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Securing Privileged Access with Azure AD (Part 3) – Hybrid Scenarios

While many organisations are well on the journey to exclusively operating in the cloud, the reality is that most companies operate in a hybrid state for an extended period of time. As such, we cannot always apply all of our Privileged Access effort on securing the only the cloud. In this post, I’ll walk you through three simple methods which allow you to extend Azure AD capability into an on-premise environment, with the support of key “legacy” technology. If you’re just joining us for this series, head over to part one to learn about strategy, or part two for Azure AD Basics!

1. Reducing privileged access on premise with PIM

One of the challenges that many organisations perceive with PIM, is that it doesn’t extend to on-premise services. This perception is wrong – Yes, PIM itself doesn’t have native capability for on-premise, but it is extremely simple to consume PIM groups within an on premise environment. This can be done in two ways.

  1. Custom group write-back using Microsoft Identity Manager

2. Automation write-back using a script, automation account or logic-app.

Both of these options require a pragmatic approach to deployment tradeoffs. For MIM group write-back, precise time bound access doesn’t really work. MIM generally syncs on a pre defined schedule, so you would need to configure PIM lifespans to cater for this, leaving some wriggle room on either side of the PIM window. Some companies prefer not to run custom built integration, so scripts which do the sync on our own schedule are avoided.

Thankfully, the community has put some excellent effort into this space, with by far the best example of this being the goodworkaround write-back script.

Sync Privileged Access from Azure to Active Directory with custom scripts.
Visualisation of the Hybrid scenario. Source: github.com

2. Forcing MFA for administrative access using Windows Admin Center

Regardless of how you choose to manage group membership for administrative access, sometimes the simplest security control you can apply to access is the best. MFA is by far, the most effective control you can apply to admin logins.

But how to achieve this? Unfortunately, Windows Server still doesn’t include native support for Azure AD MFA inside the RDP UI (Some secondary products like Duo or Okta have solutions for this). Sure this is a bit of a bummer, but let’s be honest; Direct RDP access to a server should NOT be required in the majority of scenarios. This is for two reasons;

  • Infrastructure as Code – If you’re able to configure a server to be replaced by a pipeline, you should. Maintenance and incident remediation is a lot easier when you can simply replace the infrastructure at the click of a button, without ever logging in.
  • Remote shell – You can do pretty much anything from the command line or PowerShell these days. In my opinion, RDP by default isn’t worth the security hassle. Restrict RDP usage and move to the CLI.

If you’re not comfortable in this space, or would just like an excellent solution which lets you monitor and configure multiple servers, Microsoft provides a world class solution for remote management, Windows Admin Center (WAC). In my opinion, this is highly under-utilised and a great addition to any IT Pros toolkit.

Thankfully, Windows Admin Center has native support for Azure AD authentication. Using Conditional access, you can then apply MFA to admin access.

Managing server Privileged Access with Windows Admin Centre

Configuring this within WAC is a straight forward task, with the settings for Azure AD Authentication available to configure under the “Settings > Access” blade:

Once enabled, you will be able to locate an Admin Center application within your Azure AD Tenant, which you can utilise to scope a targeted Conditional Access policy.



For this capability to truly be effective, you can also combine the WAC solution with an RD Gateway for RDP scenarios. Because RD Gateways operate using a Connection Authorisation Policy with NPS, you can quickly apply MFA to user sessions with the NPS extension. Be warned, this does add a small configuration overhead and occasionally a “double auth” scenario.

3. Extending Azure AD to networking infrastructure using SSO Integration or Network Policy Server

A lot of focus is generally exerted by IT teams on securing server infrastructure. But what about the network? As discussed in our strategy post, a holistic approach to privileged access includes all the solutions you manage. As the network carries all traffic for your solutions, some security practitioners will argue that securing this access is more important than securing the infrastructure!

Networking infrastructure being so diverse, you could generally enhance network privileged access security in two distinct manners.

  1. Integrate Azure AD to centralised control plane. This will require standardisation of access through a network vendor solution.
  2. Integrate networking devices to AAD via Radius. This requires support of specific radius protocols on your network devices.

Our first option in my opinion is the best one. Nearly every networking vendor these days provides a secure access control mechanism, Cisco has Identity Service Engine, Aruba uses ClearPass, Palo Alto uses Panorama, the list goes on for miles. Because these native tools integrate directly with access control for your networking appliances it can be an extremely quick win to apply SSO via Azure AD and MFA via Conditional Access. You can then combine this with services like Privileged Identity Management (PIM) to manage access through approval flows and group claims. Each of your networking vendors will provide documentation for this:

The second option works in privileged access scenarios where you don’t have a centralised identity service. Provided you can use the correct radius protocols, admins can configure the Azure MFA extension for NPS, with radius integration enabling MFA for your networking kit! In the below example, I use this to apply MFA to a SSH management interface for a Palo Alto firewall.

Managing Privileged Access for SSH using Radius and the MFA Extension

Up Next

Using the above three techniques, you very quickly end up with a potential architecture that might look like this.

Thanks for sticking with me through this weeks guidance on Hybrid Scenarios If you’re after some more Privileged Access information, have a read of my AAD Basics guidance, or stay tuned for more info on what can be done using Azure AD, including some tips and techniques to help you stay in control. Topics this series is covering are:

  1. Strategy & Planning
  2. Azure AD Basics
  3. Hybrid Scenarios (This Post)
  4. Zero Trust
  5. Protecting Identity
  6. Staying in Control

Until next time, stay cloudy!

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