Everyone talks about going passwordless. Few discuss what really happens when you try. This session strips away the vendor marketing and delivers hard-won lessons from actual passwordless deployments across enterprise environments. You'll discover why your initial rollout plan will probably fail, which user groups will revolt (and how to win them over), and the surprising technical gotchas that Microsoft's documentation glosses over. Through war stories and real implementation data, we'll walk through Windows Hello for Business deployment, Microsoft Authenticator rollout strategies, FIDO2 security key distribution, and the identity architecture changes that make or break success. You'll leave with a battle-tested roadmap, realistic timelines, and answers to the questions you didn't know to ask—like handling temporary workers, legacy apps, and executives who "forgot their phone."

You will learn:

• Identify the top technical and organizational failure points in passwordless deployments and how to avoid them.
• Match the right passwordless method—Windows Hello, Authenticator, or FIDO2—to each user population in your environment.
• Build a phased rollout roadmap with realistic timelines that accounts for legacy apps, identity architecture, and user resistance.