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do I need to deactivate directory synchronization for cutover migration

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 I have read one article "migrate all mailboxes to the cloud with a cutover exchange migration" that says "If you’ve activated and installed the Microsoft Online Services Directory Synchronization tool, you can’t run a cutover Exchange Migration. If you’ve installed the directory synchronization tool, you can deactivate directory synchronization and then run a cutover Exchange migration. For more information, see Manage directory synchronization." However, If I follow those links out to "Directory Synchronization and Source of Authority" there's a section where it says "Enabling AD FS 2.0/SSO requires directory synchronization. However, the previous version of the Directory Synchronization tool could not be run after some of the Exchange migration tools had already been run. Specifically, a cutover Exchange migration migrates users and mailboxes to the cloud by first creating a user account that is based on the SMTP address.

The previous version of directory synchronization did not create new cloud users if an existing user object in the cloud had the same primary SMTP address as the corresponding on-premises user. However, the current version of directory synchronization uses SMTP match functionality (described earlier in this article) to match on-premises users to cloud users."

I am doing a cutover migration and I want to use ADFS and SSO (in fact ADFS and SSO are already set up for two of my 5 active domains) 

Do I turn it off, migrate mailboxes, then turn it back on, or can I just leave it on?

All Replies
  • What are you migrating from, Exchange? The intent with Directory Sync and ADFS, with Exchange in the mix is that you use a Exchange 2010 Hybrid Server to move the mailboxes to Office 365.

  • I'm migrating from Exchange 2003

  • The best option would be to use an Exchange 2010 Hybrid Server and move the mailboxes to Office 365.

    You can plan the migration using the Exchange Deployment Assistant.

  • Thanks I'm reading that. ON a related note, regarding Outlook email profiles, most of what I've read says that those have to be manually re-created after a migration. However, I read one post that said Outlook 2010 would recognize the migration and update automatically. All our users have Outlook 2010. Is there a way to simplify profile migration?

  • Yes, Outlook 2010 will pickup the changes and update the profiles automatically if you move the mailboxes with the Hybrid Server in place.

  • Excellent, my plan is to convert to a fully cloud based solution- does the link you sent me (haven't made it all the way through yet) get to the stage of decommissioning on premises Exchange?

  • Yes, at the end, you swap the MX record to Office 365 and decommission Exchange on-prem.

    If you have questions fire me an email.

  • Hi KelseyE,

    Thank you for your information.

    Hi Joe,

    Does KeylseyE’s answer solve the issue?

    Please note in order to perform a cutover Exchange migration and Single Sign-On, you need to follow the steps below:
    1. Perform a cutover Exchange migration
    2. Convert on-premises mailboxes to mail-enabled users
    3. Implement AD FS 2.0 to enable single sign-on
    4. Activate and install the Directory Synchronization tool
    5. Decommission on-premises Exchange servers (optional)

    For more information please refer to Cutover Exchange Migration and Single Sign-On.

    If you have any questions regarding to the issue, please feel free to post here.

    Kent Gu

  • thanks, I think this gests me almost to where I need to be. The only question I have left is what are the advantages of performing a hybrid migration over a cutover?

  • The Hybrid server will allow you to move the mailboxes and data, along with no outage to the clients. Cut over assumes that you are taking a weekend outage to mail, mail enabled all the cloud accounts, flip the MX record to Office 365 and then move or import all the data back.

    The hybrid method is the better way to do it. With the better way, there are costs. You need another server in the mix (Exchange 2010). The good thing is that you dont need to purchase a license for this. Email Microsoft support through the MOP and they will provide the key. You will also need a public certificate for the Exchange server.

    Email me if you have anymore questions.

  • Hi Joe,

    There are few different migration methods you can choose according to the situation. Below is a brief information among them:
    - Move requests with the Mailbox Replication Service (MRS)
    The Microsoft Exchange Mailbox Replication Service (MRS), which resides on all Exchange 2010 Client Access servers, is the service responsible for mailbox moves, importing and exporting .pst files, and restoring disabled and soft-deleted mailboxes.

    If you plan to migrate and implement a long-term hybrid deployment with Exchange on-premises, move requests are the recommended way to migrate mailboxes.
    Also, for large organizations that are running Exchange 2003 or Exchange 2007 on-premises and plan to move all mailboxes to the cloud over a period of several months, using move requests as a tool for a long, staged Exchange migration, which is essentially a hybrid deployment, may make sense.

    - Cutover Exchange migration
    Cutover Exchange migration is for organizations that have fewer than 1,000 mailboxes and want to move all mailboxes to the cloud in a single operation. Use E-Mail Migration in the Exchange Control Panel to access the tool.

    - Staged Exchange migration
    Staged Exchange migration is for larger organizations or organizations that want to migrate mailboxes to the cloud over time. In this scenario, you can migrate some mailboxes to the cloud while maintaining the rest of the mailboxes in your on-premises organization. Use E-Mail Migration in the Exchange Control Panel to access the tool.

    - IMAP e-mail migration
    IMAP e-mail migration is designed as a fallback e-mail content migration tool for a wide variety of e-mail servers. If you are running Exchange 2000 Server or Exchange Server 5.5 Service Pack 4, or any other compliant IMAP server, such as Gmail, IMAP e-mail migration is an option. Use E-mail Migration in the Exchange Control Panel and a CSV file.

    - PST Capture
    Another method for migrating mailbox items to cloud mailboxes is Microsoft Exchange PST Capture. PST Capture lets you search for and collect PST files on computers in your on-premises organization and then import the PST files to cloud mailboxes. Note that you can also use PST Capture to import PST files to on-premises primary or archive mailboxes.

    The picture below may help you to get a better idea among these methods.

    For more information please refer to Exchange Hybrid Deployment and Migration with Office 365.

    Kent Gu

  • Hi Joe,
    How are things going?
    If you have any other questions or concerns, please do not hesitate to contact us. It is always our pleasure to be of assistance.
    Kent Gu