It appears that once again there are conflicts with Sophos and the most recent (MAY) patch Tuesday from Microsoft.
"Its advice on what to do is pretty blunt: uninstall the Windows update. Specifically, revert KB4499164 (May's full-fat Patch Tuesday) and KB4499165, the security-only update. As regular readers know, the latest Patch Tuesday is intended to mitigate a pretty nasty vuln (CVE-2019-0708) which permits unauthenticated remote code execution through the medium of Remote Desktop Services. Sophos itself opined that it was "so serious that Microsoft has even released patches for its long-unsupported operating systems, Windows 2003 and XP"."
This is critical. Please provide an ETA on resolution and rollout.
Hello Matthew Renner
There is no ETA currently: Please refer to the community post linked below. The KB article in that post will be updated for any changes to the status of the issue.
[Sophos Notification] Following the Microsoft Windows 14th May update some machines hang on boot
We apologize for the inconvenience. At the moment, developers are actively working with Microsoft and the investigation is ongoing.