moving on prem exchange mailboxes to 365 from windows server standard FE

i have a very old 2008 standard server FE
i have just signed up to O365 with email
What is the best method to migrate my 12 mailboxes?
Should i setup as hybrid and some sort of directory sync
We will keep the server to it dies then maybe just replace it with a cheap server or desktop
or is there other options like AD in the cloud etc
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Alan HardistyCo-OwnerCommented:
There is a direct Migration Wizard under the Exchange Admin Centre.  You need to make sure Outlook Anywhere is working and that you have a valid 3rd party SSL Cert installed on your server or the migration won't work.

It's relatively easy to migrate, and free!

Once in the Exchange Admin Center in the 365 Portal, under Recipients, go to Migration and follow the Wizard (Click on the + symbol and select Migrate to Exchange Online), fill in the relevant details and if all is good, it should complete happily.  Start the Migration Batch.

You can use to verify if all will work smoothly using the Outlook Connectivity test.

Once the sync is under way, plan to complete the switch over a weekend by changing the DNS records to point the MX records to 365, then block inbound port 25 to the server to prevent further emails arriving on the server and leave the Sync / Migration Batch running for at least 24 hours after blocking the port to catch everything.  Also advise users to stop sending emails over that weekend or they may get lost.

Once 24 hours is up, you should be able to stop the Sync / Migration Batch, then deleted the Migration Batch.

Then disable mailboxes on your server (don't delete them as it will delete the AD users too) and then delete the autodiscover virtual directory on the server using Exchange Management Shell:

get-autodiscovervirtualdirectory | remove-autodiscovervirtualdirectory

Then on the Monday (or on the Sunday if you feel so inclined), create a new profile in Outlook (don't delete the existing one for safety's sake) and setup the new 365 mailbox and let the mail suck down.

That should get you migrated.

There is a guide available too for this which you can follow here:

dougdogAuthor Commented:
so we will always still need a server on site running AD?
Alan HardistyCo-OwnerCommented:
Yes - if you want to keep computers as part of a domain for file-level permissions to documents etc, then AD is a great way to manage and also very handy for computer management using Group Policies, but if you plan to ditch the server in favour of a NAS for example, then you can kill the AD server and rely on NAS file / folder permissions, migrating the user profiles on the computers to a Workgroup.

All depends on what direction you are taking the users, but you will lose some good features if you ditch AD.
Determine the Perfect Price for Your IT Services

Do you wonder if your IT business is truly profitable or if you should raise your prices? Learn how to calculate your overhead burden with our free interactive tool and use it to determine the right price for your IT services. Download your free eBook now!

dougdogAuthor Commented:
the migration wizard is for migrating the users from on prem to cloud
but i mean the steps needed to get the 2 servers seeing each other
do i not need to install hybrid wizards etc
Alan HardistyCo-OwnerCommented:
Depends what you are planning.

What are you hoping to do?

With 12 users, I would just move everything to 365 as it will be easier to manage.  If you plan to sync AD and 365 passwords so that you have a single sign-on for both, you'll need AD locally and an AD server somewhere in the Cloud for redundancy because if your local AD server goes down, without a cloud-based server, no-one will be able to login to 365.  This route is more complicated and costly and for 12 users, questionably worthwhile.

dougdogAuthor Commented:
so the directory sync isnt included by default?
or the Azure AD?
do i just add in my domain
add the dns records
and migrate email
Alan HardistyCo-OwnerCommented:
By default - no.  If you want password sync for 12 users, it's a lot of extra work for very little gain.

Personally, I'd just perform a cutover migration (as per my initial post) and then migrate everything off your server.  You can set strong passwords on 365 and then set them to never need changing, set Outlook to remember the passwords and then you'll never need to know the password again.

Worst case, you reset a password down the line, update Outlook and any mobiles and then forget about it until they can't remember it again, then repeat the process.  For 12 users, this is the simplest, easiest approach.  If you had hundreds / thousands of users, then I'd seriously consider AD sync.

dougdogAuthor Commented:
so to migrate the mailboxes no link is needed
it does it all over the internet

do i just add my domain inside domains in 365
Alan HardistyCo-OwnerCommented:
Once you have setup the admin account in 365, add your domain, verify ownership (add a TXT Record in DNS), then setup the migration batch (sorry for neglecting to mention adding the domain), then start the migration and if you're lucky, you might be finished ready for this weekend, but more likely you can plan to cut over next weekend.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
dougdogAuthor Commented:
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today

From novice to tech pro — start learning today.