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Recreating Remote Desktop Services Email Profiles During Office 365 Migration

Timothy Longueil

Jun 13 2019

2 min read

One challenge I encounter more frequently when I perform an email migration is having to recreate users’ Outlook profile in a Remote Desktop Service (RDS) environment. Recently, I was tasked with an Office 365 migration for over 150 users, where an RDS environment was in use for email and collaboration. This environment included Windows Server 2012 R2, Microsoft Office 2016, and an Active Directory Domain.

Overview:

Create registry key for Outlook profile to install on user login; registry file placed in NETLOGON share.
Remove SCP Autodiscover service entry for local on-premises Exchange within Active Directory.
Update DNS Autodiscover entries to point to Office 365 via CNAME.
Create Group Policy Object with new organizational unit and move RDS servers there.

The steps to accomplish this task are explained in detail below:

Start with creating a .reg file in notepad that contains the follow registry keys associated with the Outlook profile. Note the section in red, this is the expected Outlook “profile name.”reg add HKCUSoftwareMicrosoftOffice16.0OutlookProfilesOffice365
reg add HKCUSoftwareMicrosoftOffice16.0Outlook /v DefaultProfile /t REG_SZ /d “Office365” /F
Next, log into Active Directory Sites and Services, navigate to the Services node, and remove the SCP entry for the Exchange Autodiscover record. See below for path to find the service.CN=Autodiscover,CN=Protocols,CN=ServerName,CN=Servers,CN=Exchange Administrative Group,CN=Administrative Groups,CN=First Organization,CN=Microsoft Exchange,CN=Services
DNS management is next — verify that the internal Autodiscover A and SRV records are removed, and create a CNAME record to point to Offce365 at autodiscover.outlook.com.
Finally, create a new GPO with the following settings and apply this to the RDS organizational unit inside Active Directory that contains the RDS servers. Reboot the RDS servers to apply the policies.
Now, the next time a user logs into an RDS server, they get presented with a new profile window when launching Outlook. All they need to do is click Next and the profile is configured to connect to Office 365.

This was highly successful and made for an extremely smooth migration for all parties involved.

Do you have a Remote Desktop Services environment in which you’ve been struggling, or have a lack of confidence to move to Office 365 because of the amount of manual effort needed? Contact the Sikich team to start your migration to Office 365 today and rest easy tomorrow!

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About the Author

Timothy Longueil

Timothy Longueil is a Senior Network Consultant and Project Engineer at Sikich that works closely with organizations to improve productivity and increase overall profit. Timothy also holds many advanced certifications, including Microsoft 365 Enterprise Administrator Expert (M365 EA), CompTIA A+, CompTIA Network+, Certified SonicWALL Security Administrator (CSSA) Microsoft Certified Solutions Expert (MCSE) and Microsoft Certified Solutions Associate (MCSA). Timothy’s attention to detail allows him to troubleshoot as well as to design and deploy advanced, complex solutions for organizations in the Chicagoland area while providing documentation, communication, support, and sales alongside working closely with the key decision-makers of the organization. Timothy has performed 50+ Microsoft 365 Exchange Online migrations and Teams Phone System deployments for clients, and is currently performing new deployments in the rapidly emerging Microsoft Cloud Technologies Platform. Timothy’s primary areas of focus are Microsoft cloud services such as Azure or Microsoft 365, Windows Server and Active Directory, Virtualization through either VMware or Hyper-V, Backup/Disaster Recovery/Business Continuity and Network routing/switching/security/VPN.