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SBS 2008/2011: Migrating Email to Office 365

As Windows Small Business Server (SBS) 2008 will become somewhat obsolete in 2017 due to Exchange Server 2007 falling out of support, and given that SBS 2011 is no longer available for new systems, a common migration plan for the email system is to use Office 365. This enables the on-premises server to remain in use, providing file, print, networking and Active Directory services, but for the Internet-facing services such as inbound SMTP, Outlook Web Access and Outlook Anywhere to be turned off.

One process for this migration is as follows:

Planning

  1. Catalog the users, aliases and public folders in use. Are there any mailboxes that can be deprecated or merged?

  2. Consider the total size of the email store and how long this data will take to upload through your connection.

  3. Consider how many other Internet services you can use temporarily to upload mailbox data into the Office 365 tenancy (eg user's home connections).

  4. Consider the best time for the migration — does the business have a quiet time?

  5. Consider how you'll operate your domain's DNS records. See also External Domain Name System records for Office 365.

  6. Check your client software is supported. For example, Outlook 2003 and, as of late 2017, Outlook 2007 will not connect to an Office 365 mailbox.

Preparation

  1. If using ADSL, switch your service to use Annex M to increase upload speed where possible; if using NBN, switch to the highest possible speed plan. As these speed changes often only take effect at plan rollover dates, organise them in advance to match the migration window.

  2. Create your Office 365 tenancy, and configure the mailboxes, shared folders, aliases and so on. At this point you can add your domain(s) to the tenancy but you can leave the DNS settings as they are (probably on a third-party DNS provider).

  3. Ensure the mailbox message size limits exceed those of the on-premises limits. Or simply set the message limit to 153600 (153,600Kb = 150Mb). The default limit is 35Mb.

  4. Use the Office 365 Client Performance Analyzer to check for connectivity issues, and tune your network ahead of time.

  5. Ensure the server backup is working, and add another backup drive to the rotation.

Migration

  1. The day before the migration, set the domain's MX and Autodiscover records to a shorter timeout, say 300 seconds.

  2. The night before the migration, update the DNS records appropriately, either by moving the domain into the Office 365 tenancy or updating the records on the third-party provider. From this point, inbound email will start to flow to the Office 365 mailboxes, but the change may take up to several hours, despite using a shorter DNS timeout, particularly if you redelegated, so it is best to leave the on-premises system operational overnight to receive any messages that arrive before the senders' DNS has updated the MX.

  3. The next morning, SMTP, Outlook Web Access and Outlook Anywhere services can be blocked (usually ports 25, 443 on the router).

  4. Last night's server backup should be archived; never to be overwritten.

  5. For each user, log in and open Outlook. Let it sync all folders, then export the mailbox to a personal folders file (PST). Take note of other settings such as Safe Senders. Then log out.

    (Another way to archive mailboxes to PST is Exporting Mailboxes to Personal Folders Files for SBS 2008 or Exporting Mailboxes to Personal Folders Files for SBS 2011.)

  6. Update the login script with the following commands:

    reg add HKCU\Software\Microsoft\Office\12.0\Outlook\AutoDiscover /v ExcludeScpLookup /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\14.0\Outlook\AutoDiscover /v ExcludeScpLookup /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\15.0\Outlook\AutoDiscover /v ExcludeScpLookup /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\16.0\Outlook\AutoDiscover /v ExcludeScpLookup /d 1 /t REG_DWORD /f

    reg add HKCU\Software\Microsoft\Office\12.0\Outlook\AutoDiscover /v ExcludeHttpsRootDomain /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\14.0\Outlook\AutoDiscover /v ExcludeHttpsRootDomain /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\15.0\Outlook\AutoDiscover /v ExcludeHttpsRootDomain /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\16.0\Outlook\AutoDiscover /v ExcludeHttpsRootDomain /d 1 /t REG_DWORD /f

    reg add HKCU\Software\Microsoft\Office\12.0\Outlook\AutoDiscover /v ExcludeSrvRecord /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\14.0\Outlook\AutoDiscover /v ExcludeSrvRecord /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\15.0\Outlook\AutoDiscover /v ExcludeSrvRecord /d 1 /t REG_DWORD /f
    reg add HKCU\Software\Microsoft\Office\16.0\Outlook\AutoDiscover /v ExcludeSrvRecord /d 1 /t REG_DWORD /f

    reg delete HKCU\Software\Microsoft\Office\12.0\Outlook\AutoDiscover /v ExcludeHttpRedirect /f
    reg delete HKCU\Software\Microsoft\Office\14.0\Outlook\AutoDiscover /v ExcludeHttpRedirect /f
    reg delete HKCU\Software\Microsoft\Office\15.0\Outlook\AutoDiscover /v ExcludeHttpRedirect /f
    reg delete HKCU\Software\Microsoft\Office\16.0\Outlook\AutoDiscover /v ExcludeHttpRedirect /f

    reg delete HKCU\Software\Microsoft\Office\12.0\Outlook\AutoDiscover /v ExcludeHttpsAutoDiscoverDomain /f
    reg delete HKCU\Software\Microsoft\Office\14.0\Outlook\AutoDiscover /v ExcludeHttpsAutoDiscoverDomain /f
    reg delete HKCU\Software\Microsoft\Office\15.0\Outlook\AutoDiscover /v ExcludeHttpsAutoDiscoverDomain /f
    reg delete HKCU\Software\Microsoft\Office\16.0\Outlook\AutoDiscover /v ExcludeHttpsAutoDiscoverDomain /f

    ExcludeScpLookup” is the most important option to enable; it causes Outlook to ignore the Autodiscover records that Exchange has added to the domain's Active Directory — this is how Outlook normally self-discovers the appropriate mailbox(es) to open. The other entries also configure various Autodiscovery methods which are not relevant for Office 365 and can confuse Outlook. Additonally, ExcludeHttpsAutoDiscoverDomain should be explicitly disabled in case it has been enabled previously.

    Note that Outlook 2007 clients do not seem to honour these settings properly so it may be necessary to configure the client manually.

    [The Service Connection Point (SCP) record can also be modified via Active Directory using the Active Directory Sites and Services applet (run as Administrator, then use ViewShow Services Node). Navigate to ServicesMicrosoft Exchange<Domain>Administrative GroupsExchange Administrative Group<Server>ProtocolsAutodiscover. Then right-click the server name, choose Properties, and you can see the various details. However this is not recommended. Disabling the SCP Lookup via the registry causes Outlook to behave the appropriate way and can be easily reversed if necessary.]

  7. On the server, open an elevated command prompt and shut down Exchange with the following commands:

    net stop MSExchangeADTopology /y
    net stop MSExchangeIS /y
    net stop MSExchangeSearch /y

    (Note, these services will restart if the server is rebooted. At this point we just want Exchange turned off, not necessarily disabled or removed.)

  8. Log in as each user, and open Outlook. It should use Autodiscovery to find the Office 365 mailbox and prompt for credentials. (Older Outlook clients may need some manual configuration.)

  9. Import the PST and allow the sync to complete.

    If importing other PST files, run a repair on them first.

Post-Migration

  1. Once the migration is complete (email data is fully uploaded and clients have synced fully), the various Exchange services on the server can left as they are, or turned off (set to Manual startup). Leaving Exchange running will not interfere with the clients as the various DNS entries they use will point to the Office 365 service, and Outlook will not query the local servers for mailboxes since ExcludeScpLookup is turned on. However, disabling Exchange allows the server to recover memory and CPU resources. Note also that is Exchange is switched off, the default SBS wizards will not work properly, such as creating users, as they expect to be able to manipulate the email system.

    If you feel Exchange is best switched off in your environment, this can be done via an elevated command prompt with the following commands:

    SBS 2011/Exchange Server 2010

    sc config MSExchangeADTopology start= demand
    sc config MSExchangeAB start= demand
    sc config MSExchangeAntispamUpdate start= demand
    sc config MSExchangeEdgeSync start= demand
    sc config MSExchangeFDS start= demand
    sc config MSExchangeFBA start= demand
    sc config MSExchangeIS start= demand
    sc config MSExchangeMailSubmission start= demand
    sc config MSExchangeMailboxAssistants start= demand
    sc config MSExchangeMailboxReplication start= demand
    sc config MSExchangeProtectedServiceHost start= demand
    sc config MSExchangeRepl start= demand
    sc config MSExchangeRPC start= demand
    sc config MSExchangeSearch start= demand
    sc config MSExchangeServiceHost start= demand
    sc config MSExchangeSA start= demand
    sc config MSExchangeThrottling start= demand
    sc config MSExchangeTransport start= demand
    sc config MSExchangeTransportLogSearch start= demand

    SBS 2008/Exchange Server 2007

    sc config MSExchangeADTopology start= demand
    sc config MSExchangeAntispamUpdate start= demand
    sc config MSExchangeFDS start= demand
    sc config MSExchangeIS start= demand
    sc config MSExchangeMailSubmission start= demand
    sc config MSExchangeMailboxAssistants start= demand
    sc config MSExchangeRepl start= demand
    sc config MSExchangeSearch start= demand
    sc config MSExchangeServiceHost start= demand
    sc config MSExchangeSA start= demand
    sc config MSExchangeTransport start= demand
    sc config MSExchangeTransportLogSearch start= demand

  2. Later, when you're sure you won't need to refer to the old system, consider whether it is appropriate to uninstall Exchange Server completely. Note that this process is very drastic so you would need to assess that the positives of removing Exchange (reclaiming resources) outweighs the negatives (breaking standard SBS components).

  3. If there is a need to refer to the old database, restore the pre-migration backup into a virtual machine or some other hardware.

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