Need Direction on how to proceed to go Cloud (Azure AD + M365)

Copper Contributor

Hi, I have a customer that is currently using a Windows 2016 Standard server as a DC, with a 2nd server with Exchange 2016 and a 3rd server currently on Windows 2012 with RDS Session Hosts.  They are using Terminal Server sessions for their MS Office 2013 (including Outlook 2013 connected to the Exchange 2016) and they currently have a software that they run on the Terminal server in their sessions that does their production, shipping, accounting.


They want to migrate to cloud everything.  They only have about 15 users.  The accounting/production/shipping software can be run on each computer all pointing to a shared folder on a server (or NAS) instead of running it in the Terminal server sessions.


I wonder what should I do first; how to attack the project.


The goal : 

  • Retire the local DC, the Exchange and the Terminal server. 
  • Repurposing the Win2016 licence to just host a share for the Accounting software and maybe some other local resources or just move to a NAS to host a share.
  • Install the Office 365 on all the Win10 devices (Desktops and Laptops)
  • Install the accounting software to all the devices and point to the Local Share.


Should I do the Azure first? the Office 365 first ?  What Licence should I use for them? they want local Office 365 on devices, not the cloud version. Hosting the mailboxes with Backups and Antispams, anti-malware, anti-virus.  


Any guide out there for a similar project ?


1 Reply

Perhaps the application's vendor has a SaaS version that can ingest existing data?
Otherwise, Office365 migration with optional VDI in Azure and/or Azure File Share for the central application's data.
The level of a license depends on the needs, check the licensing page for detailed info for SMB-level licenses. Optionally you can add additional protection for Office365 data, as well as protect workstations with central reporting and management, etc.
Unless you have anything else, that would allow you to dispose of on-prem AD presence.