile devices, which is creating an urgent need to get ahead of threats.

Gibson’s conclusion in the report? He singles out three things: Defense in depth, awareness of existing patterns and infrastructure, and a healthy respect for the “human factor” that can make security so hard to lock down.

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When Is a DevSecOps Vendor Not a DevSecOps Vendor?

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DevOps’ general aim is to enable a more efficient process for producing software and technology solutions and bringing stakeholders together to speed up delivery. But we know from experience that this inherently creative, outcome-driven approach often forgets about one thing until too late in the process—security. Too often, security is brought into the timeline just before deployment, risking last minute headaches and major delays. The security team is pushed into being the Greek chorus of the process, “ruining everyone’s fun” by demanding changes and slowing things down.

But as we know, in the complex, multi-cloud and containerized environment we find ourselves in, security is becoming more important and challenging than ever. And the costs of security failure are not only measured in slower deployment, but in compliance breaches and reputational damage.

The term “DevSecOps” has been coined to characterize how security needs to be at the heart of the DevOps process. This is in part principle and part tools. As a principle, DevSecOps fits with the concept of “shifting left,” that is, ensuring that security is treated as early as possible in the development process. So far, so simple.

From a tooling perspective, however, things get more complicated, not least because the market has seen a number of platforms marketing themselves as DevSecOps. As we have been writing our Key Criteria report on the subject, we have learned that not all DevSecOps vendors are necessarily DevSecOps vendors. Specifically, we have learned to distinguish capabilities that directly enable the goals of DevSecOps from a process perspective, from those designed to support DevSecOps practices. We could define them as: “Those that do, and those that help.”

This is how to tell the two types of vendor apart and how to use them.

Vendors Enabling DevSecOps: “Tools That Do”

A number of tools work to facilitate the DevSecOps process -– let’s bite the bullet and call them DevSecOps tools. They help teams set out each stage of software development, bringing siloed teams together behind a unified vision that allows fast, high-quality development, with security considerations at its core. DevSecOps tools work across the development process, for example:

  • Create: Help to set and implement policy
  • Develop: Apply guidance to the process and aid its implementation
  • Test: Facilitate and guide security testing procedures
  • Deploy: Provide reports to assure confidence to deploy the application

The key element that sets these tool sets apart is the ability to automate and reduce friction within the development process. They will prompt action, stop a team from moving from one stage to another if the process has not adequately addressed security concerns, and guide the roadmap for the development from start to finish.

Supporting DevSecOps: “Tools That Help”

In this category we place those tools which aid the execution, and monitoring, of good DevSecOps principles. Security scanning and application/infrastructure hardening tools are a key element of these processes: Software composition analysis (SCA) forms a part of the development stage, static/dynamic application security testing (SAST/DAST) is integral to the test stage and runtime app protection (RASP) is a key to the Deploy stage.

Tools like this are a vital part of the security layer of security tooling, especially just before deployment – and they often come with APIs so they can be plugged into the CI/CD process. However, while these capabilities are very important to DevSecOps, they can be seen in more of a supporting role, rather than being DevSecOps tools per se.

DevSecOps-washing is not a good idea for the enterprise

While one might argue that security should never have been shifted right, DevSecOps exists to ensure that security best practices take place across the development lifecycle. A corollary exists to the idea of “tools that help,” namely that organizations implementing these tools are not “doing DevSecOps,” any more than vendors providing these tools are DevSecOps vendors.

The only way to “do” DevSecOps is to fully embrace security at a process management and governance level: This means assessing risk, defining policy, setting review gates, and disallowing progress for insecure deliverables. Organizations that embrace DevSecOps can get help from what we are calling DevSecOps tools, as well as from scanning and hardening tools that help support its goals.

At the end of the day, all security and governance boils down to risk: If you buy a scanning tool so you can check a box that says “DevSecOps,” you are potentially adding to your risk posture, rather than mitigating it. So, get your DevSecOps strategy fixed first, then consider how you can add automation, visibility, and control using “tools that do,” as well as benefit from “tools that help.”

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