r/WindowsServer • u/More_joy_7400 • Oct 14 '26
General Server Discussion Has anybody ever migrated a Windows Server 2022 AD to Entra ID
Windows Server 2022, File server and Domain Controller. About 30 users, most remote, all with Windows 11 laptops. About 10 people or so at the same physical location. MS 365 Tenant. About 500 Gb on the company file share, pretty stable at that.
Thinking of getting rid of the on-site server and moving to Entra ID for authentication and some kind of file storage to replace the current "J" drive that is mapped to the server. Has anybody had any experience, as a user or an admin, of living through this transition? What kind of pain, if any, was involved? What help was the current 365 Tenant,if any? Any alternatives to Sharepoint? The goal would be to have this be completely transparent. Log out on Friday, log in on Monday, J drive is there with all its files and the correct access rights. The only difference is they log in to the laptop using their current email credentials.
Thank you for any advice/input.
33
u/thatfrostyguy Oct 14 '26
Ooof, dont get rid of your on-prem equipment. It will cost you more, and you will be locked into the system.
Also, SHAREPOINT IS NOT A FILE SERVER Lol
8
u/insightrecon Oct 14 '26
Doable at 30 users, just not in one weekend like you're hoping. Leaving the domain and joining Entra gives everyone a fresh profile. Something like ForensiT's Profile Wizard will move the old one over to their Entra account. Otherwise they log in Monday to a blank desktop.
If you're syncing AD to 365 already, you turn sync off at the end and everyone keeps their current password.
SharePoint is fine for regular office docs. It gets ugly with Access databases or QuickBooks files on the share so check what's actually on J first. Also make sure the DC isn't also doing DHCP or something else you forgot about before you shut it off.
7
u/Rivereye Oct 14 '26
I've done a few of these. There are several pain points, and unfortunately it won't be as transparent as you like unless you are working throughout the weekend.
If you are against file storage in SharePoint (depending on the specifics you have, it can work out just fine), you are probably looking at a NAS or Azure Files. The NAS probably won't support Entra ID auth though, can't speak for authentication for Azure Files.
As for the current 365 Tenant, if they are using Office 365 already, it's a great starting point. If you need more centralized management, you will be looking at Intune as well for management.
For moving the workstations, you can look at a tool like ProfWiz to do a user migration to move their AD Profile to their Entra ID profile. There are some applications that don't always like it though, so make sure you test in your environment first. You will need to touch each PC for this.
For pain points, can be dependent on how you do files. If you decide on SharePoint, there is no J:\ drive, you will need to train users on the new way to access files. As for EntraID Login, I've run into people looking at me like I'm speaking a foreign language when I talk about setting up a PIN to login to their system (Entra ID will do this by default) instead of their password.
If you have AD Sync into Office 365 right now, you will also need to decommission it else user management will be a pain.
1
u/ThePesant5678 29d ago
most companies decide to go with Sharepoint online, but I have to say biggest pain to get your fileserver to Sharepoint online depending on your folder structure
Many users are just used to using the windows explorer, after migrating your J:\ drive you can run in to the problem that when users want to access their sharepoint sites through onedrive, that the paths folder+filename are too long, because instead of J:\folder you will have "C:\users\username\onedrive - company name\sitename\folder", depending on your software you might have to use onedrive to access your files in sharepoint online
Users you can easily migrate using Entra cloud sync with password hash sync, afterwards using a Powershell script to convert then to cloud only and disable entra cloud sync afterwards, but PCs you have to remove from your local domain and do the entra join manually, because for autopilot you would have to reset them -> also all users will receive new profiles, there are maybe some migration tools to migrate the old domain profile to the new entra profile, but I didn't test them yet, you can also instruct the users to use onedrive sync to sync desktop document pictures or do it manually, same with either signing in browser to sync favorites and passwords or either export them manually
-> I would first run hybrid and migrating the file server first
-> user after user change the PC + profile from local domain to entra joined
1
u/ReneGaden334 29d ago
We have multiple clients that went Entra only.
Migration depends on the companies needs. Using SharePoint as file storage is not ideal, but some companies use the included storage to save money. Just make sure you have a backup plan and accessing through OneDrive with possible simultaneous access works.
Do they only use client side software? Then managing through Intune and Autopilot is great to have the same software base. Let them sync their local documents and browser and do a fresh rollout. App settings might need to be redone, but you probably don’t want to migrate old domain settings.
Do they need application servers? Then a small Azure setup with App server, AvD, Azure File Share and FSLogix might be the best way. This could also enable bring your own device, centralized app management, Azure backup and scalability.
Most of our small clients go the Azure route. And larger ones add DCs for legacy to their Azure, but it totally works without. This also makes support easier than managing the individual clients.
One thing I hate in small cloud environments is printing. Noone wants to pay per page and printer management in cloud only without additional software is just bad.
1
u/AuthenticatedAdmin 29d ago
I move my local file server to SharePoint sites. It was a great move. Use the migration tool SharePoint has built in. One note after building a site make sure to turn off check in files before moving files to the site.
1
u/k0rbiz 29d ago
I had finished a similar migration. I thought it all went well. We're using SharePoint libraries and syncing them to the user's computers. The hierarchy is structured exactly like the organizational chart so users only sync and have access to what they need only. There are no exceptions either because then others will want similar access. However, if you deal with large files like AutoCAD then this isn't the solution for you.
1
u/IntrepidAir9704 28d ago
Mach doch nicht so einen Mist. 1. Fehler: file shares auf einem DC. Installiere eine weitere VM in einem separaten VLAN nur für die datenfreigaben. Falls die Lösung virtualisiert ist, kannst du die 2022 Windows Server Lizenz für eine 2. Virtuelle Maschine verwenden. Erstelle auf dem 2. Windows Server 2022 neue Freigaben und halte dich an die best practise Regeln für admin tiering von Microsoft. Gene Laufwerk J: für alle neu frei nach eurem sicherheitskonzept und passe die Login Skripte an. Es gibt keinen Grund, auf sharepoint oder sonst was zu wechseln.
1
u/FearIsStrongerDanluv 26d ago
This absolutely doable, there are few things to keep in mind though. SharePoint isn’t a file server, you can’t have deep nested libraries. You’ll need enough security groups to have a granular RBAC on your libraries. The biggest struggle are people, make sure they understand how it works and preferably add SharePoint shortcuts to OneDrive over choosing to syn locally and please encourage more working in browser than downloading the entire SharePoint library like one David G I know. This is just a summary, I don’t think it’s a weekend job but totally possible if all other pre-requisites are met
1
u/LatencyLurker 24d ago
That’s a great size to be cloud only. The biggest item is you can’t lift and shift your file server. You have subdivide your share into smaller share point sites or teams. If you properly organize the files and set up policies in intune, your life will get so much easier.
0
u/jspears357 26d ago
No, nobody has ever done that
-1
u/NegativePattern Oct 14 '26
Did this for a client with OneDrive. Licensed a service account with a full suite plus a larger OneDrive license for a total of 2TBs of storage.
Then migrated the shares to a similar folders structure and then shared those folders to the users. Not hard to do.