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I'm just looking for some guidance here. Maybe a, "Hey, check out this link/book/video that shows how to get started with Azure" Everything I've found on the web is either too specific or too general to be of much help.

We currently have a local AD domain and an Office 365 subscription for email. They both have separate user/resource accounts. Our local network is contoso.local and our O365 is contoso.com. We have a local dns with 2 zones, contoso.local and contoso.com (don't ask me why, I just took over and no one knows the reasoning behind it). We have around 450 AD objects in our directory. I'd like to get to a point where users have a SSO to access both local and O365 resources.

I also have a business critical VM that provides EDI services for our company. Before I arrived here, it had a history of going down a lot, causing hundreds of thousands of dollars worth of lost/missed sales and shipments. I'd like to move that to Azure for maximum availability.

I know, this reads like a certification question. But here's what I've considered so far:

  1. Install Azure AD Connect and synchronize our local AD to Azure. I actually started down this road until I began asking myself how this would fix my SSO problem. Would this solution synchronize my .local accounts to my .com directory? Or, would it simply create a new .local database in Azure? I simply don't know.
  2. Migrate our existing contoso.local domain to a new contoso.com domain then synchronize with Azure. Again, I started down this road until I realized that I would have conflicting NETBIOS names. Scratch that plan.
  3. Azure AD DS? AD Federation Services? Ok, I'm just not versed enough in how Azure and Windows can integrate. I'm grasping at straws now.

Help me Obi-Wan Kenobi...you're my only hope!

DLorien
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  • I would expect any proper solution is going to begin with renaming your domain and dealing with whatever problems might arise. You don't have on-premise Exchange so it really shouldn't be that bad... – Michael Hampton Sep 07 '18 at 20:52
  • In this situation I would first ask whether the local AD is necessary or not. Synchronizing with Azure AD Connect would cause duplicate accounts, the question being "how could I merge these with the cloud accounts". However, if there's no service depending on the local AD, it might be easier to move the workstations to Azure AD and migrate the local profiles to Azure AD profiles. That would be the easiest way to get rid of `contoso.local`, although it doesn't prevent using Azure AD Connect: the equivalent for this domain on Azure side would be the `contoso.onmicrosoft.com`. – Esa Jokinen Sep 08 '18 at 05:08

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