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However, there are few things to note about the cloud authentication methods listed above.

Most of these applications are accessible from the Internet and regularly targeted by adversaries.

Oktas security team sees countless intrusion attempts across its customer base, including phishing, password spraying, KnockKnock, and brute-force attacks.

They continuously monitor and rapidly respond to these attacks to protect customer tenants and the Okta service.

The most commonly targeted application for these attacks is Office 365, a cloud business productivity service developed by Microsoft.

However, Office 365 uses several authentication methods and access protocols, including options that do not support MFA in their authentication flow.

It has become increasingly common for attackers to explore these options to compromise business email accounts.

This information is based on internal research performed by the Okta security team and does not constitute a replacement for Okta documentation addressing Office 365 configuration for Okta.

It has proven ineffective and is not recommended for the modern IT environments especially when authentication flows are exposed to the internet as is the case for Office 365.

Modern Authentication helps secure Office 365 resources using multi-factor authentication, certificate-based authentication, and SAML-based logins (such as federation with Okta), for a true single sign-on experience.

In the context of this document, the term Access Protocol indicates the protocols such as POP, IMAP, Exchange ActiveSync, Exchange Web Services (EWS), MAPI and PowerShell.

In the context of authentication, these protocols fall into two categories: Access Protocols.

The email provides information about the timestamp, location, and device information, such as IP Address and user agent (OS versionbrowser).

However, with Office 365 client access policies, the access decision can also be implemented based on client type, such as web browser, modern auth or legacy auth clients.

For more details refer to Getting Started with Office 365 Client Access Policy.

Email clients use a combination consisting of one of each of the two attributes to access Office 365 email.

Table 1 summarizes the list of Office 365 access protocols and the authentication methods they support.

Figure 1 below shows the Office 365 access matrix based on access protocols and authentication methods listed in Table 1.

Doing so for every Office 365 login may not always be possible because of the following limitations.

Protocols like POP and IMAP only support basic authentication and hence cannot enforce MFA in their authentication flow.

For example, Outlook clients can default to Basic Authentication when by modifying registry on Windows machines.

Therefore, even if Modern Authentication is enabled on an Office 365 tenant, mail clients can still access it using Basic Authentication.

The Expected BehaviorChanges section below addresses the trade-offs that must be made to enforce MFA for Office 365.

Azure AD supports two main methods for configuring user authentication.

Outlook For Mac Enable New Adal For Exchange Online Tenan