We help IT Professionals succeed at work.
Get Started
Research Question

Exchange 2010 to Office 365 and new server (SBS 2011 to WS2019)

Last Modified: 2021-01-11
All, I'm in the process of upgrading our server.
We've got an SBS 2011 server (built-in Exchange 2010), and moving to new hardware and Windows Server 2019.  We've got about 45 users.
I'm using server-essentials.com to do the server migration itself, this seems to be going great so far.
I'm planning to do a cutover migration for the email, and start this after hours on 24th December.  Our Exchange 2010 store is 180GB in size and we have a 100MB upload connection, so I'm hoping this will be complete by the 27th.  
I had some questions
1) I already have a 365 tenant account configured for the company.  We used Microsoft Teams on their free licence, so there are already some users in the tenancy.  I take it that when the sync begins, the fact that there are already users (not with mailboxes though) in the 365 tenancy won't cause any problems?
2) I was just planning on using the basic Microsoft method of migrating.  I know that there are third party tools like CodeTwo, BitTitan MigrationWiz etc.  Is there any benefit to purchasing one of these, is it going to be made much easier?
3) I read that when doing the Migration batch transfer, that it is recommended to shut port 25 on the server, so there are no incoming emails which would make it into Exchange 2010 once the mailboxes had been cutover to 365.  The problem is that we have a managed Cisco router through BT at this site, any requests for ports to be closed/opened have to be made in advance and there is no guarantee when this will be actioned over the holidays.  Can I simply block it on the SBS firewall?
4) From what I can see, the migration creates users on the tenancy with the mailbox contents, then I have to assign the licences.  Do they take the password from the SBS 2011 or do I need to create new passwords?  I have some of their passwords but not all.  I can SMS them information if need be.
5) Phones, we have around 20 users who access emails on their phones.  I would like to be able to send out a notification in advance so that when their existing email stops syncing, that they can update their settings.  What's the best practice here - ask them to download the Microsoft Outlook app, and is there somewhere in the tenancy where I can find out in advance what the new server settings will be?
6) All of the desktops (about 35 or so) in the organisation will be left switched on and I can remote into any of them.  They are running Office 2010 so will all need to be upgraded to the new desktop apps.  Do I have to remote into all desktops to do this, or is there an easier way?
7) Some will have archive.pst files on them, so ideally I'd like to make sure we don't lose any of these.
Once the cutover migration is complete for the email, I'm planning to finish the SBS 2011/WS2019 upgrade the following week, so that everything is working as normally as possible when they come back from their break.
Any pointers welcome.
Thanks, Alex 
Watch Question
Solutions Architect
Top Expert 2016
This problem has been solved!
Unlock 1 Answer and 9 Comments.
See Answer
Why Experts Exchange?

Experts Exchange always has the answer, or at the least points me in the correct direction! It is like having another employee that is extremely experienced.

Jim Murphy
Programmer at Smart IT Solutions

When asked, what has been your best career decision?

Deciding to stick with EE.

Mohamed Asif
Technical Department Head

Being involved with EE helped me to grow personally and professionally.

Carl Webster
CTP, Sr Infrastructure Consultant
Ask ANY Question

Connect with Certified Experts to gain insight and support on specific technology challenges including:

  • Troubleshooting
  • Research
  • Professional Opinions
Did You Know?

We've partnered with two important charities to provide clean water and computer science education to those who need it most. READ MORE