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Chris Stegh /

Cyber Insurance Requiring MFA *Everywhere*

Cyber insurance providers are tightening their requirements for Multi-factor Authentication. For starters, they are being more verbose about the systems and services on which MFA is enabled. They’re making what had been a very broad question into a set of discrete questions. Essentially, what was “Do you have MFA enabled?” is now “Do you have MFA enabled on x, y, and z? 

This blog outlines some of the systems and services commonly asked about in insurance questionnaires. It also suggests ways to address the scenarios, possibly with identity/MFA services that organizations already own. 

Summary of MFA Requirements: 

In summary, insurers’ questionnaires are now asking about MFA for: 

  1. All employees when accessing email through a website or cloud based service  
  2. All remote access to the network provided to employees, contractors, and 3rd party service providers (both via web and VPN) 
  3. All internal & remote admin access to directory services (active directory, LDAP, etc.) 
  4. All internal & remote admin access to network backup environments.  
  5. All internal & remote admin access to network infrastructure (firewalls, routers, switches, etc.).  
  6. All internal & remote admin access to the organization’s endpoints/servers. 

Can Microsoft’s Identity services meet all these needs? 

Mostly, but not without some effort. The table below details some of the systems and services about which insurance questionnaires commonly ask. Many scenarios can be covered by Microsoft identity services, many of which organizations already own. 

How to use this chart 

There are two sections, the first for administrators and the second for end-users. On the left hand side, you'll see the use cases where Multifactor Authentication will be required. In subsequent columns, we articulate if Microsoft has a first party solution for that requirement. The Licensing column articulates the licensing needed to enable the solution, while the final / notes column points out some key information. The list is not exhaustive but attempts to capture the insurers’ current requirements. 

Admin Access

System or Service

MSFT Service/Tool 

Licensing Required 


M365 & Azure Admin  

Azure AD MFA 

Free tier of Azure Active Directory  

  • Part of automatic Security Defaults. 
  • Allows authenticated login, 24x7 (no conditions). 

M365 & Azure Admin 

Privileged Identity Management (provides Just-in-Time Access, blocking otherwise) 

Azure AD P2 

License needed for every admin, but not every user 

Admin (RDP) access to VMs in Azure  

Hello for Business on Windows 10 1809 and later 



VMs on Windows Server 2019 Datacenter and later 


Azure AD Free or paid 

Also consider Defender for Cloud which provides Just in Time access to port 3389 and includes Cloud Security Posture Management (CSPM) and Cloud Workload Protection Platform (CWPP) capabilities ($15/server/mo) 

Admin access to on-premises Servers 


(can apply to backup services and network infrastructure (firewalls, routers, switches, etc.) that support AD\AAD authentication or RADIUS) 

  • Remote Desktop Services (RDS) infrastructure 
  • Azure AD MFA License 
  • Windows Server software 
  • Network Policy and Access Services (NPS) role 
  • Azure Active Directory synched with on-premises Active Directory 
  • Azure Active Directory GUID ID 


See Integrate RDG with Azure AD MFA NPS extension - Azure Active Directory Kic- Microsoft Entra | Microsoft Docs 


Use Azure AD Multi-Factor Authentication with NPS - Azure Active Directory - Microsoft Entra | Microsoft Docs 


An (unofficial) setup using AzureAD/FIDO Keys, Remote Credential Guard and primarily Active Directory SCRIL 


Third-party options exist as well 


Local (console) login to an on-premises Windows Server 



FIDO2 on Windows Server 2019





User Access to M365 + Cloud Resources 

System or Service 

MSFT Service/Tool 

Licensing Required 


M365 & Exchange Online email user access 

Azure AD MFA 

Any Office 365 plan provides basic MFA 

  • Insurers have asked about “MFA for Remote Access to email (through a website or cloud service)” 
  • With basic (free) MFA, prompts are more frequent, potentially leading to fatigue. 

M365 user access with Conditional Access (CA) 

Azure AD MFA with CA 

Azure AD P1 

Once config’d, allow/block decisions can include location, app, device, and Azure AD-join status. 

M365 user access with ML/AI risk decisions 

Azure AD Identity Protection  

Azure AD P2 

Once active, allow/block decisions include risky behavior assessments (i.e. impossible travel) 

User access to 3rd party SaaS 

Azure AD MFA 

Azure AD Free (for up to 10 SaaS apps, no SLA) 

Azure AD P1 (for unlimited apps w/ SLA) 

Allows user to login once, and when config’d, Azure AD enables SSO to 3000+ web apps 

Azure Virtual Desktop 

Azure AD MFA 

Azure AD P1 for Conditional Access 

How often a user is prompted to re-authenticate depends on AAD session lifetime configuration settings 


User Access to on-Prem Resources 

System or Service 

MSFT Service/Tool 

Licensing Required 


Remote user access to VPN 

Azure AD MFA 

Azure AD Free 

Examples: Cisco Anyconnect 

Palo Alto GlobalConnect 

Remote user access to app servers on premises 

Azure AD App Proxy 


Azure AD P1 or P2 

When config’d, allows Communicator app to prompt for response prior to granting access to ERPs, web servers, etc..  

Requires deployment of AAD AppProxy on a VM. 

User access to Terminal Server 

(i.e. RDP into a remote machine) 

  • Remote Desktop Services (RDS) infrastructure (on prem or in Azure)  
  • Windows Server software 
  • Network Policy and Access Services (NPS) role 
  • Azure Active Directory synched with on-premises Active Directory 
  • Azure Active Directory GUID ID 

Azure AD P1 (or higher) License 


See Integrate RDG with Azure AD MFA NPS extension - Azure Active Directory - Microsoft Entra | Microsoft Docs 


Third-party solutions also available  




  1. This list and set of solutions is not completely exhaustive, but it’s meant to provide a checklist and guidance for your next cyber insurance renewal period.
    1. Two things that are not (yet) being as discreetly defined: If remote access is prohibited to on-premises devices by policy or IP restriction, MFA may be excluded on those devices (but check with the insurer).
    2. Alternatively, if admin access is only allowed through a local jump-box computer that does have MFA required, that may circumvent the need to have MFA on the end-server, but again, have the Insurance company weigh in. 
  2. Start with the biggest attack surface (i.e. users on email being phished) quickly followed by protecting the crown jewels (AD Domain controllers and critical business services).
  3. With North Carolina and other states starting to outlaw (governmental) organizations from paying ransomware pirates, these practices are simply good for business anyway.
  4. Since many of these changes involve a user experience change:
    1. Pilot first (making sure your “break glass” accounts are safe)
    2. Ensure you’re educating users about what will be different, including MFA in the overall cyber training program. 
  5.  Several details / decisions can improve security and/or user friction, such as: 
    1. Addressing time to live (TTL) for MFA without requiring re-authentication
    2. Routing remote traffic via VPN connection or by using spilt tunneling?
    3. Developing a process to quickly disable MFA in case a device is lost? 

Work with our team of Cloud Computing Consultants who have done this so many times they know all of the “minefields” to prevent missteps.