Migration of Exchange 2003 to Office 365 E3

Dennis Pillow
Dennis Pillow used Ask the Experts™
I am going to attempt a migration of Exchange 2003 to Outlook 2019 on Office 365 E3. Looking forward to any advice.
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PowerEdgeTechIT Consultant
Top Expert 2010

How many users? Just as a general starter to the conversation, I might recommend a tool like BitTitan's MigrationWiz ... Makes moving mail easy. Depending on your Internet connection and number of users, I would use the Office Deployment Tool to deploy the Office 365 software locally rather than streaming the installation over the Internet for each machine.
Jose Gabriel Ortega CastroCEO Faru Bonon IT /Top Rated Freelancer on Upwork / Photographer
Awarded 2018
Distinguished Expert 2018

Hi Dennis!

* Be careful with the terms, you can't migrate Exchange Server 2003 (which is a Server application) into Outlook 2019 (which is just the email client used to connect to the server.

* I will propose you 3 path, you select the one you prefer.

Path1. Double Migration Mode.
Install Exchange server 2010, migrate from 2003 to 2010 all mailboxes,
Decomision 2003.

Note I think that from here you can directly move from 2010 to O365

Second migration is to use the exchange 2010 to upgrade it to 2016

And well there you go in that link the step by step.

Path 2. Cutover migration from MAPI to O365
If you have less than 300 users you can use a cutover migration


Path 3. Use 3rd party software like MigrationWiz
Get migrationwiz license (1 for the mailbox) and let the software on cloud do the job.
Technical Consultant
If you 'double step' the migration make sure you go to Exchange 2010 SP3 (with all the CU updates on it!) like this

Personally I'd use a third party tool as suggested, I've used date Quest migration for Exchange tool it's quite cheap about 12 dollars per mailbox, the problem with using third party tools is they wont repoint your Outlook clients to Office 365 - Quest says it can, but it fails miserably. so if you have a lot of clients then the double migration is the way to go.
AmitIT Architect
Distinguished Expert 2017

If user count is low, you can do cutover migration. Else you have to do hybrid migration or you might need to use some 3rd party tool. Personally, i haven't used any 3rd party, so cannot give you much advise. Hybrid, i have done several times.

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