Platform Single Sign-On enhances macOS device identity with Microsoft Entra ID for more secure authentication. However, simply registering for Platform SSO does not guarantee a passwordless experience. Enabling the Company Portal AutoFill extension is crucial for passwordless sign-in in Safari, Microsoft Edge, and Google Chrome. In many deployments, this requires manual user intervention, leading to inconsistent results. This article proposes automating the enabling of Company Portal AutoFill after Platform SSO registration to eliminate user dependency. The process requires both Platform SSO registration and Company Portal AutoFill to be active for passwordless authentication. When Platform SSO registers after Setup Assistant, users are prompted to enable AutoFill, but this remains a manual step they can overlook. Automating this step is particularly beneficial when combined with the "Enable Registration During Setup" setting. A custom script, Check-PSSO.zsh, can detect completed Platform SSO registration and automatically enable AutoFill. This script waits for a user session, verifies Platform SSO, detects the AutoFill extension, and then enables it programmatically. The script supports Safari, Microsoft Edge, and Google Chrome. It requires macOS 15 or later and Company Portal version 5.2604.0 or later. Deployment is recommended via Intune using a PKG with a pre-install script. Automating AutoFill improves deployment consistency, security, and zero-touch provisioning.