Because SBS 2008 Standard does not allow integration with Office 365 there is NO password synchronization between your current server and Office 365. If you migrate your SBS 2008 to either Windows Server Essentials 2012 R2 or Windows Server Essentials 2016 this functionality can be restored by running the Office 365 integration wizard. This tutorial assumes that the SBS 2008 is still the one and the ONLY domain controller in your network. If you already have installed another domain controller or you have already moved FSMO roles from your SBS 2008 to a new server (like WSE2012R2 or WSE2016) and/or you have already demoted the SBS 2008 but you still have Exchange Server 2007 installed then this tutorial is NOT for your situation. This document and what comes with it are provided as-is with blunt warning: Use at your own risk, buyer beware. You break your system; you own the resolution as well. We have no liability for what you do, or can't do, or fail to do with this information. Your entire protection is to start over again with a protected backup, or from protected system. If you don't want to accept this idea, please don't use this document. 1. Have Office 365 verify ownership of your domain After signing up for an Office 365 account you need to add your domain and verify ownership. This can be done by creating a TXT file with the value Office 365 gives you. Office 365 will check this value and if it matches this is enough proof that you own the domain. Record type Alias or hostname Value TTL TXT It depends on your DNS host but most of them require you to type @ or leave the field empty MS=msXXXXXX. The value for XXXXXX you will find in DNS records shown when you run the wizard. See screenshots in this tutorial Set 1 hour is most of the time OK Login to your Office 365 account and click Setup –> Domains. Choose Add Domain. Type the domain name you own and click Next In the screenshot, you see you can also choose your DNS host but mine is not listed, I do everything myself because I don’t like anybody else messing around with my DNS records. I need to add a TXT record in DNS with MS=ms12270506 as the value. How that is done on your DNS provider I don’t know, please contact them if you need help on this. After you have added the TXT record click Verify. Remember that this can take awhile depending on the TTL and your DNS provider. Some of those providers require 24 hours for this to propagate, you have to wait. Once the verification process has been completed we can continue. The first option requires you to change name servers to something at Microsoft but I never do that. I choose to manage DNS at my own DNS hosting provider. Click Next. In this step, you will see what the DNS records should look like when migration is completed but we not completed it yet so scroll down. Check ‘Skip’ and click Skip. When the migration is done we will come back here and changed DNS records according to the list Microsoft gives you here. Do NOT change those records now or all will fail. Click Finish Click Finish. It will show ‘Possible service issues’ because we have not yet changed DNS records. Changing DNS records will be done AFTER we have successfully migrated all mailboxes. 2. Check if Outlook Anywhere is properly configured on your SBS 2008 Exchange 2007 Server Normally you should just be fine if you have been using the Exchange Server 2007 on our SBS 2008 as your primary mail server. The Internet Connection wizard (Setup your Internet Address) should have done that for you but there is one ‘gotcha’. Your SBS 2008 must be set up with a trusted certificate. Here is how you check that. From the Windows SBS Console choose Network and then Tab Connectivity. As you can see in my setup I have a ‘Trusted’ certificate and NOT a ‘Self-signed’. If you choose ‘View certificate properties’ you can see that my certificate was issued by Comodo. Now if you do not have a Trusted certificate you need to get one and configure your server that certificate before you continue. Office 365 migration will fail if you don’t have a trusted certificate. 3. Connect Office 365 to your Exchange Server 2007 on the SBS 2008 and migrate your mailboxes Login to your Office 365 account with the Global Administrator account. Most of the time that is the account that was first used to purchase an Office 365 subscription. In this step, we create a Migration Endpoint and set the user who is able to actually migrate Exchange data. In most cases, this is the Domain Admin on your SBS you would normally use the administer the server. Once that is done a new migration batch is created and we will start that automatically. Once migration is completed and DNS is changed to point all DNS records to Office 365 you can remove that batch. Choose Amin centers and then Exchange. Choose Recipients and then ‘migration’. Add a Migration Endpoint Click the + sign Choose Outlook Anywhere Choose the Domain Admin for this Choose the defaults presented to you Give it a name Click Close Choose Migrate to Exchange Online Choose Cutover Migration Click Next Give the migration batch a name and click Next Leave all default and click Next It is syncing A notification is also made. Status is validating. The next stage. You must wait until Status = Synced. It has completed. Four mailboxes are synced and two distribution groups finalized. If you check details you will see that my mailboxes are ‘Synced’ and the distribution groups are ‘Completed’. If you don’t need to migrate those distribution groups you can delete them after migration or “mail disable” them in Exchange Manager on the SBS 2008. I received an email that confirmed the migration was successful. 4. Change DNS to point to Office 365 You will need to make a lot of changes to your public DNS records. Logon to the Office 365 admin portal and choose ‘Domains’ and click on the domain that should be your default mail domain. If you click on that domain a list with DNS records will show up and you must change or add those in your public facing DNS. How you do that is outside of the scope of this tutorial, each DNS provider looks different. From now on you can continue with How to migrate from SBS 2008 to Windows Server 2016 (Essentials) | How to uninstall Exchange Server 2007 on the old SBS 2008 . Once that is uninstalled go to a client that is properly connected to your network and delete the Outlook Profile and create a new one. You will see that it connects to Office 365 and your mail has been migrated.