Making the Shift to Passwordless Seamless: Overcoming Objections and Hurdles

Passwords have been the foundation of digital security for decades, but today’s threat landscape has outpaced their effectiveness. Due to resets and lockouts, IT staff are overloaded, and they remain the most popular entry point for phishing, credential theft, and brute-force attacks. Organizations are using secure, scalable authentication systems. PKI-based certificates are non-phishable, device-bound, and cross-platform, making them the most reliable. Biometrics provide a straightforward interface that uses PKI-secured device credentials, while adaptive authentication adds policy-based intelligence. These methods help organisations switch to passwordless security and sustain it.

However, organizations might find that becoming passwordless is not as simple as it appears. Legacy systems, regulatory constraints, and operational complexity derail efforts if not handled promptly. The momentum for passwordless adoption is growing, but real-world challenges slow the progress. Understanding these challenges is essential for establishing safe, long-term solutions.

Why Passwordless is the Future

The password originated in the 1960s at MIT, when researchers wanted a mechanism to keep individual information private on shared computers. Back then, a few characters were sufficient. Fast forward six decades, and we now rely on passwords to protect billions of accounts across crucial networks around the world, a responsibility they were never designed to bear. They are phishable, easily reused between systems, and difficult to reset or rotate. For IT teams, this means an ongoing flood of password-related support tickets; for users, it means friction and weariness. Worse, passwords provide no context on who is using the system and under what conditions; an attacker using stolen credentials seems to be a legitimate employee on the network.

Passwordless authentication shifts the equation. Single sign-on (SSO), biometrics, and digital certificates reduce the need for shared secrets, resulting in a more secure and smoother user experience. Certificates, in particular, present a crucial context for identity. They can validate not just the user’s identity, but also what kind of device they’re using, whether managed or unmanaged, their compliance status, and the user’s role in the organization. This broader identity fabric makes it significantly more difficult for attackers to spoof legitimate users.

Several organizations have been testing FIDO2-based authenticators like Windows Hello or Apple Passkeys, but they lack policy flexibility and device-level context for scalability. On the other hand, certificates can be centrally maintained, integrated with MDM and IdPs, and extended across users and devices. Many organizations utilize FIDO2 for user convenience and certificates for enterprise identification and Zero Trust enforcement.

Certificates and PKI provide a foundation of Zero Trust Network Access (ZTNA) in a Zero Trust framework. They enable continuous trust validation and fine-grained segmentation, ensuring that access decisions are adaptive and risk-aware, rather than one-time checks.

The Biggest Hurdles of Going Passwordless

Despite the apparent benefits, many businesses hesitate to use passwordless authentication completely.  On paper, it promises improved security, a better user experience, and fewer IT tickets, but the route to adoption comes with challenges.  IT and security experts frequently identify the following challenges as ones that might impede, or even derail, a transition.

Legacy Dependencies

Active Directory is still widely used in business contexts. Approximately 90% of enterprises still use Active Directory for identity and access management, while 40% of hybrid organizations utilize on-premises AD as their primary security store. Many outdated apps and devices may not support certificate-based authentication, making the transition expensive and risky.

User Acceptance and Resistance

Employees are wired to use passwords because that’s what they know. Even basic alternatives might seem odd. Shifting established habits frequently results in confusion, increased helpdesk demand, and adoption resistance. Well-intentioned initiatives that lack clear training and communication might result in frustration rather than progress.

Device Onboarding at Scale

Rolling out certificates to thousands of endpoints, corporate laptops, mobile devices, IoT sensors, and BYOD hardware can rapidly become a logistical headache. Manual enrollment, even with native tools such as Microsoft’s AD CS or SCEP, is vulnerable to human errors and misconfiguration.

Without automation, IT teams struggle to:

• Determine which devices have valid certificates.
• Ensure that renewal is completed before the expiration date.
• Revoke compromised or deactivated certificates without delay.

To overcome these issues, the industry is moving toward the ACME protocol, which is now widely accepted as the modern standard for automatic certificate enrollment. Apple, for example, requires ACME to support Managed Device Attestation on their platforms.

Recover and Failover

Passwords have one significant advantage: they are recoverable. Forgot yours? Reset it. That fallback does not exist in passwordless situations. If a private key is lost with a stolen device, or a biometric fails, companies must provide backup recovery paths that do not reintroduce weak links.

Here are some common approaches:

• Magic links or one-time recovery codes are provided to a verified channel.
• Fallback authentication methods include hardware-backed tokens (such as YubiKeys and FIDO2 keys).
• Device certifications are reissued by the helpdesk using controlled workflows.

The key challenge is balancing business continuity with zero-trust principles. Recovery solutions must be phishing-resistant; otherwise, shortcuts such as magic links or OTPs risk returning the same vulnerabilities that passwordless was designed to avoid.

Operational Complexity

Every certificate-based deployment has a complex infrastructure stack:

• PKI will issue and validate certificates.
• RADIUS and EAP-TLS are used to enforce authentication for network access.
• Identity Providers (IdPs) such as Azure AD or Okta can give user context.
• MDM platforms for distributing and managing certificates on endpoints.

Every system has its own lifespan and integration specifics. For example, a certificate expiring in the CA does not always sync perfectly with the IdP’s revocation logic, resulting in orphaned credentials that seem “valid.”

This is why certificate lifecycle management tools (CLM tools) have become the standard practice. They give visibility into all of these moving pieces, require renewal before expiration, and coordinate revocation events across systems. Without insight into the certificate lifecycle, IT teams risk disruptions (e.g., expired certificates preventing Wi-Fi access) or compliance breaches (e.g., failure to revoke compromised keys). Gartner has continuously identified certificate lifecycle management as a significant vulnerability in enterprise IT operations, particularly given the increasing number of short-lived certificates.

Beyond these common issues, four deeper operational challenges appear:

Team Silos and Unclear Ownership

PKI deployment involves the security, identity, network, and endpoint teams. When people don’t know their responsibilities, everyday problems like an expired certificate or an authentication outage may escalate into blame games. A network team blames security, but security points to endpoints. Nobody owns remediation.

Lack of Scaling For Automation

Passwordless pilots operate smoothly on a small scale. Without full automation, administrators get caught in manual certificate issuance, revocation, and policy updates. Instead of a straightforward implementation, passwordless becomes an operational burden rather than a strategic advantage.

Modern automation tools mitigate some of these issues by connecting directly with platforms like Intune, Jamf, and Workspace ONE. These integrations automate certificate issue, renewal, and revocation, ensuring that devices remain compliant without frequent administrator interventions. Organizations that skip this automation layer risk overloading IT workers and reducing the long-term value of passwordless efforts.

Best Practices: How To Go Passwordless Seamlessly

Successful organizations consider passwordless a well-executed strategy based on automation, visibility, and adaptive security. The recommended practices below can help set you up for a successful transition.

Automate the Device Onboarding

Manual certificate deployment is one of the most common reasons PKI implementations fail. SecureW2’s JoinNow eliminates this effort by automating certificate enrollment across all device types – managed, unmanaged, BYOD, and IoT.  Instead of relying on your IT team to manually push profiles, enrollment procedures link with MDMs and provide users with guided self-service portals.

Adopt Certificate-Driven Cloud RADIUS

Traditional credential-based RADIUS servers authenticate users and passwords but provide no information about the connected device.  A certificate-driven Cloud RADIUS works differently: it authenticates the device by verifying a single, non-exportable certificate stored in its secure enclave or keychain. Because the certificate cannot be duplicated, disseminated, or phished, stolen credentials provide no value to attackers, and only enrolled, trusted devices obtain network access.

EAP-TLS, the protocol which drives certificate-based RADIUS, reduces the risks of credential replay and phishing. Unlike passwords or tokens, which may be intercepted and reused, each TLS session requires a distinct cryptographic handshake that is linked to the device’s private key. Because the private key never leaves the secure enclave, attackers are unable to capture or replay it, thereby eliminating one of the most prevalent attack routes in credential authentication.

Enable Adaptive Policies

Static access controls don’t align with Zero Trust principles. A certificate-driven Cloud RADIUS connected with an organization’s IdP and MDM enables the enforcement of adaptive rules.  Access might be limited based on device posture, role, time of day, location, or compliance status.  For example, a business laptop with the most recent security updates may obtain full access, but a personal tablet is limited to a guest VLAN.  This contextual, continual trust evaluation mirrors Zero Trust principles and is consistent with the “assume breach” concept promoted by leaders such as Lisa Porter in her DoD talk.

Plan for Hybrid and Legacy Environments

Passwordless adoption does not occur in a vacuum.  Most businesses support older software, IoT devices, and partner systems that do not require certificates.  In this case, backup techniques such as SAML portals, MAC-based authentication, and guest access flows offer coverage.  SecureW2 enables a hybrid architecture in which certificate-based authentication coexists with transitional flows, providing business continuity while maintaining security.

Prioritize Visibility and Management

When organizations adopt PKI to go passwordless, visibility becomes just as important as authentication. A single certificate lifecycle management, logging, and analytics platform fills this void.  Industry-standard certificate lifecycle management (CLM) platforms such as Venafi, Keyfactor, and AppViewX, as well as SecureW2, address this need by centralizing certificate issuance, renewal, revocation, and monitoring. Clear dashboards and SIEM integrations allow IT and security professionals to identify which people, devices, and apps are connecting, as well as whether they comply with policies.  This visibility is critical for compliance audits and speedy incident response.

Adopt a Fully Managed Approach

Finally, corporate IT employees should not bear the full burden of managing PKI and RADIUS.  Organizations can cut operational expenses while gaining resilience and scale by outsourcing these components to a cloud-native provider with a worldwide presence and SLAs of 99.999%.  This “PKI-as-a-service” paradigm matches the industry’s overall automation and shared accountability trend.

Conclusion

Passwordless is no longer a distant vision; it’s a transformative step forward in how organizations protect identities and devices.  While challenges like legacy systems, user adoption, and operational complexity persist, the correct approach makes the transition possible.  Organizations may create a phishing-resistant basis for Zero Trust by integrating certificates, Cloud RADIUS, and adaptive policy enforcement without requiring disruptive overhauls.

SecureW2 enables IT leaders to effortlessly upgrade authentication, providing a managed and scalable road to passwordless security.  Contact us to see how your organization can take the next step now.