How are you pushing software to remote users who rarely VPN in?

Posted by m0zi-@reddit | sysadmin | View on Reddit | 59 comments

We’ve got domain-joined Windows machines out in the field. Our VPN is user-initiated after Windows login, so there’s no always-on tunnel. Users only connect when they need to, which means GPO and anything that depends on line-of-sight to a DC is unreliable for software deployments.

Right now we have ConnectWise RMM and ScreenConnect, so I can remote in and install things manually, but that obviously doesn’t scale.

Appreciate any insight. Ideally looking for something that doesn’t require a massive lift to implement since we’re pretty spread thin as it is.

Thanks.