As businesses race to adopt conditional access as part of their zero trust security strategy, many underestimate the complexity of getting it right. Conditional access is one of the most powerful tools for reducing risk in today’s hybrid, perimeterless environments — but if misconfigured, it can leave critical gaps or frustrate end-users. Whether you’re just getting started or refining your approach, it’s essential to recognize where most organizations tend to go wrong. Below are five of the most common conditional access mistakes — and how your team can avoid them.

1. Overly Permissive Access Policies

   The Mistake: In an effort to simplify implementation or reduce user friction, many organizations take a “one-size-fits-all” approach to access policies. They apply the same level of access to all users, regardless of risk level, role, or context, often allowing too much access by default. Why It’s a Problem: When everyone has the same access, your most privileged users — finance, IT admins, executive leadership — are often overexposed. Attackers know this and will target those users first. Flat, permissive access policies effectively negate the benefits of conditional access by treating every login as equally trustworthy. How to Avoid It: Design policies around least privilege and risk-based access. Use user roles, groups, and job functions to define granular access. Consider stronger requirements (e.g., multi-factor authentication or device compliance checks) for high-privilege accounts. Align access decisions with risk, not convenience.

2. Ignoring Device Trustworthiness

   The Mistake: Many conditional access deployments focus entirely on user identity while ignoring the device being used. If a user has valid credentials and passes authentication, access is granted — regardless of whether they’re logging in from a corporate laptop or a personal tablet with outdated software. Why It’s a Problem: A compromised or non-compliant device can undermine even the strongest authentication. Malware, keyloggers, or a lack of encryption can put sensitive data at risk, especially in BYOD environments where IT lacks full visibility. How to Avoid It: Incorporate device posture checks into your conditional access policies. Evaluate whether the device is:
   • Running an approved OS
   • Patched and up to date
   • Encrypted
   • Protected by antivirus or EDR
   • Managed by your organization (via MDM/UEM)
   Based on this information, allow or restrict access, or route the device to a self-remediation flow. Device trust should be a non-negotiable part of zero trust access control.

3. Failing to Account for Cloud and SaaS Access

   The Mistake: Traditional access controls focused on VPNs and on-premise networks. Some organizations treat conditional access the same way, failing to extend policies to cloud apps and SaaS platforms, or applying only basic rules like “allow from internal IP addresses.” Why It’s a Problem: Modern work happens in the cloud — from Microsoft 365 to Salesforce, Dropbox, Zoom, and countless others. If conditional access policies don’t govern these platforms, you create blind spots where threat actors can operate undetected, often using stolen credentials. How to Avoid It: Implement conditional access that integrates directly with cloud identity providers (e.g., Azure AD, Okta, Google Workspace) and supports enforcement across both on-premise and cloud environments. Apply the same risk-based, context-aware policies to SaaS access as you would for internal systems. This includes enforcing policies such as:
   • Block access from unknown or unmanaged devices
   • Require MFA outside of known geographies
   • Limit download or sharing capabilities for sensitive content

4. Neglecting Guest and Contractor Devices

   The Mistake: Organizations often overlook non-employee users such as contractors, vendors, partners, and guests, assuming these accounts are “temporary” or too difficult to manage. As a result, these users may receive access without proper policy enforcement or device checks. Why It’s a Problem: Third-party accounts are among the most common causes of data breaches. Contractors frequently use unmanaged or shared devices and may not receive the same training or oversight as full-time staff. Giving them unrestricted access introduces serious risk. How to Avoid It: Treat third-party identities and devices with the same scrutiny as internal users. Use your NAC or conditional access solution to:
   • Restrict guest access to internet-only or isolated segments
   • Assign contractors to limited access roles
   • Enforce device compliance checks or MFA
   • Monitor and automatically expire access when projects end
   If your tools don’t support these controls natively, it’s time to consider more flexible, cloud-native solutions that make managing guests and contractors easier — and safer.

5. Not Testing Policies Before Deployment

   The Mistake: Conditional access policies are rolled out without proper testing, leading to broken access, frustrated users, or worse, unintended exposure. Some organizations rely on default policy templates or push policies live without staging environments. Why It’s a Problem: An overly strict policy can block legitimate users and interrupt business. A lax policy can let unauthorized users slip through unnoticed. Without testing, it’s nearly impossible to predict the impact of a new rule across your environment. How to Avoid It: Always test conditional access policies in report-only mode or staging environments first. Use simulations to identify who would be affected, which devices might be blocked, and what workflows need refinement. Gather feedback from pilot groups and adjust before broader rollout. Also, schedule regular reviews and updates — especially as your workforce, applications, or threat landscape changes.

Get Conditional Access Right — the First Time

Conditional access is one of the most effective tools for enforcing zero trust, but only when implemented with precision. By avoiding these common mistakes — and leveraging the right platform — you can protect sensitive systems, support hybrid work, and improve security without sacrificing user experience.