We are in the process of being divested from a large corporation. To get our business unit up-and-running as quickly as possible after the sale, I setup Office 365 and created accounts for all of our employees. We are currently still operating on the ex-parent company's Active Directory, but in the process of setting up our own Active Directory. My plan is to migrate computers, users and groups (using ADMT) from the ex-parent AD to the newly created AD so that I can keep the SID history to continue to allow access to resources that are coming over to our new AD.

QUESTION: Since I will have accounts in my new domain and accounts in my Office 365 tenant that match; how do I get DirSync to start sync'ing password changes between the On-Prem AD and Azure AD? NOTE: I plan to set the UPN of my On-Prem AD to match the Azure AD UPN.

BTW: Our AD will be running Windows Server 2012 R2. If anyone has information about whether we have DirSync or Windows Essentials to handle the integration and synchronization, it would be very much appreciated.

Thanks, Jason


I would use the new Azure AD Connect tool. you can download the latest version from your O365 portal.

You can find all the information you need about Azure AD Connect here:


And this article shows you how to prepare users before provisioning:


  • Hi Michael, thanks for the links. This looks like the right route to go. Since we already have an existing On-Prem AD (the objects being migrated from the ex-parent) and an existing Azure AD/O365, I will make sure to closely read through the "Match the on-premises UPN with the Office 365 UPN" and also "How to prepare a non-routable domain (such as .local domain) for directory synchronization." as we are using this as well. Once we test this out, I will mark this as the correct answer. Thanks again!
    – JasonBub
    May 9 '16 at 15:05

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