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docker info only proves the daemon answers, so the Windows CI passes the check and then dies trying to run a linux image. The hosted Windows runners cannot run one: GitHub states the VMs are not enabled for nested virtualization and will not be, since they already sit one level deep and the hypervisor does not support more levels (https://github.com/orgs/community/discussions/25491). Probing the image itself skips those tests there, and pulls it before the server waits for the container id.