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Microsoft 365 Security Assessment Part 1

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Matthew Levy
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As a Microsoft 365 certified Security Administrator, and Microsoft certified Azure Security Engineer I have recently done a number of Microsoft 365 security assessments. Some of them have been post-breach assessments. A lot of companies had to enable remote workers in a hurry at the start of the COVID-19 pandemic, and as a result have realized security configuration and protection is more critical than ever.

After the start of the pandemic, Microsoft released some guidance for enabling remote work securely – “Work remotely, stay secure—guidance for CISOs

That blog post lists a bunch of products that Microsoft offers to help, but they are not listed in a step by step guide as to what to tackle first and how to move on to the next. What people are looking for is a partner that can give them recommendations or a list of configuration steps to secure their environments.

So, in this post, I aim to provide an actionable checklist for Microsoft 365 customers based on the experiences I’ve had doing security assessments.

With that, let’s get started on securing your environment:

Start with Azure Active Directory (Azure AD)

  • Register everyone for Multi-Factor Authentication (MFA)

Picture1-Oct-27-2020-08-28-39-03-PMFigure 1: Multiple verification options

Multi-factor authentication is a process where a user is prompted during the sign-in process for an additional form of identification, such as to enter a code on their cell phone or to provide a fingerprint scan. An example is shown in Figure 1: Multiple verification options

Passwords are an insecure vector, vulnerable to attack. If the password is weak or has been exposed elsewhere, is it really the user signing in with the username and password, or is it an attacker? Azure Multi-Factor Authentication works by requiring two or more of the following authentication methods:

  • Something you know, typically a password.
  • Something you have, such as a trusted device that is not easily duplicated, like a phone or hardware key.
  • Something you are - biometrics like a fingerprint or face scan.

Everyone should register multiple verification methods, so that you can require MFA anytime a sign-in is deemed risky, either because you decide or the machine learning intelligence that Microsoft has decided it’s risky.

How-to-guide: Plan Azure MFA deployment

  • Enable Self Service Password reset (SSPR)

Self Service Password Reset (SSPR) is a feature available in AAD Premium P1 and above. It allows users to reset their passwords when they have forgotten the current password. The service is secure in that users must provide verification methods to prove they are who they say they are before they are able to reset their passwords.

Picture1-Oct-27-2020-08-29-21-91-PMFigure 2: Self Service Password Reset (SSPR)

Tutorial: Enable Self Service Password Reset

  • Enable the combined SSPR and MFA registration experience

When you enable this combined registration experience (shown in Figure 3: Combined security registration experience), users need only select their registration information once to enable both MFA and SSPR features.

Picture1-Oct-27-2020-08-29-54-77-PMFigure 3: Combined security registration experience

Enable the combined security information registration

  • If you are syncing identities from on-premises AD DS, enable Password Hash Sync

Password hash synchronization is an extension to the directory synchronization feature implemented by Azure AD Connect sync.

Picture1-Oct-27-2020-08-30-23-79-PMFigure 4: AAD Connect Optional features

You can enable this optional feature in the Azure AD Connect wizard shown in Figure 4: AAD Connect Optional features. This will allow users to sign in to Azure AD services like Microsoft 365 by using the same password they use to sign in to your on-premises Active Directory instance. In Figure 5: Signing-in to SaaS apps using password from on-premises you can see how this makes things simpler for the user.

Picture1-Oct-27-2020-08-31-02-68-PMFigure 5: Signing-in to SaaS apps using password from on-premises

Password Hash Sync also gives you the ability to leverage password protection functionality, such as breach replay protection and leaked credential reports.

Tutorial: Enable Password Hash Sync (PHS)

  • Configure Azure AD Password Protection and if you are syncing from on-premises, enable password protection on Windows Server Active Directory.

Azure AD Password Protection detects, and blocks known weak passwords and their variants, and can also block additional weak terms that are specific to your company using custom banned passwords as shown in Figure 6: Custom banned passwords.

Picture1-Oct-27-2020-08-31-31-45-PMFigure 6: Custom banned passwords

With Azure AD Password Protection, default global banned password lists are automatically applied to all users in an Azure AD tenant. You can define entries in a custom banned password list. When users change or reset their passwords, these banned password lists are checked to enforce the use of strong passwords as shown in Figure 7: Password blocked by banned password list.

Picture1-Oct-27-2020-08-32-03-32-PMFigure 7: Password blocked by banned password list

Tutorial: Configure banned passwords for AAD

  • Configure custom company branding.

Adding custom branding not only personalizes the sign-in pages to match your corporate identity but is also vital in securing your users against phishing and other identity attacks. Users should become accustomed to seeing the custom company branding and sign-in text. When a sign-in request doesn’t present the correct branding and sign-in texts, users should be suspicious of requests for supplying log-in credentials. This type of awareness needs to be communicated to employees.

Picture1-Oct-27-2020-08-32-35-68-PMFigure 8: Custom image requirements for company branding

  • Consider the merits of restricting app registration and the admin consent workflow

Before an application can access your organization's data, a user must grant the application permissions to do so. In Figure 9: User consent for applications options you can see that different permissions allow different levels of access. By default, all users can consent to applications for permissions that don't require administrator consent.

Picture1-Oct-27-2020-08-34-21-99-PMFigure 9: User consent for applications options

To reduce the risk of malicious applications attempting to trick users into granting them access to your organization's data, Microsoft recommends that you allow user consent only for applications that have been published by a verified publisher.

In addition, if you restrict users from consenting to apps, users will see a generic error message suggesting they contact the admin. Not all users know who to contact in this instance, so it’s advisable to enable the admin consent workflow feature which is currently in public preview.

The system then sends a notification to the delegated application admin user via email and the end user requesting the app is show a notification as shown in Figure 10: Admin request sent notification

Picture1-Oct-27-2020-08-34-56-03-PMFigure 10: Admin request sent notification

See more information about how the Admin consent workflow notifies an admin that a user has requested an app, in my blog post "App admin consent workflow – What is looks like in action"

  • If you don’t have Azure AD Premium (AAD P1 or AAD P2), Enable Security Defaults.

Security defaults protect organizations with one master policy. Customers with the free or Office 365 versions of Azure AD are encouraged to use security defaults because they don’t have the granularity of Conditional Access policies. Security defaults essentially enable five policies in the background that protect the tenant:

  • Requiring all users to register for Azure Multi-Factor Authentication.
  • Requiring administrators to perform multi-factor authentication.
  • Blocking legacy authentication protocols.
  • Requiring users to perform multi-factor authentication when necessary.
  • Protecting privileged activities like access to the Azure portal.

Picture1-Oct-27-2020-08-35-24-59-PMFigure 11: Security defaults master switch

Security defaults gives you a balance of security and productivity without you having to create the security policies yourself.

Enabling security defaults

  • Enable passwordless phone sign-in

MFA is a great way to secure your organization, but users often get frustrated with the additional security layer on top of having to remember complex passwords. Passwordless authentication is more convenient because the password is removed and replaced with something you have, plus something you are or something you know.

You may already be using the Microsoft Authenticator App as a convenient multi-factor authentication option in addition to a password. You can also use the Authenticator App as a passwordless option.

Picture1-Oct-27-2020-08-35-57-15-PMFigure 12: Signing in without a password

Users can sign in by getting a notification to their phone, matching a number displayed on the screen (Figure 12: Signing in without a password) to the one on their phone, and then using their biometric (touch or face) or PIN to confirm.

Enable passwordless phone sign-in

  • Enable Azure AD Identity Protection

Azure AD Identity Protection is a security module of Azure Active Directory that provides a consolidated view into risk detections and potential vulnerabilities affecting an organization’s identities.

Identity Protection uses the learnings Microsoft has acquired from their position in organizations with Azure AD, the consumer space with Microsoft Accounts, and in gaming with Xbox to protect your users. Microsoft analyses 6.5 trillion signals per day to identify and protect customers from threats.

The signals generated by and fed to Identity Protection, can be further fed into tools like Conditional Access to make access decisions.

  • Create conditional access policies

Conditional Access is the tool used by Azure Active Directory to bring signals together, to make decisions, and enforce organizational policies.

Picture1-Oct-27-2020-08-36-24-80-PMFigure 13: Conditional Access signals and actions

Conditional Access is at the heart of the identity driven control plane. Conditional Access policies at their simplest are if-then statements.

Multiple conditions can be combined to create fine-grained and specific Conditional Access policies.

For example, when accessing a sensitive application, an administrator may factor sign-in risk information from Azure Identity Protection and require more verification from the user.

If a user wants to access a resource, then they must complete an action. Example: A payroll manager wants to access the payroll application and is required to perform multi-factor authentication to access it.

Below are some common Conditional Access policies which many organizations are applying as a standard set of policies.

  • Requiring multi-factor authentication for users with administrative roles
  • Requiring multi-factor authentication for Azure management tasks
  • Blocking sign-ins for users attempting to use legacy authentication protocols
  • Requiring trusted locations for Azure Multi-Factor Authentication registration
  • Blocking or granting access from specific locations
  • Blocking risky sign-in behaviours
  • Requiring organization-managed devices for specific applications

Check out this blog post by Daniel Chronlund where he lists 13 conditional access policies, he believes will meet the needs of most organizations. Azure AD Conditional Access Policy Design Baseline – Daniel Chronlund Cloud Tech Blog (

When it comes to Microsoft 365 security tips, there’s a lot to cover. This week we walked through some actionable steps to help you manage Azure Active Directory. Keep an eye out for part 2 next week where I’ll dive into some security tips for the Microsoft 365 Admin Center!

Active Directory Monitoring and Reporting

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