My initial guess is that the Windows image doesn’t have rsync, which is used by the deployment provider. (And therefore it doesn’t work on Windows as is.) You may try installing rsync yourself to confirm/refute this.
As for deployment in general: it is not a good idea to fire deployments from multiple jobs, unless each job works with disjoint parts, because they can occur simultaneously and interfere with each other. Consider using conditional deployment to restrict deployment to only one job, or using build stages to ensure that only one job is responsible for deployment.