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Legacy Servers Are a Cyber Insurance Pre-existing Condition

Written by David Worthington on March 1, 2022

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Ransomware is a a year racket and attacks against small and medium-sized enterprises (SMEs) are , costing companies between on average. The insurance industry is stepping in with cyber insurance policies tailored to help SMEs recover; but, as with any plan, there鈥檚 an underwriting process to avoid adverse selection. Insurance companies aren鈥檛 in business to just give money away and don鈥檛 want too many 鈥渟ick鈥 clients.

Insurers determine whether an SME is worth the risk by assessing where there are sufficient security controls and patching strategies in place. They鈥檝e recently keyed in on several high-profile software vulnerabilities related to Microsoft Exchange Server, for example. Exchange鈥檚 presence, and the absence of critical security updates for it, are being used as .

The assessment of risk doesn鈥檛 begin or end with Exchange. A client asked me to help her fill out an application for cyber insurance that services the legal industry and questions ranged from the usage of technical controls such as multi-factor authentication (MFA) and email security to least privilege computing. However, several legacy products and solutions were also explicitly called out:

Don鈥檛 just take our word for it 鈥 here it is, in black and white:

Common cyber insurance questions, including questions about running Microsoft Windows 7 and Microsoft Windows Server 2008.
Attribution: CyberLock Lawyer

Many IT admins would publicly roll their eyes at the notion that any SME would be using unsupported software, but those of us who have been out in the field know what鈥檚 hidden underneath the covers. Why else would insurers be asking?  If administrative overhead is inherent to operate legacy, on-premise infrastructure in any organization, and if doing the same old thing is a 鈥減re-existing condition,鈥 why not change? Simply put, many companies feel they don鈥檛 have the resources in their budget to update old server racks or to locate and hire qualified people to do this. 

To that I say, it all boils down to this question: Is it worth the risk to maintain all of that legacy, or is it possible to think differently, accomplish more, and become a (insurer-friendly) security and compliance hero?

Risk Transference 

Migrating to a cloud service is risk transference, and we鈥檇 argue it鈥檚 an effective way to reduce vulnerabilities that cyber insurers would approve of. You鈥檙e placing trust in a SaaS provider to have a mature secure development lifecycle (SDLC), a security operations center (SOC), and a team that has experience and technical certifications that an SME couldn鈥檛 afford to implement.

IT admins can use 探花大神 for their identity and access management (IAM) infrastructure, with confidence. 探花大神 has completed a SOC Type 2 examination for its directory platform and follows these security best practices. You can read more about why you should trust us here.

In all fairness, Microsoft has also invested heavily in security (I had the pleasure of working with some terrific people on its security team). However, as noted by , Microsoft can鈥檛 be both the firefighter and the arsonist. Its legacy on-premise products are a wellspring of security vulnerabilities and products that are beyond end-of-life are compromised and insecure.

That鈥檚 true even for server products that are within the support lifecycle. For instance, I had to decommission a domain controller (DC) that had been running Remote Desktop Protocol and was open to the web. That meant rebuilding the DC and deploying a dedicated server for RDP. There were several hidden costs to this endeavor, like ensuring that the server rack and our server virtualization suite (and staff who had to be certified to use it) were capable of handling those changes. Costs add up, quickly.

Today鈥檚 IT environments require a Zero Trust security posture and many industries are governed by regulations and compliance policies, or soon will be, that have specific requirements that must be met. This calls for systems that are up to the challenge, but manageable enough, so that SMEs don鈥檛 have to buy a fully loaded Porsche for a cruise down Main Street.

探花大神 is designed to support the requirements of SMEs to manage the user lifecycle across all devices, regardless of the OS, and to connect to more things securely. Zero Trust IAM and compliance features such as patch management tools are exactly what cyber insurers are looking for. 

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The IT Manager鈥檚 Guide to Data Compliance Hygiene

How to ace your audit

Do More with Easy Zero Trust and Compliance 

Specifically, 探花大神 enables Zero Trust through cloud directory policies, unified device management, , single sign-on (SSO) for all apps, and free multi-factor authentication (MFA). The user鈥檚 journey begins with a strong password on a device that鈥檚 managed by policies; and policies can become conditions that must be met before access is granted to IT resources. Conditions can include rules such as 鈥渋s this device patched?鈥, and 探花大神 provides cross-OS patching and device management to support compliance with those rules. We鈥檙e continuing to expand upon those patching capabilities and provide for easier reporting.

Compliance is another consideration for insurers. The 探花大神 platform is audit-ready with a device panel highlights tab that consolidates all pertinent system, access, and device information into a single view. 探花大神 enables its users to treat compliance as a process, not a product. Easy compliance is part of the domainless enterprise, which empowers IT admins versus the on-premise software that creates the attack surface area that cyber insurance is, ironically, intended to safeguard against. It鈥檚 better to be prepared for the future than have to take corrective actions.

If managing legacy servers would risk your organization being denied access to cyber insurance, now is the time to seriously consider moving on to a more modern directory and IAM infrastructure.

Try 探花大神

探花大神 is a cloud directory with advanced IAM capabilities throughout its cloud platform, securely connecting you to more resources than on-premise solutions at a lower cost. It鈥檚 for up to 10 users/devices with complimentary premium support over the initial 10 days.

David Worthington

I'm the 探花大神 Champion for Product, Security. 探花大神 and Microsoft certified, security analyst, a one-time tech journalist, and former IT director.

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