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Migrate from SBS2011 and Exchange 2010 and change domain name

My current setup is running under VMware ESXi 6.0 -

• SBS 2011 - PDC, Web, DNS, Exchange
• Windows 2012R2 - DC, DNS. With Azure AD sync for users to 365 for SSO and Office

These are on a DDNS domain that I don't own as static IPs weren't easily back then in my area.

 

I also use a separate email server (on my web server host) that receives emails and forwards to my Exch server - It receives for 3 domains I own forwards to appropriate accounts on the DDNS Exchange server. The Exchange server sends from those domains via a third-party smarthost to avoid being seen as spam from a non-static IP.

 

I now have a static IP.

 

Due to end-of-life of SBS2011, I want to upgrade to Server 2019 and Exchange 2019 (or 365).

But, at the same time, I'd like to use a proper domain that I've setup and pointed to my external IP (mail2.domain.com) rather than the old DDNS (domain.ddnshost.com).

My SSL Cert is currently for the ddns domain.

 

I was originally looking at the MS Express or Cutover migratiions to 365, but the first step requires that you prove ownership of the On-Premises domain

• https://docs.microsoft.com/en-au/exchange/mailbox-migration/cutover-migration-to-office-365#step-1-verify-you-own-the-domain
• https://docs.microsoft.com/en-au/exchange/mailbox-migration/use-minimal-hybrid-to-quickly-migrate#step-1-verify-you-own-the-domain

This seems to make those migraations impossible for me.

 

I'm looking for some advice on where to start ... Even OK with paying someone for some help with pointing me in the right directions.

 

Regards

 

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• AD Domain Services
• DNS
• Exchange Server 2010
• FSMO
• Migration
• AD Certificate Services
• SBS 2011
• SSL Certificate

asked07/09/2019 09:37

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  Hello Mike,

  The guides needed to accomplish your task are:

  • How to migrate SBS 2011 to Windows Server 2019 Standard, Datacenter or Essentials
  • Cutover migration from Exchange Server 2010 on an SBS 2011 Standard to Office 365

   

  For the certificate needed we can use Get a free Let’s Encrypt SSL certificate for Access Anywhere and automatically renew it. Though this method does not work on SBS 2011 (Certify the Web needs .Net 4.7.2) we can run this on your new Windows Server 2019. We generate a certificate for any domain you own, export that to a pfx file and import it in the SBS 2011 for the time you do the migration. This is a workaround I always use to get certificates for free and who does not want that :)

   

  You need a valid domain name + static IP address, there is currently no other way you can migrate to Office 365. There is one other 'option' and that is the export procedure described here Export mailboxes from Exchange Server 2010 to pst files. You will use the pst files to later import those into O365 but that is really only meant for just a few mailboxes and those should not be 'huge'.

   

  If you signup for https://server-essentials.com/store/sbs-2011-migration-kit-silver-office-365 (updated link to correct migration kit) and add one-hour extra support I will help you get this done. We will connect with Microsoft Teams (former Skype) + Teamviewer so that we can discuss and work on anything you want me to help you.

  Kind regards
  Mariëtte

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  answered 07/09/2019 10:11

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