Exploring Conditional Access Bypasses in Microsoft Entra ID

Swiss cheese model applied to identity security

Conditional Access is the backbone of Zero Trust in Microsoft Entra ID, yet real world attacks increasingly demonstrate how it can be bypassed. From device and token abuse to built in exclusions and misunderstood session controls, attackers exploit gaps that many organisations assume are protected.

Triggered by Microsoft’s upcoming change in February 2026, where session revocation will finally behave as expected during incident response, this blog analyses observed Conditional Access bypass techniques from real incidents in 2024 and 2025. More importantly, it explains why a strong security baseline is essential to compensate for what Conditional Access was never designed to solve alone.

Require Risk Remediation: The Game-Changer for Conditional Access Policies

Interian | Securing Insights

Discover the game-changing 'Require Risk Remediation' control in Microsoft Entra Conditional Access. This preview feature simplifies risk management by handling both password and passwordless users in one policy, reducing complexity and misconfigurations. Get a step-by-step guide, real-world benefits, and pragmatic insights into its limitations for enhanced security.

Step-by-Step: Build a Copilot Agent for Smarter Intune Alerts in 15 Minutes

Interian | Securing Insights

Every IT professional knows the struggle: an Intune notification pings with a vague error code or cryptic alert about a device compliance issue, failed update, or potential security threat. You're left scratching your head, wondering, "What does this even mean?" These unclear messages can bury critical issues, like non-compliant devices or malware risks, in a flood of noise. Imagine if those alerts came with clear, human-readable explanations and actionable steps.

Microsoft Dumps OTP Authentication for SharePoint Online Sharing with Entra ID B2B

Interian | Securing Insights

Microsoft is phasing out One-Time Passcode (OTP) authentication for SharePoint Online and OneDrive external sharing, replacing it with Entra ID B2B Collaboration, effective July 1, 2025 (MC1089315). Legacy OTP links will stop working, requiring users to re-share content to restore access for external collaborators, who must also register for mandatory MFA. Prepare now by notifying users, updating documentation, auditing shared content, and ensuring Entra ID B2B settings are configured. This shift enhances security but demands proactive planning to avoid disruptions.

New Outlook Feature: Managing Shared Mailboxes as Accounts

Interian | Securing Insights

Microsoft is enhancing shared mailbox management in Outlook for Windows, rolling out from May to August 2025. Users with Full Access can now add shared mailboxes as accounts to manage settings like Rules and Signatures directly. No admin action is needed, but preparation can ensure a smooth transition. Learn how this update impacts your organization and how to prepare.