Hey everyone, I could really use some advice about migrating away from an old on-premises setup. My company is still using Windows Server 2008 for our primary functions—File, Print, Domain Controller, and DHCP along with an ERP server. We're planning to move towards a more cloud-centric model, especially since we'll be adding laptops to improve mobility before the October end of support for these old systems.
Currently, our domain is oldcompany.com and we've got the backup Domain Controller and some computers running on outdated hardware. We've already migrated our email to Microsoft 365 Business Standard, but I'm now considering how to effectively connect our local network to the Microsoft 365 environment.
Here are my main questions:
1. Can we connect our existing local domain (forest) to our Microsoft 365 forest?
2. Is it possible to join devices directly to the Microsoft 365 domain, and will it handle the login authentication?
3. If we set up a temporary Windows Server 2016 for Entra Connect, what sign-in method should we choose? I'm considering Password Hash Synchronization among others.
Any additional thoughts or concerns about my proposed setup would also be appreciated! Just a heads up, I've inherited this system and have no budget for major upgrades except for the Firewall/Gateway and replacing some dying drives. Our team has shrunk from over 30 employees to just eight.
1 Answer
I’d suggest joining the laptops directly to Entra and upgrading to Business Premium for the added features like Intune and Defender. When it comes to hybrid AD, unless you’re confident in managing it, my advice is to skip it and go fully cloud-based instead.
That’s the plan! But I imagine the boss will still want some sort of physical backup on-prem.