Migrating Email from SBS Exchange to Office 365

In the past few months, I have been working with some clients on moving their existing Small Business Server (SBS) systems over to the Microsoft cloud based Office 365 email system. There are a number of issues and possible gotchas in making this transition which will be discussed here. Note that this blog post is targeted to the small business community with existing SBS 2003, SBS 2008 or SBS 2011 deployments that are looking to move their email services to Office 365, while maintaining their existing network. We will not be considering Office365 migration method in this move as the costs and complexity of implementing this in a small business are prohibitive.

The pre-requisite when performing such a migration, is to plan and work out a migration path for email services. Questions to be considered are:

  1. Do we need to migrate all the old email data, or should some be archived?
  2. Are there old accounts that can be decommissioned?
  3. What distribution groups and contacts need to be migrated across?
  4. Are there any Send As and Send on Behalf of permissions that need to be addressed?
  5. Are there individual permissions on Calendars and Folders that need to be recreated?
  6. How will we move the old email data from Exchange on premises to Office 365?

Moving Email data from On-premises Exchange to Office 365

Central to the entire issue is retaining old emails and settings. There are a number of ways to move the data across to Office365.

  • Export-Import. This method involves exporting the current emails to PST and re-importing them into Office 365 once Outlook has been configured.
  • Migrationwiz.com is a fast and easy way to move mailboxes at a low cost.
  • Office365 Migration wizard. This is a built in tool from Microsoft to help in performing a migration from on-premises Exchange. It requires an Azure subscription and the installation of the Directory Sync tool and has some tough pre-requisites for SMBs. The process is detailed on technet here – http://technet.microsoft.com/en-us/library/jj573653.aspx

One main drawback from using any method that does not synchronize the Office 365 platform to your existing Active Directory is dealing with the issue of Auto-Complete or Suggested Contacts. After the migration, it is quite likely that replies on old emails or emails sent using the stored contact information in Auto-Complete or Suggested Contacts will result in a Undeliverable error as follows:

IMCEAEX-_O=MyDomain_OU=First+20Administrative+20Group_cn=Recipients_cn=bOldLastName@domain.com

#550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found ##

Create Users and Set up Domain in Office 365

In this step, you need to set up and recreate all the users, distribution groups, and domains to match what you have on-premises. In the public DNS, set the MX records to point to your on-premises Exchange until you are ready to receive emails at the Office 365 service. Ensure that the Autodiscover and other DNS services are set up properly.

Setting up the Outlook Profile

One of the main issues with setting up Outlook for Office 365 on an existing SBS domain is the existing autodiscover configuration set up for each user account. The following steps should be followed to ensure a simple, incident free set up of Outlook on Office 365.

  1. Log in to the PC as the user. The configuration is done per user.
  2. Update your PC with a the latest patches, especially Microsoft Office patches and Service Packs.
  3. Log in to the Office 365 portal using the users email address and assigned password.
  4. Install software and connect it to Office 365

  5. You will need to sign in to Office 365 again using the user’s credentials.

  6. The Office 365 setup application will note that manual steps will be required (which involves setting up the Outlook profile as detailed here).

  7. For Office 2007, the registry key is [HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\AutoDiscover]

    For Office 2010, the registry key is [HKEY_CURRENT_USER\Software\Microsoft\Office\14.0\Outlook\AutoDiscover]

    The six entries are all DWORD. (NOTE: all but one entry are set to 1)

    “PreferLocalXML”=dword:00000001

    “ExcludeHttpRedirect”=dword:00000000

    “ExcludeHttpsAutoDiscoverDomain”=dword:00000001

    “ExcludeHttpsRootDomain”=dword:00000001

    “ExcludeScpLookup”=dword:00000001

    “ExcludeSrvRecord”=dword:00000001

    They should be displayed among other entries like this.

  8. Download and run the two AgileIT tools from http://www.agileit.com/news/office-365-autodiscover-xml-tool-released/. Just enter the domain name and click OK.

  9. Now you can Add a new Outlook Profile from Control Panel-Mail (32-bit). You will see the existing Outlook Profile there, which can be kept as a backup, as you may need it later for export to PST purposes.

  10. The local autodiscover settings that have been configured earlier will kick in and set up the account. You will need to log in using the Office 365 credentials.

You can also add the on-premises Exchange profile to this new profile, if you are planning to export the old email data or manually transfer information over to the office 365 account.

With smaller sites, this is a quick and easy way to manage your Office 365 migration. With larger installations, the Office 365 migration wizard using Azure and Directory Sync may be a more efficient method. In the end, it is up to the business owner, with advice from the IT consultant, to work out which method is preferred.

UPDATE: There is a really good article on how to use Azure Active Directory to handle password sync between your local AD and the new Office 365 AD – www.infostream.cc/dirsync-aadsync

11 thoughts on “Migrating Email from SBS Exchange to Office 365”

    1. There are many tools out there that claim to do migrations. I have not tested this one, as it is a paid migration tool. I did try to use the free Outlook AutoConfig, but it did not work.

  1. Thank you very much for sharing this information. Solving the problem was done in an instance.

    Now one more problem to solve before upgrading from SBS2008 to Windows Server 2012 Essentials, moving our existing Sharepoint site to ? ? Skydrive pro but how?

  2. Thanks so much for this info. I’ve been looking for a resolution to this issue for about a year now. These procedures finally fixed this annoying problem.

  3. There’s no documentation about the AgileIT Autodiscover tools, and I’m seeing conflicting information out there. Do you have to run both? This seems unique to each local user profile, is there anyway to set this up once on each PC so any new profile will automatically use the new settings? I’m also seeing posts about from AgileIT about disabling SCP. Is this also required? Hoping for a smooth process and not an “all nighter”.

    1. I have always run both.
      Yes, they are unique to the user profile. I have not had the need to set this up for each PC, as the sites are generally not large.
      I haven’t disabled SCP before.

  4. Really good information, it provides the step by step guide to migrate Exchange 2003 Server to Office 365. I understand that how to migrate Exchange 2003 Public Folders to office 365. I found the good utility named LepideMigrator for Exchange ( http://www.lepide.com/exchangemigrator/ ) that helps to migrate any exchange server to office 365 without any interruption.

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