Tag Archives: IdFix

Moving from Exchange 2010 to Office 365

There are a lot of articles on the Internet on how to create a hybrid environment, where Exchange 2016 is connected to Office 365. Now that’s fine, but when you’re running Exchange 2016 you most like are NOT going to move to Office 365 anytime soon I guess. If you are running Exchange 2010 chances are that you will move to Office 365 (soon), but there aren’t that much articles about moving from Exchange 2010 to Office 365. And a lot of the articles available don’t have the right approach I’m afraid, and will result in you (the customer) having to pay way too much money to your system integrator.

In this article, I’ll try to outline the recommended approach when moving from Exchange 2010 to Office 365 in a hybrid scenario. With Azure AD Connect for synchronization purposes. Cliffhanger: I’m not going to install Exchange 2016 into the existing Exchange 2010 environment Smile

Existing Exchange environment

Our organization is called Inframan and they have their own on-premises Exchange 2010 environment which they have been running for 5 years now without too much issues. There are internal Outlook clients using Outlook 2010 and higher, and there are external clients using Outlook Anywhere. There are also mobile clients using ActiveSync to connect to their Mailboxes. Of course, there is Outlook Web Access, but POP3 and IMAP4 are not used.


Figure 1. Overview of the Inframan Exchange 2010 environment.

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Implementing Directory Synchronization

Updated: November 11, 2015,

In an earlier blog I explained the differences between Cloud Identities, Linked Identities and Federated Identities. The source of authority (i.e. where the accounts are managed) for Cloud Identities is Microsoft Online and for Linked and Federated Identities the source of authority is your on-premises Active Directory. To get these accounts in Azure Active Directory (Office 365) you have to setup a directory synchronization between Active Directory and Azure Active Directory.

As explained earlier I prefer to use a dedicated DirSync server instead of installing DirSync on your Domain Controller (which is possible and supported). When using a dedicated DirSync server, you can keep your Domain Controllers identical and work on your Domain Controllers while not affecting your DirSync server. We now will build a configuration like this:

Implemented DirSYnc server

There are two options when setting up Directory Synchronization between your on-premises Active Directory and Windows Azure Active Directory:

  • DirSync as a tool that can be downloaded from the Microsoft Online Portal. This is the ‘original’ DirSync tool which can be installed on a Domain Controller or on a dedicated DirSync server. This tool will be decommissioned somewhere in the (near) future.
  • Microsoft Azure Active Directory (WAAD) Sync Services, the new DirSync tool that can be downloaded from http://www.microsoft.com/en-us/download/details.aspx?id=44225. This tool has the option to synchronize a multi-forest topology with one tenant in Office 365.

Note. On June 24, 2015 Microsoft has released the Azure AD Connect & Connect Health. Azure AD Connect is the latest version of the Directory Synchronization. This blog is based on the previous Azure AD Sync, but I strongly recommend you look into the Azure AD Connect tool (there are a lot of similarities) which you can download from the Download center.

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